230 Questions to Ask Your Boyfriend That'll Strengthen Your Connection

A couple smiles at each other while lost in a deep conversation.

  • Sarah is the Entertainment & Celebrity Editor for The Knot, with special focuses on pop culture and celebrity wedding news.
  • Before joining The Knot Worldwide, Sarah was a contributing writer for Bravo at NBC Universal.
  • Sarah has a degree in journalism and resides in New York City.

It doesn't matter whether you and your boyfriend have been dating for five days or five years—there is always something new you can learn about each other. There's a good chance you've covered the basic information over your first few dates (like where you're from, how many siblings you have, and what your favorite TV show is, to name a few things). We're of the mindset, though, that there's no such thing as having too many questions to ask your boyfriend. In order for your relationship to flourish and thrive, it's important to know your partner inside and out. After all, understanding their core values and beliefs is a key indicator of how compatible you are. That's why we've compiled the ultimate list of things to ask your boyfriend . Here, you'll find 230 deep, fun and juicy questions to ask your bf, spanning a variety of thought-provoking topics and subjects.

Types of things to ask your boyfriend in this article:

Deep Questions to Ask Your Boyfriend

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The hard questions to ask your boyfriend are sometimes the most interesting. While it may seem intimidating, one of the best ways to strengthen your emotional intimacy is to simply go there. If you tend to avoid asking the tough Qs, you aren't alone—but we are here to help you get over that fear. Use this list of deep questions to ask your boyfriend to take your connection to the next level.

  • What makes you happy?
  • When do you feel most fulfilled?
  • How would you define success?
  • Do you consider yourself successful?
  • Do you consider yourself happy?
  • Are you proud of your accomplishments thus far?
  • Where do you see yourself in five years?
  • What do you look for in a friend?
  • How do your friends make you feel?
  • What was your childhood like?
  • Would you change anything about your upbringing?
  • How did your parents impact your view on love and relationships?
  • What gets you out of bed in the morning?
  • What's your biggest fear? Do you think you could face it?
  • How important is religion do you?
  • What do you think happens after death?
  • Do you believe in a higher power?
  • What's the story behind your middle name?
  • What's the biggest misconception people have about you?
  • Did you ever have to break up with a friend? How did it go?
  • Have you ever had your heart broken?
  • Do you think a relationship can come back from cheating?
  • What's the hardest decision you've ever had to make?
  • What's the biggest risk you've ever taken?
  • What's your favorite quality about yourself?
  • Who are you closest to in your family?
  • What do you think are the most important qualities of a healthy relationship?
  • Who is someone in your life you know you can always count on?
  • What do you love about your mom?
  • What makes me beautiful to you?

Next time you need a question to ask your boyfriend when the conversation lulls, refer to this section. Not every conversation you have needs to be so serious. In fact, we'd guess one major reason you're dating your boyfriend is because of your shared humor, or his ability to make you laugh. That's why these fun questions to ask your boyfriend are just as important as the hard and serious ones.

  • Where should our next vacation be?
  • When was the time you laughed the hardest?
  • What's your favorite holiday?
  • What's your favorite holiday food?
  • What's one holiday tradition you think we should start together?
  • What's your go-to karaoke song?
  • What does self-care look like for you?
  • If you could craft the perfect five-course meal, what would each course be?
  • What was your favorite toy as a child?
  • Did you ever sleep with stuffed animals?
  • How do you like to spend a rainy day?
  • What does your ideal Sunday morning look like?
  • What's one movie you can watch over and over again?
  • What's your favorite time of year?
  • If you could pick a theme song for yourself, what would it be?
  • If there was a movie made about your life, what would the title be?
  • What actor would play you in that movie?
  • How do you feel about tattoos?
  • What was the best Halloween costume you ever had?
  • If you could live in any fictional town or city, which would you pick?
  • When you were a kid, what career did you want to have?
  • Who's your role model?
  • Would you rather time travel or read people's minds?
  • Who's your dream Super Bowl Halftime Show performer?
  • What's your favorite movie theater snack?
  • What are you most passionate about in life?
  • If you could start a non-profit, what cause would you support?
  • What do you like to do after work?
  • Are you a morning person or a night owl?
  • What does your perfect day look like?

Who doesn't love a gossip session? When you think you know absolutely everything about each other, come to this list of juicy questions to ask your boyfriend. We bet you'll learn something new about him when you start using these creative conversation starters .

  • What's your most embarrassing moment?
  • Which celebrity would leave you starstruck in real life?
  • What's your guilty pleasure?
  • Do you talk to yourself?
  • Do you sing in the shower?
  • What do you think is more important: an emotional connection or a physical connection ?
  • What was the last thing you searched on Google?
  • Do you believe in astrology?
  • Do you believe that every person has one soul mate?
  • Do you think it's possible to fall in love at first sight?
  • If you could go on any reality TV competition show, which would you pick?
  • If you started a podcast, what topic would it be on?
  • What's the last book you read for fun?
  • What's the craziest dare you've ever accepted during Truth or Dare?
  • What's one fact no one else knows about you?
  • Do you believe in ghosts?
  • What's a hidden talent you have that you never get to show off?
  • Who's your favorite person in your life?
  • Do you ever feel like you lived a past life?
  • If you could go back in time and live in any historical era, which would you pick?
  • If you could host a dinner party with any famous person, who would it be and what would you talk about?
  • Do you think men and women can ever just be friends?
  • What are your relationship deal breakers ?
  • What's the craziest thing you've ever gotten the "ick" from?
  • Is there anything you wish you could change about yourself?
  • Is there anything you wish you could change about me?
  • If you could change your name, would you?
  • If there was a book with one page written about every day in your life, would you read the whole thing?
  • What do you think your best attribute as a boyfriend is?
  • Can you list ten authors who aren't men?

What are good questions to ask your boyfriend? We're so glad you asked. These light-hearted quips will help you two go beyond the surface level. Plus, there's a good chance these cute questions to ask your boyfriend will give both of you butterflies, so have a few of them ready to go for your next date night.

Couple taking a bike ride in Denver

  • What's your favorite memory we've made together?
  • What's one thing we haven't done yet that you're excited to do with me?
  • What's a hobby you think we should try together?
  • Do you like when I cook for you?
  • Do you prefer cooking for me?
  • Have you imagined what our future house would look like?
  • Do you prefer spontaneous or planned date nights?
  • Do you prefer fancy or casual date nights?
  • Do you think we spend enough time together?
  • Do you like getting breakfast in bed?
  • What's been the best year of your life so far?
  • What's something you're passionate about that you never get to discuss?
  • Did you ever have a crush on a fictional character?
  • What was your first kiss like?
  • What's your favorite love song?
  • Have you ever kissed someone under mistletoe?
  • What's the craziest thing you've done to impress someone?
  • Do you like talking on the phone?
  • How do you like to be treated when you're sick?
  • What's the best gift you've ever received?
  • Can you think of two people in your life who have a relationship you look up to?

Knowing how your boyfriend expresses (and wants to receive) love is crucial for the longevity of your relationship. Prioritizing these romantic questions to ask your boyfriend will make him feel special and valued, because making the effort to show you care about what makes him happy is priceless.

  • How would you define falling in love?
  • When did you know you were in love with me?
  • What's your love language ?
  • How do you like to express love?
  • How do you want me to express love to you?
  • Do you like being surprised by random gifts?
  • What does your ideal date night look like?
  • What's your favorite date we've ever been on?
  • If you could plan a date for us anywhere in the world, where would we go and what would we do?
  • What do you think about public proposals?
  • Do you think couples should talk about engagement rings before they get engaged?
  • Have you ever thought about what you want your wedding to look like?
  • Do you like surprises?
  • Do I make you feel heard?
  • Do I make you feel valued?
  • What's your favorite thing about our relationship?
  • What's something I can do to make our relationship better?
  • Do you think we have healthy emotional intimacy?
  • Do I show up in your dreams?
  • Is there anything you've ever wanted to teach me?

We've covered fun, cute and serious things to ask your boyfriend—but we'd be remiss if we left out a few spicy Qs too. You might be someone who loves going there with your partner, in which case, you've probably covered these questions already. But for those who find it a little bit awkward to talk about intimacy and sex, you aren't alone. Instead of stressing about what to say, use this list of dirty things to ask your boyfriend when you're in the mood to spice things up.

  • Are you satisfied in the bedroom?
  • What's something we've never tried together that you want to?
  • Do you wish we used more sex toys together?
  • What's a fantasy of yours we've never talked about?
  • What's your favorite type of kiss?
  • Do you like PDA?
  • Do you like getting spicy texts?
  • How many times do you think couples should have sex a week?
  • What non-sexual act turns you on the most?
  • Do you like when I wear lingerie?
  • Do you like wearing lingerie?
  • Do you wish I was more affectionate?

While not quite as juicy as the dirty questions for your bf above, these serious ones are just as critical. While they may not be questions you want to whip out on, say, your first date, these topics are important to discuss early in your partnership to evaluate your compatibility.

  • Do you see yourself getting married one day?
  • What qualities do you think are most important in a spouse?
  • Do you envision yourself having kids?
  • What kind of parent do you want to be?
  • Why did your last relationship end?
  • What was your longest relationship?
  • Do you still keep in touch with your exes?
  • Would you sacrifice your career goals for love?
  • Do I do anything that bothers you?
  • Do you think I'm living up to my potential?
  • How do I make you feel when we hang out with your friends?
  • How do I make you feel when we hang out with my friends?
  • What does your average work day look like?
  • Are you friends with your coworkers?
  • When was the last time you voted?
  • Are you an introvert or an extrovert?
  • How do you handle anger?
  • Do you get jealous?
  • What do you do when you feel stressed?
  • What's your favorite part about being an adult?

Flirting is essential, especially if you want to maintain the honeymoon phase for weeks, months, and even years into your relationship. Refer back to this roundup of flirty questions to ask your boyfriend when you want to reignite the spark.

  • Do you remember what I wore on our first date?
  • Do you like when I wear perfume/cologne?
  • What color should I wear more?
  • What's your favorite physical attribute of mine?
  • What's your favorite physical attribute of yours?
  • What did you like most about me when we first met?
  • What do you like most about me now?
  • What gives you butterflies?
  • What do I do that makes you laugh?
  • What's your favorite inside joke we have?
  • There are eight billion people in the world. Why are you with me?
  • Will you dance with me right now?
  • How many times did you want to ask me out before you did?
  • What color do you associate me with?
  • Do you think about me during the day?
  • What was our first kiss like for you?
  • If I was sad, how would you make me feel better?

When you think of good questions to ask your boyfriend, your mind probably goes to the serious ideas we've already listed above. We're of the mindset, though, that random questions are just as valuable. (At the very least, they're way more fun than the hard questions.) These obscure and funny things to ask your bf are ideal for when you need something new to talk about. Thank us later.

  • What's the craziest conversation you've ever overheard in public?
  • What's your favorite scent?
  • What candy do you think is overrated?
  • What's the last movie that made you cry?
  • Who's the most surprising musical artist you love?
  • What song could you listen to on repeat forever?
  • What's your biggest pet peeve?
  • If you could pick up and move to an entirely new city, where would you go?
  • If you didn't have to work for an entire year, what would you do with your time?
  • Do you watch the news?
  • What was your favorite subject in school?
  • If you could go back and relive any day of your life, which one would you pick?
  • What food or drink could you never live without?
  • What's your biggest hot take?
  • What's your comfort TV show?
  • What do you think is the weirdest habit you have?
  • Have you ever used a pick up line ? Was it successful?
  • Do you believe in aliens?
  • Do you believe there are sea creatures we haven't discovered yet?
  • Would you ever run for President?
  • Do you ever snoop on people's phones in public?
  • If you could adopt any skill without practicing, which would you pick?
  • What's one meal you wish you could make perfectly?
  • What's your favorite amusement park activity?
  • What's your gas station snack combo?
  • What was your favorite school lunch as a kid?
  • Would you go to space if you had the opportunity?
  • What do you think is the best outfit in your closet?
  • Do you make your bed every morning?
  • Would you rather be right or happy?

We can't complete our list of good questions to ask your boyfriend without highlighting the most significant ones. These questions get to the core of who your boyfriend is—and we'd argue that you don't truly know each other until you talk about these topics. When you're ready, bring up these important questions to ask your boyfriend. You never know what more you'll learn.

  • How do you think responsibilities should be divided in a marriage?
  • How do you identify politically?
  • Do you think it's ever okay to lie? In what circumstances?
  • Would you speak up if I do something that offends or upsets you?
  • What's a relationship mistake you made in the past that you don't want to repeat?
  • Do you think people ever truly change?
  • Does your family have any cultural values or traditions I should know about?
  • Do you think we fight fair?
  • Do you think couples should have shared financial power in a relationship, or should it fall to one person?
  • Would you rather be a stay-at-home parent or a working parent?
  • Do you expect dinner to be ready for you when you come home from work? What happens when both of us are working?
  • Has anyone ever made you feel belittled at work? What about in your personal life?
  • Do you think it's possible to stay in the honeymoon phase forever?
  • How do you think couples can keep the spark alive in a long-term relationship?
  • Do you feel like there are gender or societal pressures in our relationship?
  • Would you ever go to couples therapy?
  • Do you trust me?
  • Do you feel safe in our relationship?
  • What's something we could change about our relationship to make it stronger?
  • Can you see yourself getting married to me?

couple grabbing coffee questions to ask your partner

The Winding Road Tripper

Road Trip Questions For Couples: 149 Fun and Deep Conversation Starters

This post may include affiliate links. As an Amazon Associate, I (The Winding Road Tripper) earn from qualifying purchases.  Read more . 

What better time than a road trip to get to know your partner a little bit better?

These road trip questions for couples will get you laughing, talking, and wondering where the time went on your long drive. 

Use these road trip questions as a game or simply a way to get the conversation started. 

This list of 149 road trip questions provides a variety of topics and types of questions, so you’ll be sure to find questions to keep you and your partner entertained on your long car ride . 

Travel Road Trip Questions

While you’re traveling on the road, it only makes sense that you’d stop to ask some questions about traveling itself.  These questions can get philosophical, or they can be as lighthearted as you need them to be.

  • What is your favorite travel memory from your childhood?
  • Where would you go if you could go anywhere from a fictitious location, a destination from history, or a real-world location from the present day?
  • If you could bring any one thing from home that you wouldn’t normally be able to take on a road trip, what would you bring with you? 
  • What’s your favorite part about traveling?
  • What is your least favorite part about traveling?
  • Is there somewhere you’ve always wanted to go?
  • Would you ever go on a big vacation with both of our families?
  • If we could each bring one friend with us on this road trip, who would we take?
  • If you could live in a van and always be on a road trip, would you do it?
  • What’s the strangest thing you’ve ever seen while traveling? 

Deep Thought Provoking Road Trip Questions

The road trip you’re taking is more than just about exploring the world around you; it’s also about exploring how each other sees the world. A journey with your partner down a long and winding road is the perfect opportunity to ask thought-provoking questions. These questions will act as springboards to get the two of you talking about some introspective topics.

  • If you never had to work your day job ever again, what would you do with all of your time? Is there a way that you can bring some of that into your life?
  • What’s one of the biggest societal issues that impacts and shapes your everyday life?
  • What is life like from the perspective of a tree? Is there a way to talk about the world outside of the human context? 
  • When was the last time you tried something new? What was it?
  • Do you feel that you’re challenged enough in ways that help you grow?
  • What’s one life lesson you learned the hard way?
  • What’s one life lesson you learned the easy way?
  • If you could only fix one societal issue, which one would it be? 
  • What makes art “art?”
  • What moment in your life has had the biggest impact on where you are today? 

Funny Road Trip Questions

If the drive is starting to get long or there’s a lull in the conversation, try funny road trip questions for couples to liven things up.

  • Would you rather fight one elephant-sized chicken or 100 chicken-sized elephants?
  • If vegetables could talk, which one would be your least favorite?
  • Which Olympic game is most improved by having the athletes get incredibly intoxicated beforehand?
  • You’re stranded on a desert island with a lifetime supply of one product. What is the single worst product to be stuck with? 
  • What are some of the funniest memes, jokes, and trends you remember from high school?
  • Is cereal a soup? Is a hotdog a sandwich?
  • Can you say something sexy in the least sexy voice you can come up with? 
  • What secret conspiracy would you like to start? 
  • When we’re in our sixties, what are we going to be nostalgic for from our teen years?
  • Toilet paper: Over or Under?

This Or That Road Trip Questions

This or That questions give your partner a choice between two options. You can use these questions as fun get-to-know-yous or challenge your partner with some tough choices. 

  • Arrive early or arrive late?
  • Family or friends?
  • Comedy or drama movie?
  • Night out or night in?
  • Home-cooked dinner or dine out?
  • Big family or small family?
  • Expensive wedding or intimate wedding? 
  • Plan ahead or be spontaneous? 
  • House party or dinner party?
  • Cats or dogs?

Would You Rather Questions

Would You Rather questions of the ultimate way to put your partner to the test. These questions are designed to put someone in a tough spot choosing between two difficult options. These road trip questions make for a great game, so try taking turns and see who can come up with the most interesting responses. 

  • Would you rather always be overdressed or underdressed?
  • Would you rather be able to travel back in time and tell the 10-year-old version of yourself any one thing or be able to travel forward in time and have the 90-year-old version of yourself tell you any one thing?
  • Would you rather be the star of an Academy Award-winning movie or a cult movie classic?
  • Would you rather be wealthy we’re happy with where you are in life?
  • Would you rather go to a luxury resort or go camping?
  • Would you rather have all the latest technology or be an outdoors expert?
  • Would you rather live in a library or in a theme park?
  • Would you rather travel everywhere by helicopter or on horseback? 
  • Would you rather be a bad actor or a bad musician?
  • Would you rather always be alone or always be in a big crowd? 

Just like the Marvel Comics classics, what if questions take your partner and place them in an alternate reality. These questions can explore deep topics or be ridiculous. 

  • What if you woke up tomorrow and had all of the powers, and weaknesses, of your favorite comic character?
  • What if you found out that I had magic powers and I’ve been keeping my double life as a witch or wizard a secret?
  • What if I inherited a mysterious and haunted mansion from a long-lost relative, but we had to stay there together for one month straight to keep it? 
  • What if we suddenly switched bodies?
  • What if you found out that I had been a millionaire this whole time? 
  • What if you found out that you could time travel?
  • What if you got your dream job, but you had to move to a different country?
  • What if aliens landed tomorrow, but they looked and acted just like me?
  • What if we aged in reverse?
  • What if our car could talk and had its own personality? 

Silly Road Trip Questions That Can Get Serious

Sometimes the line between silly road trip questions for couples and a serious question is just the mood in the room. We’ve got a few questions for you that can fall either way and let you test the conversational waters. 

  • If you inherited a billion dollars when you were fifteen, what do you think you would have done with the money?
  • What’s the first thing you do if we wake up tomorrow morning and all of a sudden every animal on Earth can speak and understand our language?
  • You can go back in time and change one thing about history, but it can’t be a major historical event, what do you change?
  • Your most ridiculous fear comes to life, what happened?
  • How would society change if everyone could suddenly fly?
  • What would your job be in the zombie apocalypse?
  • Would you take a one-way trip to Mars to be one of the first humans to live on another planet? 
  • What would you do if aliens landed on the planet and thought you were the leader of Earth?
  • Would you replace all weapons on the planet with their Nerf equivalent?
  • Would you want to live for free in a historically preserved building, but you can’t add modern necessities like Wi-Fi?

Get To Know Each Other Road Trip Questions

One way of looking at a road trip is that you and your partner will be sitting in the same room together for a very long time. So this is a great time to get to know each other a little better.

  • Have they ever been in love before?
  • Do you have a secret dream that you wish you could make real?
  • What was the most trouble you got in as a kid? 
  • Who is your favorite author?
  • Do you have a personal hero?
  • Has anyone ever inspired you to live a better life?
  • Do you want to have a big family or a small family?
  • What are your hobbies?
  • If you could only eat one meal for the rest of your life, what would it be?
  • Do you prefer romantic surprises or planned nights out? 

Road Trip Questions About Firsts

Road trips are all about firsts, and there’s no better time to ask your partner about their firsts when you’re out on the road. 

  • Who was your first crush?
  • What was the first time you had to deal with a real adulthood responsibility in your life? 
  • What’s the first book or movie you remember enjoying as a kid? 
  • Who was your first kiss?
  • What was the first concert you went to?
  • What was your first place that wasn’t living with your parents?
  • What was your first job? 
  • What was the first time you felt that you had accomplished something good?
  • Who was there for you when you went through your first heartbreak?
  • Do you remember your first day of school? 

Quiz Questions For Couples: How Well Do You Know Me

Keep these quiz questions light-hearted, but if a serious topic comes up, don’t be afraid to use your time together on the road trip to get to know each other. 

  • What’s the name of the band or artist that I wouldn’t let anyone catch me singing along to?
  • What’s the one movie or TV show I could watch on repeat for the rest of my life?
  • What’s my favorite way of spending time with you?
  • What’s my favorite part about you?
  • What’s the fastest way to cheer me up when I come home from work upset?
  • What is my biggest pet peeve?
  • Would I rather stay in and watch Netflix or go out and try something new?
  • What is my favorite outfit?
  • Which family member do I have the best relationship with?
  • If we could only spend one more day together, what would I want to do?

Explore Your Partner’s Favorite Topics

One of the best parts about getting to experience a road trip with your partner is spending all that time getting to know each other.  This time together gives you a chance to explore your partner’s favorite topics and let them take the reins of the conversation for a while. Be ready with follow-up questions to keep it going! 

  • What’s your favorite hobby and how long have you been into it?
  • Tell me more about your favorite genre of music and what about it you like the most?
  • What’s the best movie you’ve ever seen?
  • Who’s your favorite sports team?
  • What do you like most about your job and what do you like the least?
  • What’s your favorite way to relax over the weekend?
  • Do you have a hobby that you wish you could spend more time on?
  • Do you have a favorite podcast?
  • What is your favorite time of the year?
  • Do you like the city we live in or would you rather move somewhere else? 

Family History Questions For Couples 

There’s something that’s always just a little bit historical about a road trip. As you drive through the boundless highways and those old city streets, ask your partner some questions about their family history. 

  • Do you have any famous family members?
  • How far back can your family trace their history?
  • What’s something about your family that I would have never thought to ask about? 
  • Do you have any relatives that you wish you could spend more time with?
  • Did your parents have any alternate names they were considering when you were born?
  • Does your family still live in your hometown?
  • What nationalities and ethnicities make up your family background?
  • Does your family speak any languages besides English?
  • Do any of your family members live in different countries?
  • Be honest, how comfortable are you at big family events like Thanksgiving or Christmas? 

Questions That Make Memories

Whether this is the first road trip with your partner or the 30th, you’re making memories while you’re putting miles on those tires. Now’s a good time to ask some questions that will make as many memories as the road trip itself.

  • What’s the first thing you noticed about me?
  • When we first started dating, what did you tell your friends about me?
  • What are you looking forward to the most on our road trip together? 
  • When was the first time you mentioned our relationship to your family?
  • What is your favorite thing that I do for you?
  • Was there one moment when you realized that I was the one for you?
  • What was your favorite date that we ever went on?
  • What did you really think of my family when you first met them?
  • What did you think about our first night together that next day?
  • When you first walked into my place, what did you think of it?

Road Trip Questions That Keep The Adventure Going

The way back home is still part of the adventure. These are a few questions that you can ask as you complete the final leg of your road trip together. 

  • If we could change plans and drive anywhere right now, where would you want to go?
  • What’s something you’ve always wanted to do on a road trip?
  • Do you have any favorite road trip games or activities from when you were a kid?
  • What was your favorite destination on our trip?
  • Is there a place you’d like to go to again?
  • What was your least favorite place on our trip?
  • Where do you want to go for our next road trip?
  • If you could rent any kind of car for our next road trip, what would it be?
  • What’s one thing you wish we could have done on this road trip?
  • Should our next road trip be longer or shorter?

The Road Trip Book Club Question Session

Here’s a great way to add some more fun to your road trip as well as give you fodder for limitless questions and discussions. All you need to do is pick out a book that you’ll both like and use these questions as prompts for a book club built for two. 

  • What about this book stands out to you the most right now?
  • If you could change one thing about what we’ve read so far, what would it be? 
  • Who’s been your favorite character so far in this book?
  • What’s been the least believable thing a character has done?
  • If you can have one character join us on this road trip, who would it be? 
  • Would you want to go on a road trip in the world of this book? 
  • Has there been anything you don’t like about this book?
  • What do you think of the author’s writing style?
  • Would you want to read another book by the author? 

More Road Trip Entertainment Check-Out: Road Trip Activities for Adults: Fun Ideas for a Long Car Ride 15 Ridiculously Fun Road Trip Games Best Podcasts for a Long Car Ride Best Audiobooks for a Road Trip Road Trip Game Apps to Keep You Entertained 20 Intriguing Road Trip Trivia Questions

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101 questions to ask your boyfriend to really get to know him—from sweet to sexy.

Sarah Regan

You might think you know your boyfriend, but when was the last time you asked him about his childhood, his dreams, or even his biggest turn-on?

In any relationship, it's so important to stay curious about your partner , continuously getting to know them and never assuming you have them all figured out. Whether you've been dating for a few months or a few years, here are 101 questions to ask your boyfriend to get to know him and deepen your connection.

Deep questions to ask your boyfriend

  • What do you wish you had more of in your life right now?
  • What do you wish you had less of in your life right now?
  • Do you want to be more or less like your parents?
  • When was the last time you cried?
  • Do you talk about your feelings often? Why or why not?
  • Who do you feel most comfortable talking about your feelings?
  • Who do you feel least comfortable talk about your feelings with?
  • What would you be doing if money wasn't a concern?
  • What do you want to be remembered for after you die?
  • What's more important: science or art?
  • What's your relationship to your gender?
  • What does masculinity or being a man mean to you?
  • What gender stereotype do you wish the world would let go of?
  • What does friendship mean to you?
  • What do you think is the meaning of life?
  • Have you ever been to therapy?
  • What's your relationship with your parents?
  • What were you like in high school?
  • What's your relationship to religion?
  • Are you a spiritual person ?
  • What parts of yourself are you working on right now?
  • Do you want kids? Why or why not?
  • Do you have any big regrets in life?
  • What feeling have you been experiencing the most lately?
  • Is there something you care about for which you would be willing to risk your life?
  • What is one dream you’d like to see come true this week/month/year?

Relationship questions to ask your boyfriend

  • What does it mean when you say "I love you" to someone?
  • Do you believe in the concept of soul mates?
  • Is jealousy healthy in a relationship?
  • Is lying ever OK?
  • Is cheating ever OK?
  • Have you ever cheated on someone before? Why did you do it—and do you regret it?
  • Have you ever been cheated on?
  • How would you feel if your partner made more money than you?
  • What was your last relationship like?
  • What's your usual approach to conflict?
  • Have you ever been in love?
  • What initially attracted you to me?
  • How long does it take you to open up to someone?
  • What's your  attachment style ?
  • How connected are you feeling in our relationship?
  • What could make our relationship even better?
  • What makes you feel most loved?
  • How can I be a better partner to you?
  • What makes you feel closest to me?
  • How have your parents affected the way you show up in relationships?
  • Is there anything in our relationship that you’re hoping will change in the future?
  • What’s one positive thing you’ve learned from me since we’ve been together?
  • What’s something you think I could learn from you?
  • Is there anything you haven’t told me because you’re afraid I’d judge you?
  • How can I better support you in your personal or professional life?
  • What is something you've always wanted to experience together?
  • What kind of father would you like to be?
  • What's one thing all of your former partners would agree on when it comes to you?
  • What does healthy love feel like for you?
  • What’s something your parents have taught you about love that you now realize is wrong?
  • What are your long-term goals for our relationship?
  • What do you fear about our relationship?

Fun questions to ask your boyfriend

  • Cat person or dog person?
  • Would you survive a zombie apocalypse?
  • Would you survive being stranded on a deserted island?
  • What's your favorite conspiracy theory?
  • What reality TV show would you be on?
  • What's your most annoying habit?
  • What's the most embarrassing thing in your search history?
  • What's your favorite type of music?
  • Best concert you've ever been to?
  • Worst concert you've ever been to?
  • Do you believe in astrology?
  • Do you relate to your astrological sign?
  • City or country?
  • Who's a celebrity that you think is overrated?
  • Who's a celebrity that you think is underrated?
  • What element do you resonate most with: fire, water, earth, or air?
  • What's the best gift you've ever received?
  • Where is the next place you'd like to travel?
  • If you were an animal, what animal would you be?
  • Who would you want to play you in a movie about your life?
  • What was your first email address ever?
  • What's your go-to karaoke song?
  • Can you sing a song describing what you think the inside of your brain sounds like?
  • If you had to give up one of your senses, which would you choose and why?
  • What’s a fun activity you enjoyed as a child that you continue to do now?
  • If you could only eat one meal for the rest of your life, what would you pick?

Flirty & dirty questions to ask your boyfriend

  • What are your thoughts on pornography?
  • Morning sex or sex at night ?
  • Have you ever fantasized about me?
  • What's an unusual thing that turns you on?
  • How do you define good sex?
  • What's your dirtiest fantasy?
  • Wildest sex story?
  • Boobs or booty?
  • What do you find to be the sexiest part of a man/woman/person's body?
  • Do you like it when a girl makes the first move?
  • What's on your sexual bucket list?
  • Lights on or off?
  • Favorite sex position ?
  • What's one of your go-to "moves"?
  • What's a sexy gift you'd love to receive?
  • What's on your ideal sexy playlist?
  • What's the hottest thing someone can say to you in bed?

The takeaway

Next date night plan? Play a round of 20-questions (or more!) cozied up on the couch and giving each other your full attention. You never know what you might learn about your man, even if you've been together for years—and staying curious about each other could be just the recipe you need for relationship satisfaction .

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Questions To Ask Your Boyfriend {The Ultimate List}

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Want some fun questions to ask your boyfriend ?

When it comes to relationships, there’s lots of things you need to know about your partner before a long term commitment. It’s important to know that you are not only physically and emotionally compatible, but also that your lives will mesh well together.

So asking relationship questions is important. Not only that, but asking questions can help you get to know each other on a deeper and more intimate level, and can help you spot any red flags early on.

text reads "questions to ask your boyfriend" with couple holding hands walking towards the beach.

One of the best ways to get to know your partner better is by asking questions. Fun questions, serious questions, random and personal questions…they’re all important.

It doesn’t matter if you just started dating or if you’ve been together for ages, asking some good questions can help you understand your boyfriend’s interests, goals, and values.

Plus, asking questions can help you express your own feelings and needs and help you both connect emotionally.

So, if you want to get the convo going, here are some questions that you may want to ask your boyfriend to get to know them better:

Basic questions to ask your Boyfriend:

  • What’s your favorite color?
  • What kind of music do you listen to?
  • What do you like to do in your spare time?
  • Are you an early riser or a late nighter?
  • Boxers or briefs?
  • Are you a cat or dog person?
  • What kind of movies/television shows do you like?
  • What do you like to eat?
  • Do you like to play games?
  • Do you have a favorite alcoholic drink?

Fun Questions to ask your Boyfriend:

Or try some of these funny couples questions …

  • If you were stranded on an island, what three things would you take with you?
  • What is the grossest thing you’ve ever eaten?
  • What was your most embarrassing moment?
  • Is there anything you love that other people think is gross?
  • What would you do if you were invisible for a day?
  • If you could fly, where would you fly to?
  • What would be your superpower of choice?
  • Have you ever been skinny dipping? Would you go?
  • What is your worst/grossest habit?
  • What would you do to survive a zombie apocalypse?

Childhood Questions to ask your Boyfriend:

  • Where did you grow up? 
  • What was your relationship like with your parents growing up?
  • Were you close with your grandparents?
  • Do you have any brothers or sisters?
  • Would you change anything about your childhood?
  • What’s your favorite childhood memory?
  • Who was your best friend as a child?
  • Do you and your family have any special traditions?
  • Are you close with your extended family?
  • What got you in the most trouble as a child?

Personal History Questions to ask your Boyfriend:

  • Where’s the coolest place you’ve ever been?
  • What’s your favorite thing you’ve ever done?
  • What accomplishment are you most proud of?
  • What were you like as a student?
  • What’s the scariest thing you’ve ever done?
  • Have you ever been in trouble with the law?
  • What’s the kindest thing you’ve ever done to someone?
  • What’s the meanest thing you’ve ever done to someone?
  • What’s the scariest thing that’s ever happened to you?
  • What’s your biggest regret?

Personality Questions to ask your Boyfriend:

  • What’s your best trait?
  • What’s your worst trait?
  • Do you have any bad habits I should know about?
  • What compliment do you get most from people?
  • If I spoke to your ex-girlfriend, what would she say about you?
  • Do you consider yourself an introvert or an extrovert?
  • How do you handle anger?
  • What’s something that makes you emotional?
  • If you’re sad or upset, what can I do to make you feel better?
  • Who do you turn to most when you need advice?

woman smiling at boyfriend asking questions.

Travel Questions to ask your Boyfriend?

  • Do you like to travel? Or would you prefer to stay home?
  • If you could travel anywhere in the world, where would you go?
  • What’s your favorite place you’ve ever been to?
  • What’s the most adventurous thing you’ve ever done?
  • Have you ever been anywhere really dangerous?
  • Are you good at navigating airports?
  • Are you afraid of flying?
  • What places are on your bucket list?
  • Would you rather stay in a lavish hotel or go camping?
  • How flexible are you with your travel plans?

Have You Ever Questions:

  • Have you ever been skydiving?
  • Have you ever done it on the beach?
  • Have you ever been in love?
  • Have you ever broken someone’s heart?
  • Have you ever dated two people at once?
  • Have you ever gone through a partner’s phone?
  • Have you ever been arrested?
  • Have you ever drove drunk?
  • Have you ever stolen something?
  • Have you ever been in a fist fight?

Serious questions to ask your Boyfriend: Do You Believe…

And check out our post for more deep questions to ask your boyfriend .

  • Do you believe in God?
  • Do you believe in religion?
  • Do you believe in ghosts?
  • Do you believe in aliens?
  • Do you believe in love at first sight?
  • Do you believe fairy tales can come true?
  • Do you believe that there are more good people in the world than bad?
  • Do you believe in miracles?
  • Do you believe that the world is round?
  • Do you believe in magic?

Past Relationship Questions

  • How many relationships have you been in?
  • Why did you break up?
  • Are you still friends with your ex’s?
  • How many people have you slept with?
  • How long have you and your ex been broken up?
  • Have you ever cheated on a partner?
  • What did you and your ex argue the most about?
  • If your ex had to say one bad thing about you, what would they say?
  • What would your ex say the best thing about you is?
  • Do other people consider you a player?

Flirty Questions to ask:

Try some of these flirty questions for your boyfriend …

  • Where do you see our relationship going?
  • Who’s relationship do you aspire to be like?
  • What do you think it takes to make a relationship work?
  • What do you think is the most important factor in a relationship?
  • How do you handle arguments in a relationship?
  • What is your love language?
  • What would you do if your friends and family didn’t approve of me?
  • What’s something you can improve on in your relationships?
  • What does monogamy look like to you?
  • What are your views on physical intimacy?

Questions to ask your BF about the Future:

  • Do you want to get married?
  • Do you want to have kids?
  • Where do you see yourself in 5 years?
  • Where do you want to live/settle down?
  • How do you see us splitting finances if we are to be together long-term?
  • What does your career look like in the future?
  • Would you be supportive of my career goals if we stayed together?
  • How involved would you be with my family?
  • What do you think the “role” of a wife is?
  • If we were ever struggling in our relationship, would you consider going to a counselor?

Questions about future Kids:

  • How many children do you want?
  • Would you prefer a boy or girl?
  • Do you have any names you like?
  • How do you see the roles divided between mom and dad?
  • If we had kids, would you stay at home or work?
  • Would you want me to stay at home or work?
  • How will we approach discipline with our children?
  • How would you respond if I couldn’t have children?
  • How do you feel about co-sleeping?
  • How would you handle it if our baby had a disability?

Dirty Questions To Ask Your Boyfriend:

  • What is the first thing that comes to mind when you think of me?
  • What’s the sexiest thing that someone has ever done for you?
  • What’s the wildest fantasy that you’ve ever had?
  • What’s the most flirty text or message you’ve ever sent?
  • What’s your favorite physical feature of mine?
  • What’s your favorite way to be touched or kissed?
  • What’s the most daring thing you’ve ever done in the name of love or lust?
  • What’s the hottest date that we’ve ever been on?
  • What’s the most intense physical sensation that you’ve ever experienced?
  • What’s your favorite part of our physical intimacy?
  • What’s the sexiest outfit you’ve ever seen me wear?
  • What’s your favorite part of foreplay?
  • What’s the most seductive thing that you’ve ever done to me?
  • What’s your favorite way to be teased or tempted?
  • What’s the most daring or adventurous place that you’ve ever been intimate?
  • What’s the most intense physical sensation that I’ve ever given you?
  • What’s the most flirtatious thing that we’ve ever done together?
  • What’s the sexiest thing that you’ve ever whispered in my ear?
  • What’s your favorite type of physical touch?
  • What’s the most sensual moment that we’ve ever shared together?

couple sitting on couch talking to each other.

Random Questions To Ask Your Boyfriend

  • If you had to choose one animal to be your loyal companion for the rest of your life, which one would you choose?
  • Would you rather explore space or the ocean depths?
  • If you could only eat one food for the rest of your life, what would it be?
  • If you were to describe yourself as a flavor, what would it be?
  • What’s the weirdest dream you’ve ever had?
  • If you could have any celebrity as your best friend, who would it be?
  • What’s the most spontaneous thing you’ve ever done?
  • If you could be any fictional character’s sidekick, who would you choose?
  • What’s the most impressive thing that you’ve ever built or created?

Things To Ask Your Boyfriend

  • If you could live in any fictional universe, which one would you choose?
  • What’s the most unique skill or talent that you possess?
  • If you had to live in a different country for a year, which one would you choose?
  • If you could only listen to one album for the rest of your life, which one would it be?
  • What’s the most memorable gift that you’ve ever given someone?
  • If you could witness any event from history, what would it be?
  • What’s the most unusual job or career that you’ve ever had?
  • If you could have any object from a movie or TV show, which one would you choose?
  • What’s the most creative Halloween costume you’ve ever worn?
  • If you could go on a road trip with any fictional character, who would it be and where would you go?
  • What’s the most interesting fact or piece of trivia that you know?

Cute Questions To Ask Your Boyfriend

  • What’s your favorite thing about me?
  • What’s the most romantic thing that you’ve ever done?
  • What’s your favorite thing to do together?
  • What’s your idea of the perfect date?
  • What’s your favorite memory of us together?
  • What’s the sweetest thing that someone has ever done for you?
  • What’s the most thoughtful gift that you’ve ever given someone?
  • If you could travel anywhere in the world with me, where would you want to go?
  • What’s your favorite thing about cuddling?
  • If you could relive one moment from our relationship, which one would it be?
  • What’s your favorite nickname for me?
  • What’s the most important thing in a relationship to you?
  • What’s something that you’ve always wanted to do with me?
  • What’s your favorite thing about us as a couple?
  • What’s your favorite thing that we have in common?
  • What’s the most important lesson that you’ve learned from our relationship?
  • What’s something that you’ve always wanted to tell me?
  • What’s your favorite thing about our conversations?
  • What’s the most valuable thing that you’ve learned about love from our relationship?
  • What’s your favorite thing about waking up next to me in the morning?

Important Questions To Ask Your Boyfriend

  • What are your long-term goals and aspirations?
  • What do you value most in a relationship?
  • How do you handle conflict in a relationship?
  • What are your top love languages, and how do you like to receive love?
  • How important is honesty and transparency to you in a relationship?
  • What are your expectations for communication in our relationship?
  • How do you envision your future with me?
  • What are your thoughts on marriage and family?
  • What do you think is the biggest challenge in our relationship?
  • How do you balance personal time and time spent together in a relationship?
  • How do you handle stress and difficult times?
  • What are your thoughts on finances and how they should be managed in a relationship?
  • What is your approach to personal growth and self-improvement?
  • How do you feel about vulnerability and sharing personal experiences?
  • What are your thoughts on forgiveness and second chances in a relationship?
  • What do you think is the most important quality in a partner?
  • How do you like to show appreciation and gratitude in a relationship?
  • What are your thoughts on boundaries and how they should be established in a relationship?
  • What role do you think physical intimacy plays in a relationship?
  • What do you think is the key to a successful, long-lasting relationship?

This or That Questions For Boyfriend

  • Public displays of affection or private affection?
  • Movie night at home or a night out at the cinema?
  • Cook together or order takeout?
  • Surprises or planned events?
  • Share personal stories or keep things private?
  • Texting or phone calls?
  • Meeting the family or spending time with friends?
  • Cuddling on the couch or going for a walk together?
  • Being spontaneous or planning everything out?
  • Talking things out or giving each other space to cool off?
  • One big vacation or multiple small getaways throughout the year?
  • Candlelit dinner at home or a fancy restaurant?
  • Celebrating every milestone or just the big ones?
  • Watching sports together or watching a romantic movie?
  • Gifts or thoughtful gestures?
  • Talking about the future or living in the moment?
  • Saying “I love you” often or letting actions speak louder than words?
  • Spending weekends together or having some alone time?
  • Sharing responsibilities or dividing them equally?
  • Personal hobbies or shared interests?

couple holding hands, facing each other and laughing outside.

Questions To Ask Your Boyfriend About Yourself

  • What was your first impression of me when we first met?
  • What do you think are my best qualities?
  • What are some areas you think I can improve in?
  • How do you think I’ve changed since we first started dating?
  • What are some things that make me happy?
  • What are some of my favorite hobbies or interests?
  • What are some of my biggest fears or insecurities?
  • What are some of my goals or dreams for the future?
  • What do you think is my love language?
  • What are some of the things that we have in common?
  • What do you think is my favorite memory with you?
  • What do you think is my favorite food or restaurant?
  • What do you think is my biggest pet peeve?
  • What do you think is my favorite type of music?
  • What are some of the things you admire about me?
  • What is something that you have learned about me that you didn’t know before?
  • What is something that I do that always makes you smile?
  • What do you think is my biggest accomplishment so far?
  • What are some of my future aspirations that you know of?
  • What do you think is my favorite way to unwind after a long day?
  • What do you think is my favorite thing to do on the weekends?
  • What do you think is my favorite type of weather?
  • What is something that I have done that has impressed you?
  • What is something that you love about my personality?
  • What is something that you find unique or interesting about me?
  • What do you think is my biggest strength in our relationship?
  • What is something that you think I should be more confident about?
  • What is something that you appreciate about the way I communicate with you?
  • What do you think is my favorite thing to do with you?
  • What do you think is something that I could teach you?

Yes or No Questions To Ask Your Boyfriend

  • Have you ever been in love before?
  • Do you like trying new things?
  • Do you enjoy spending time outdoors?
  • Do you prefer staying in for dates?
  • Do you believe in soulmates?
  • Are you close with your family?
  • Do you have any pets?
  • Do you like to travel?
  • Are you a morning person?
  • Do you enjoy watching movies?
  • Do you like to cook?
  • Are you religious?
  • Do you have any hobbies?
  • Do you think you are a spontaneous person?
  • Do you value honesty and transparency in a relationship?
  • Do you enjoy spending time with me?
  • Have you ever cheated on me?
  • Do you see a future with me?
  • Are you happy in our relationship?
  • Have you ever lied to me about something important?
  • Do you trust me?
  • Do you find me physically attractive?
  • Have you ever had feelings for someone else while we were together?
  • Do you think we communicate well?
  • Are you comfortable being yourself around me?
  • Do you think we share the same values?
  • Do you believe in marriage?
  • Do you want children in the future?
  • Do you think we have enough intimacy in our relationship?
  • Do you believe in fate or destiny?

Juicy Questions To Ask Your Boyfriend

  • What’s your favorite body part on me?
  • What’s your favorite body part on you?
  • What is one thing you wish we would do more of?
  • What is something you’d like to try with me?
  • How do you see our relationship going in the next year?
  • Do you think we are “meant to be”?
  • What is one secret you have never told anyone else?
  • Have you ever shared a secret about me to anyone?
  • What is one thing you would change about me?
  • What is one thing you would change about yourself?
  • If you could ask me not to speak to one of my friends ever again, who would it be?
  • What’s one fantasy you’ve done?
  • Do you think you know me better than I know you? Or vice versa?
  • Which of us would you say is “settling” for the other?
  • Which one of us do you think is dating “out of their league”?
  • Have you ever thought about breaking up with me?
  • Were you ever scared I would break up with you?
  • What is one thing you’ve always wanted to say to me, but have been to afraid to?
  • Do you think we will end up together forever?
  • Tell me a secret about us.

couple looking at computer reading questions for boyfriend.

Loving Questions For Your Boyfriend

  • What do you love most about me?
  • How did you know you were in love with me?
  • What’s the most thoughtful thing you’ve ever done for me?
  • What makes you feel loved and appreciated in a relationship?
  • What do you think is the key to a successful and happy relationship?
  • Do you see us growing old together?
  • What’s your idea of the perfect date with me?
  • What’s the most romantic thing you’ve ever done or said to me?
  • How has our relationship changed you for the better?
  • What’s your favorite physical feature about me?
  • What’s the sweetest thing I’ve ever done for you?
  • How do you express your love and affection for me?
  • Do you feel that we are each other’s soulmates?
  • How can I make you feel more loved and appreciated in our relationship?
  • What’s one thing you would like us to do together that we haven’t done yet?
  • What do you appreciate most about our relationship?
  • What’s your favorite thing to do with me?
  • How have you grown as a person since we started dating?
  • What’s your favorite quality about me?
  • What’s one thing you’re looking forward to in our future together?
  • What’s the best piece of advice you’ve received about relationships?
  • What’s something you’ve learned from our relationship?
  • What’s something you’d like to do more of as a couple?
  • How do you see our relationship evolving in the future?
  • What’s your favorite non-physical attribute about me?
  • What’s one thing you appreciate about our communication as a couple?
  • What do you think sets us apart from other couples?
  • What’s something you admire about me?
  • What’s one thing you appreciate about the way we support each other in our relationship?

Truths To Ask Your Boyfriend

  • What are your greatest fears?
  • What’s your biggest regret in life so far?
  • What’s your biggest accomplishment in life so far?
  • What motivates and drives you in life?
  • What’s your proudest moment in life?
  • What’s the most important lesson you’ve learned in life?
  • What’s something you wish you could change about yourself?
  • What’s your definition of success?
  • What’s something that always makes you happy?
  • What’s something that always makes you sad?
  • What’s your favorite childhood memory?
  • What’s your biggest pet peeve?
  • What’s your biggest turn-off in a relationship?
  • What’s your favorite thing about yourself?
  • What’s something you’re passionate about?
  • What’s the biggest challenge you’ve faced in life so far?
  • What’s your biggest goal in life?
  • What’s something you’re afraid to tell me?
  • What’s the most meaningful thing someone has ever done for you?
  • What’s something you’d like to achieve in the next year?

Would You Rather Questions For Your Boyfriend

  • Would you rather live in the city or the countryside?
  • Would you rather travel to the beach or the mountains?
  • Would you rather spend a day at the amusement park or the zoo?
  • Would you rather watch a movie at home or go out to the cinema?
  • Would you rather have a night in or a night out with friends?
  • Would you rather have a small intimate wedding or a big extravagant one?
  • Would you rather go on a road trip or a cruise?
  • Would you rather have a pet dog or a pet cat?
  • Would you rather spend the day hiking or at the beach?
  • Would you rather stay in a luxurious hotel or go camping?
  • Would you rather go on a romantic dinner date or cook at home together?
  • Would you rather spend the day exploring a new city or relaxing at home?
  • Would you rather have a staycation or a vacation abroad?
  • Would you rather have a night in with Netflix or go out dancing?
  • Would you rather have a night of passion or a slow, intimate evening?
  • Would you rather be able to fly or be invisible?
  • Would you rather be rich and unhappy or poor and happy?
  • Would you rather be able to read minds or teleport?
  • Would you rather have a rewind button in your life or a pause button?
  • Would you rather live in the past or the future?
  • Would you rather have the power to heal or the power to time travel?
  • Would you rather be stuck on an island alone or with someone you dislike?
  • Would you rather have unlimited money or unlimited time?
  • Would you rather be famous or wealthy?
  • Would you rather live without music or television?
  • Would you rather have a personal chef or a personal trainer?
  • Would you rather have a photographic memory or the ability to forget anything you want?
  • Would you rather go back to school or start a new career?
  • Would you rather live forever or be able to bring someone back from the dead?
  • Would you rather have a billion dollars or true love?

Use these questions as a starting reference to get to know your boyfriend better. The idea here is to connect on a deeper level, while at the same time looking for any red flags or suggestions that your lifestyles might not mesh together well. 

travel questions to ask your boyfriend

Sara, a seasoned expert in wedding planning and date ideas, brings a wealth of experience to our couples blog. With a background in the television industry and hands-on involvement in a dozen weddings, including working as a wedding assistant on "My Fair Wedding with David Tutera," Sara has an innate understanding of the magic that makes weddings truly special. Growing up with four sisters has given her unique insights into the dating world, making her a go-to source for practical and heartfelt dating advice. Her knowledge and enthusiasm make her the perfect guide for couples seeking to infuse their relationships with creativity and love.

Couple Travel The World

200+ Questions to Ask Your Boyfriend – Over Text or In Person!

By: Author coupletraveltheworld

Posted on Last updated: May 16, 2022

Categories Conversation Starters

Looking for Questions to Ask Your Boyfriend? Good news – you have come to the right place!

Whether you are in a new relationship or you’ve been with your significant other for a long time, communication is essential. For new relationships, communication is how you get to know each other. Keeping up communication will help strengthen the connection between couples who have been together for a while.

Maybe you’re starting a new relationship, or perhaps you and your boyfriend have been together for so long it seems that you don’t have anything to talk about at times. Or, your beau may be a little shy, and you’re having trouble getting him to open up. No matter your relationship situation, these questions are sure to get your man talking.

In this article, you will find over 200 questions to ask your boyfriend . These questions range from deep and thought-provoking to fun and flirty to plain random and silly. Whether your guy is outgoing, shy, or somewhere in between, these questions will help you learn a lot about him and possibly strike up some interesting discussions.

You don’t have to ask him every single question in this article. This is just a broad range of questions to get the conversation flowing. Depending on how long you’ve dated, you may want to start with some of the flirty, fun, or exciting questions and build up to the romantic and deep ones.

Deep Questions to Ask Your Boyfriend

These questions are great if you want to dig deep and really get to know your boyfriend or get him to open up. If your relationship is new, you may not want to ask any of these questions first. Remember to keep an open mind when he answers and let the conversation flow naturally.

What song makes you cry?

What is your favorite childhood memory?

Are you sentimental?

What is one thing you’ve always wanted to do but never got the chance?

What is your biggest insecurity?

What is your biggest fear?

What is your biggest regret?

What is the best advice that you have ever been given?

What is a bad habit that you have had in the past but have overcome?

How often do you change your view of the world?

What three events do you think have had the most significant impact on your life and shaped you into who you are today?

What is the last movie that made you cry?

Have you ever done a random act of kindness? If so, what was it?

What is one small thing that people can do daily that will significantly improve their life?

When you were growing up, who was your role model?

What is one thing that people misunderstand about you?

When was one time that you stepped out of your comfort zone?

What is the most important lesson that you have learned?

How important is religion or spirituality to you?

Can money buy happiness?

What tradition did your family practice when you were growing up that you would like to continue if you have children?

What is one piece of advice you would give your younger self?

If you could fix one problem in the world, what would it be?

If you had to live without one of your senses, which one would you choose to live without and why?

Are you more motivated by praise or criticism?

What is the biggest fear that you have overcome?

Do you believe there is a difference between living life and just existing?

Would you want to be well-known in life but forgotten in death, or unknown in life but remembered forever after death?

What is one thing you would like to accomplish before you die?

Who do you think would come to your funeral?

 What was a nickname you had when you were younger that you hated but your parents loved?

Have you ever had a near-death experience?

Do you believe what goes around comes around?

What is the best way to earn someone’s respect?

Do you follow your heart or your brain when making important decisions?

See more: This or That Questions for Couples

travel questions to ask your boyfriend

Fun Conversation Starters for Beau

These questions are meant to be precisely what the title implies: fun but not necessity dirty questions. Not only will they give you a glimpse of his sense of humor and what he finds funny, but he will find out what you find funny by the type of questions you ask.

What is the most embarrassing thing you’ve ever done or that has ever happened to you?

What is the most spontaneous thing you’ve ever done?

Who is your favorite comedian?

What is the stupidest thing you have ever done?

What is your go-to karaoke song?

What is the most ridiculous thing you have ever seen?

What is the dumbest trend that is popular right now?

What is the funniest catchphrase you have ever heard?

What is one thing that makes you burst out laughing?

Is there any word that makes you laugh every time you hear it?

What is the funniest movie you’ve ever seen?

What is the weirdest smell you have ever smelled?

What is the best Wi-fi name you have seen?

What is the most ridiculous fact that you know?

What is something that you think everyone looks stupid doing?

What is the funniest joke that you have memorized?

What is the weirdest thing you have seen at someone else’s home?

What is an odd question that you have always wanted to ask me?

What is a movie or TV show that you really like and are embarrassed to tell anyone?

Who can you do a voice impression of?

What is the funniest name you have ever heard?

What is the creepiest thing you could say to a stranger?

Where is the most inappropriate place you have ever passed gas?

What is the best prank you can play on someone?

What is the funniest or most ridiculous tattoo that you have ever seen?

What is the weirdest thing you have seen while you were driving?

What is the most annoying commercial?

What is the funniest or weirdest inside joke you’ve ever been a part of?

Have you ever peed in a pool?

Has anyone ever walked in on you while you were in the bathroom, or have you ever walked in on anyone in the bathroom?

What is the scariest movie you have ever seen?

What is the weirdest conversation that you’ve ever overheard?

Do you have any odd family members?

  • See more: First Date Questions

quizzes for couples

Questions to Ask When You’re Bored

Are there long uncomfortable silences when you and your boyfriend are on the phone? Or maybe you have found that you don’t have much to talk about at dinner.

These questions are great ice breakers and conversation starters. Some of them are random, some are just plain silly, but they all are guaranteed to get the conversation flowing and hopefully get a few laughs out of both of you.

What would you do if you caught me sleepwalking?

Do you prefer the cold or warm side of the pillow?

Would you rather be invisible or have X-ray vision?

If you could be invisible for a day, what would you do?

What superpower do you wish you had?

Is a hotdog a sandwich?

Does pineapple belong on pizza?

What movie do you like to watch over and over?

What is your dream road trip destination?

What would you rename yourself if you could change your name?

Would you rather leave your hometown and not be able to come back, or stay in your hometown but not be able to escape?

Which celebrity would make the worst leader of a country?

If you built a treehouse, what would it look like, and what would be in it?

What could you give a thirty-minute impromptu speech on?

What celebrity would be the worst dinner guest?

What topic do you know WAY too much about?

What is your favorite card or board game?

What is your least favorite card or board game?

What celebrity do you think is a massive jerk in real life?

Do you collect anything?

Who is famous for their talent, but they really shouldn’t be?

How old would you be if you had to be one age forever?

What is your favorite season?

What is your favorite holiday?

If you could learn any language, what language would it be?

Which food do you go for first at Thanksgiving dinner?

What movie title currently describes your life?

What was your favorite class in school?

What was your least favorite class in school?

If you had a time machine, would you go back in time, or would you travel to the future?

Do fish have necks?

travel questions to ask your boyfriend

Romantic Questions to Ask Your Boyfriend

These questions are ideal for getting to know more about your partner on a more romantic level, without turning the heat up too much. If you don’t know much about your boyfriend’s romantic side yet, these will surely help.

What is your idea of a perfect date?

Do you know your love language?

What is your favorite thing we do together?

Do you think we would have dated in high school?

What is your favorite restaurant that we eat at together?

What is a romantic honeymoon destination?

What do you remember most about the first time we met?

What is your favorite love song?

What would be your perfect romantic date night?

What is your favorite romantic movie?

Which connection is more important in a relationship, an emotional or physical one?

What relationship do you admire from your friends and family the most?

Have you ever kissed someone under the mistletoe?

What is something that you didn’t want me to know about you when we first started dating?

What is your favorite memory of us?

What is your favorite way to show affection?

What is your favorite way to receive affection?

What is one thing about our relationship that makes it unique from other people’s relationships?

If we could take a trip together anywhere right now, where would you want to go?

Which one of us is more affectionate?

What song makes you think about me?

Do you like grand romantic gestures or smaller ones?

What is one difference between us that you love?

What is one similarity between us that you love?

What advice would you give someone about long-distance relationships?

After having a bad day, would you prefer a nice dinner out or a cozy movie night?

What is an item on your bucket list that you would like us to accomplish together?

What is one thing about yourself that you’ve never told me before?

If there was one cookie left, would you give it to me?

Has being in a relationship with me helped you learn more about yourself?

Questions to Ask Over Text

Even if you’re not talking in person or over the phone, you can still ask questions! These are especially good if you haven’t been seeing each other very long, but they work for long-term couples as well. Some of these questions can also be asked in person, but many make more sense when asked via text.

What is your favorite meme or gif?

Does double texting bother you, or is it no big deal?

Do you prefer the beach or the snow?

Would you rather live in another country or outer space?

What’s your favorite place to get carry-out or delivery from?

What app do you use the most?

What is the one app that I might not have that you think I should get?

What is the best picture you have ever taken on your phone?

What is the worst text that you accidentally sent?

What is the funniest picture you have on your phone?

What is the most ridiculous thing you have seen online?

What is your biggest pet peeve on social media?

Are you an early bird or a night owl?

If you were a color, what color what you be?

What food are you craving right now?

What song always puts you in a good mood?

How many phones have you broken or lost?

What is your phone or computer wallpaper?

What is your favorite podcast?

Would you rather be hot or cold?

Which do you prefer: roller coasters or Ferris wheels?

What is your favorite emoji?

What is your favorite ice cream flavor?

Do you believe in aliens?

What is your favorite animal?

If you could be any animal, what would you be?

If you were a dog, what kind of dog would you be?

If you could only listen to one song for the rest of your life, what song would it be?

If you were forced to choose only one food and one drink to have for the rest of your life, what would they be?

Would you rather spend a week in New York City or Los Angeles?

Would you rather have 24 hours of sunlight or 24 hours of moonlight?

What television show could you binge-watch all day?

If you could cancel one television show, what would it be?

Are you an introvert or an extrovert?

If you could, would you quit your job and travel the world?

See also: Get to know you questions

Interesting Questions to Ask

This is a combination of different types of questions. Some are funny, freaky some are random, and some are thought-provoking. But they are all interesting, and not only will they tell you more about him, but they will also show him how interesting you are as well!

Most of these are open-ended, and the answers require some explanation, so ask away and get ready for the conversation to take off.

What is your biggest pet peeve?

If you could have dinner with any famous person, living or dead, who would it be?

What is the weirdest thing that you have in your closet?

What activity or thing calms you the most?

What seemed normal in your family growing up but seems weird now?

If animals could talk, which animal would be the rudest?

If you could be a part of any TV family, which family would it be?

Who would you pick to play you in a movie?

What is your ideal weekend?

What was your favorite TV show when you were a child or teenager?

What would you take if you could only take five movies to a deserted island?

What is the worst job you have ever had?

What is the worst date you have ever been on?

Did you ever go to summer camp?

If you were accidentally put in an insane asylum, how would you convince them that you weren’t actually crazy?

What fictional character is excellent in the book, movie, or television show they’re in but would be impossible to deal with in real life?

What is the most exciting piece of trivia or useless fact that you know?

What historical figure do you think is not as impressive as most people think they were?

What is the worst purchase that you have ever made?

What would be on your perfect burger?

Who is your favorite villain?

What is one thing you like to do that is traditionally considered feminine?

What is something peculiar that you used to eat when you were a child?

Aside from people and animals, what is one thing you would grab out of your house if it were on fire?

What is a weird flavor combination that you like?

What is a random compliment you have received that you have never forgotten?

Have you ever had a paranormal experience?

What movie would be better if the plot were reversed?

What was fun to do one time, but you don’t think that you’ll ever do again?

What is the worst injury you have ever gotten?

If you go to a restaurant and the service is terrible, is it okay not to leave a tip?

If you could prevent one historic disaster, which one would it be?

What is your worst travel trait?

What would be inscribed on your tombstone?

How do you avoid procrastination?

Flirty Questions to Ask Your Boyfriend

If you’re feeling flirty or want to ask him some fun cute questions without getting too deep or romantic, these questions are perfect. Plus, some of these questions may be excellent icebreaker questions to lead up to the more romantic ones.

What is the best pickup line you’ve ever heard?

What is the worst pickup line you’ve ever heard?

How old were you when you had your first kiss?

Do you check out your reflection?

Who is your celebrity crush?

What was your first impression of me?

What couples costume have you always wanted to do for Halloween?

Do you smile when you receive a text message from me?

Would you rather hug for five seconds or kiss for one second?

What is the craziest thing you have ever done to impress someone?

Which do you like better: movie dates or restaurant dates?

Do you enjoy staying in or going out?

Do you think that men should always make the first move, or is it okay for women to make the first move?

Have you ever randomly kissed someone in the middle of a conversation?

What did you think when you first saw or met me?

Are you ticklish?

Would you rather be married to a 10 with a horrible personality or a 6 with a fantastic personality?

Do you ever still get nervous around me?

What do you think is your most attractive non-physical feature?

What is my most attractive non-physical feature?

Would you rather be called sexy or intelligent?

Would you rather never be able to kiss or never be able to cuddle?

Would you ever write a song or a poem for me?

Do you like pet names, or do you think they’re silly?

Are you a good dancer?

Would you ever lay on the grass and watch the stars with me?

couple-travel-quotes

I hope this list of more than 200 questions will be helpful the next time you’re bored, feeling flirty, or feel like you’ve run out of things to talk about with your boyfriend. Good luck!

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288 Fun and Romantic Questions to Ask Your Boyfriend

Discover a list of 200+ fun, romantic, and juicy questions designed to deepen your connection with your boyfriend. Perfect for date nights or cozy chats, these questions will add a spark to your LDR conversations!

Woman Asking Questions To Her Boyfriend

In any relationship, especially long-distance ones, good communication is key to building a strong bond. It’s important to ask your boyfriend meaningful questions, no matter how long you’ve been together. These questions help you learn more about him and strengthen your trust and connection. When you talk openly and listen to each other, it helps you grow together. It’s better to understand each other deeply than to guess what the other is feeling. In a long-distance relationship, this is even more crucial. Creating a safe space for sharing feelings openly, without judgment, shows that you care and are invested in the relationship. This builds a deeper, more loving partnership.

Below are categorized lists of questions that will help you deepen your connection with your boyfriend. They range from getting to know him better to fun and flirty inquiries about each other and your relationship, and even some playful and romantic questions designed to make him laugh. For the adventurous, there’s also a set of juicy (NSFW) questions!

100 Important questions to ask your boyfriend to know him better

In a long-distance relationship, it can feel like you know everything about your partner, from their favorite movie to what they like on their hamburger. But there’s always more to discover, especially when you can’t be together physically.

To deepen your connection and learn more about your boyfriend’s life, thoughts, and values, we’ve put together a list of personal questions. These questions are designed to reveal more than just one-word answers. They’ll help you uncover funny stories, hidden facets of his personality, and the reasons behind his likes and dislikes.

Perfect for keeping the conversation lively and engaging, no matter the distance!

  • If you could live in any historical era, which would you choose and why?
  • What book has had the most significant impact on your life?
  • Do you believe in fate or that we create our own destinies?
  • What’s one thing you would change about your childhood?
  • What does your ideal weekend look like?
  • If you could have dinner with any three people, dead or alive, who would they be?
  • What are you most grateful for in your life?
  • What’s one dream you have yet to accomplish?
  • Do you believe in ghosts or other supernatural entities?
  • What’s the most challenging decision you’ve ever made?
  • What’s your favorite family tradition?
  • What’s the best piece of advice you’ve ever received?
  • What’s your favorite thing about yourself?
  • What’s one thing you’ve never told anyone?
  • What does your perfect day look like from morning to night?
  • What’s one thing you’re scared to ask me but really want to know the answer to?
  • What’s your biggest regret in life?
  • What’s your favorite childhood memory?
  • If you could change one thing about the world, what would it be?
  • What’s the most significant risk you’ve ever taken?
  • What’s the most adventurous thing you’ve ever done?
  • What’s one subject you wish you knew more about?
  • If you could have any job in the world, what would it be?
  • What’s something that overwhelms you?
  • What’s your favorite way to relax after a stressful day?
  • What are three things on your bucket list?
  • Do you believe in soulmates?
  • What’s your most treasured possession?
  • What’s the biggest lesson you’ve learned in life?
  • What’s your favorite quote or saying?
  • How do you handle conflict in a relationship?
  • What’s your favorite thing about our relationship?
  • What’s something you’d like to learn how to do?
  • What’s the most meaningful gift you’ve ever received?
  • What’s something you’re looking forward to in the future?
  • What’s your favorite way to spend time outdoors?
  • If you could relive one day of your life, which would it be?
  • What’s the most important thing in a friendship?
  • How do you like to celebrate your birthday?
  • What’s something you find really romantic?
  • What’s your favorite movie and why?
  • What’s your biggest fear?
  • What’s one thing you wish you were better at?
  • How do you like to be comforted when you’re upset?
  • What’s the most interesting place you’ve ever visited?
  • What makes you feel most alive?
  • What’s something you’ve always wanted to try but haven’t yet?
  • What’s your favorite family story?
  • What’s something you’re proud of?
  • What’s your favorite holiday and why?
  • What’s the best compliment you’ve ever received?
  • What’s your favorite type of cuisine?
  • What’s something you do to relax?
  • What’s the most spontaneous thing you’ve ever done?
  • If you could have any superpower, what would it be?
  • What’s your favorite song to dance to?
  • What’s one habit you’d like to break?
  • What’s something that always makes you smile?
  • What’s the best part of your day?
  • What’s your favorite thing to do on a rainy day?
  • What’s the best vacation you’ve ever had?
  • What’s your favorite animal and why?
  • What’s one thing you’d like to be remembered for?
  • What’s your favorite type of weather?
  • What’s your biggest pet peeve in relationships?
  • What’s something you’ve learned about yourself this year?
  • What’s your favorite sport to watch or play?
  • What’s the best concert you’ve ever been to?
  • What’s one thing you can’t live without?
  • What’s the most unusual thing you’ve ever eaten?
  • What’s your favorite thing to cook or bake?
  • What’s your favorite piece of art?
  • What’s something that always calms you down?
  • What’s your favorite memory of us together?
  • What’s one thing you’d like to change about yourself?
  • What’s your favorite form of self-care?
  • What’s the best part of your job?
  • What’s your favorite board game or card game?
  • What’s something you’re glad you tried but wouldn’t do again?
  • What’s one thing you’d like to learn about me?
  • What’s your favorite type of music?
  • What’s the best gift you’ve ever given?
  • What’s something you used to believe but don’t anymore?
  • What’s your favorite way to exercise?
  • What’s something you miss about being a kid?
  • What’s the most important thing you learned from your parents?
  • What’s one thing you’d like to achieve in the next five years?
  • What’s your favorite thing to do when you’re alone?
  • What’s the kindest thing someone has ever done for you?
  • What’s one thing that helps you manage stress?
  • What’s the most challenging part of your daily routine?
  • What’s your favorite memory from your teenage years?
  • What’s something you’re not good at but enjoy doing?
  • What’s your idea of a perfect date?
  • What’s the most valuable thing you’ve learned in a relationship?
  • What’s your favorite thing about your hometown?
  • What’s one thing that always makes you laugh?
  • What’s something you’d like to do together that we haven’t yet?
  • What’s the best advice you could give someone?
  • What’s something you’re excited to do in the next year?

50 Fun Questions To Ask Your Boyfriend About Yourself

Even though your boyfriend might be open about his feelings, there are probably some things you haven’t talked about yet. These 50 questions can help you learn about his first impressions, special memories, and moments he hasn’t shared with you before.

  • What’s a habit of mine that you find adorable?
  • If you could describe our relationship in three words, what would they be?
  • What song always reminds you of me?
  • What’s the silliest argument we’ve ever had, and why was it funny?
  • If we were a TV couple, who would we be and why?
  • What’s one thing I do that always makes you laugh?
  • What adventure would you love to take me on?
  • What’s something I’m really good at that you admire?
  • If you could give me a superpower, what would it be and why?
  • What’s your favorite thing I’ve ever said to you?
  • If I were an animal, which one would I be and why?
  • What’s the most surprising thing you’ve learned about me?
  • What’s a dream you’ve had about me that you remember?
  • How do you think I’ve changed since we first met?
  • What’s your favorite thing to do together on a lazy day?
  • If I were a dish, what would I be and why?
  • What’s something I’m surprisingly good at?
  • How would you describe my sense of humor?
  • What’s a movie character that reminds you of me?
  • What’s your favorite outfit of mine?
  • What’s a talent of mine that you think is underappreciated?
  • What’s the kindest thing I’ve ever done for you?
  • What’s something I worry about that you find endearing?
  • If our love story was a book, what would the title be?
  • What’s the most meaningful compliment you’ve ever received from me?
  • If I were a color, which one would I be and why?
  • What’s your favorite photo of us and what’s the story behind it?
  • What’s the best way I support you when you’re feeling down?
  • What’s a small thing I do that has a big impact on you?
  • If we could travel anywhere together, where would you want us to go?
  • What’s a subject you think I know a lot about?
  • How do you think I’ve influenced your life for the better?
  • What’s the funniest thing we’ve experienced together?
  • What’s a small thing I do that you think is incredibly cute?
  • How would you describe my personality to someone who’s never met me?
  • What’s something I’m passionate about that you admire?
  • If you could relive any day we’ve spent together, which would it be?
  • What’s your favorite thing about our conversations?
  • What’s a scent or perfume I wear that you love?
  • What’s the most thoughtful thing I’ve ever said to you?
  • If I were a dessert, what would I be and why?
  • What’s a hobby or interest of mine that you want to learn more about?
  • How do you think I’ve made you a better person?
  • What’s the most unexpected thing you’ve learned from me?
  • What’s a book or movie I love that you also enjoyed because of me?
  • What’s a dream or goal of mine that you fully support?
  • What’s something I do when I’m excited that you find adorable?
  • If you could pick one thing of mine to keep forever, what would it be?
  • What’s a trait of mine that you think is unique to me?
  • How do you think we’ve grown as a couple since we first started dating?

49 Deep Questions To Ask Your Boyfriend About Your Relationship

Asking your boyfriend deep questions about your relationship can really help you both. It opens up new ways to talk about your feelings. You’ll find out what he enjoys in the relationship and learn how you both can improve your communication and openness with each other.

  • If our love story was a book, what genre would it be?
  • What fictional couple do you think we’re most like?
  • If you could plan the perfect date for us, what would it involve?
  • What’s one word that you think captures the essence of our relationship?
  • What was the first thing about me that caught your attention?
  • What’s one thing about our relationship that took you by surprise?
  • If we were a TV show, what would be our theme song?
  • What’s the funniest memory you have of us together?
  • If we could go on a dream vacation, where would we go and why?
  • What’s a new hobby you’d like us to try together?
  • What’s your favorite photo of us, and why?
  • If we were superheroes, what powers would we have?
  • What’s the most valuable lesson you’ve learned from our relationship?
  • If you could choose one memory of us to keep forever, which one would it be?
  • What’s one thing you hope never changes about us?
  • What do you think is the most unique aspect of our relationship?
  • If we made a time capsule to be opened in 10 years, what would you put in it?
  • What’s something small I do that makes you smile every time?
  • If we were to start a business together, what would it be?
  • What’s one adventure you’re looking forward to having with me?
  • What’s a challenge we’ve overcome together that made us stronger?
  • If you could dedicate a song to our relationship, which one would it be?
  • What’s the best piece of advice you’ve received about relationships that you think applies to us?
  • What’s something you were surprised to learn about me?
  • What’s one dream you have for our future together?
  • How do you think we’ve grown as a couple?
  • What’s the silliest thing we’ve ever argued about?
  • What’s something I do that always makes you laugh?
  • If our relationship was a dance, what kind would it be?
  • What’s a tradition we’ve started that you love?
  • What’s something you always wanted to tell me but haven’t yet?
  • What’s the most romantic thing you think we’ve done together?
  • What’s one thing we haven’t done together yet that you’re excited to try?
  • If we were a flavor, what would we be?
  • What’s your favorite thing to cook or eat together?
  • What’s a skill or talent of mine that you admire?
  • What’s the best surprise you’ve ever received from me?
  • What’s one thing you think makes our relationship unique from others?
  • If we were animals, what kind would we be?
  • What’s the best advice I’ve ever given you?
  • What’s your favorite thing about our daily routine?
  • If we could relive any year of our relationship, which would it be and why?
  • What’s something about me that you think complements something about you?
  • What’s one thing you’re glad we agree on?
  • What’s the most meaningful gift you’ve ever received from me?
  • If we could have a celebrity couple join us for dinner, who would you pick and why?
  • What’s one thing about our future together that excites you the most?

29 Flirty questions to ask your boyfriend

In any stage of a relationship, flirting adds a spark of excitement! It’s all about playful and enjoyable interactions.

The best flirty questions are light-hearted, a bit whimsical, and encourage creativity. Aim for questions that are fun and not too serious or inappropriate. A touch of suggestive humor is great, but remember, it’s all about striking the right balance!

Want something with a bit more zing? Don’t worry, we’ve got some juicy questions coming up too!

  • If you could describe my scent in three words, what would they be?
  • What’s a fantasy you’ve always had but never told me about?
  • What’s one thing I do that drives you absolutely crazy (in a good way)?
  • If we were in a movie, which celebrity couple would we be like?
  • What’s your favorite memory of us together?
  • If you could pick any place in the world for us to make love, where would it be?
  • What’s a song that always makes you think of me?
  • How do you like to be seduced?
  • What’s your favorite thing to do together on a rainy day?
  • If we were stranded on a deserted island, what’s the one thing you’d want to have with us (besides essentials)?
  • What’s something naughty you’ve always wanted to try with me?
  • How do you feel when you see me in your shirt?
  • If I was a dessert, what would I be and why?
  • What’s the most romantic thing you’ve ever wanted to do for me?
  • Which of my outfits do you find irresistible?
  • What’s one thing I do that makes you feel desired?
  • How do you feel about role-playing in the bedroom?
  • What’s your favorite way to receive affection?
  • If you could choose any movie scene to recreate with me, which would it be?
  • What’s a romantic dream you’ve had about us?
  • If we wrote a love story about us, what would the title be?
  • How do you feel about spontaneous displays of affection?
  • What’s something I do that makes you feel butterflies?
  • If we had 24 hours to do anything we wanted, no limits, what would we do?
  • What’s a habit of mine that you find incredibly sexy?
  • What’s the most sensitive part of your body (non-sexual) when it comes to touch?
  • When did you first realize you were falling in love with me?
  • What’s something I haven’t done yet that you would love me to do?
  • If you could pick any character trait of mine to amplify, what would it be and why?

30 Juicy questions to ask your boyfriend

If you’re looking to ask more personal and intimate questions, consider these 30 revealing questions for your boyfriend. Remember, they’re quite personal, so be cautious and understanding if he’s not ready to answer them. These questions are better suited for couples who have been together for a while and know each other well.

  • What is your wildest fantasy that you’ve never shared with anyone?
  • Describe your most memorable intimate dream involving us.
  • What is the most daring place you would like to be intimate?
  • If you could choose any movie scene to recreate with me, which one would it be and why?
  • What kind of touch drives you absolutely wild?
  • Is there a specific outfit or costume you’d find irresistible on me?
  • What is a fantasy you think about often but haven’t told me yet?
  • How do you feel about using toys or props in the bedroom?
  • What’s something non-sexual that I do that turns you on?
  • What part of my body do you fantasize about the most?
  • Describe a scenario where you completely lose control with desire for me.
  • What kind of dirty talk do you find most arousing?
  • Is there a specific role or character you fantasize about me portraying?
  • What’s a kink or fetish you’re curious to explore?
  • How do you feel about watching adult content together? Any specific genre?
  • What’s the most sensitive part of your body that you love being touched?
  • Describe your perfect ending to a romantic date night.
  • What’s a sexual skill or technique you’re proud of?
  • What is your opinion on public displays of affection?
  • How do you feel about experimenting with different levels of dominance and submission?
  • What’s a sexual experience you’ve always wanted to have but haven’t yet?
  • What kind of lingerie or clothing do you find most seductive?
  • What’s something I do that unknowingly turns you on?
  • Describe a fantasy where you completely dominate the situation.
  • What are your thoughts on sensual massages leading to more?
  • How do you feel about trying long-distance sex toys ?
  • What’s an intimate act you’ve never done but are curious about?
  • Describe a situation that would be your ultimate tease.
  • What kind of foreplay do you think is underrated?
  • How do you feel about making our intimate moments more adventurous with games or challenges?

30 Funny Romantic questions to ask your boyfriend that with make him laugh

In a long-distance relationship, it’s important to find ways to keep the stay emotionally connected , whether you’re passing time during work hours, filling a quiet moment, or just looking to share a laugh together. Silly and fun questions are a great way to lighten the mood and enjoy each other’s company, even from afar. They aren’t just about deep discoveries; sometimes, it’s all about having a good time and sharing a smile.

Here’s a list of lighthearted questions to brighten up your long-distance conversations !

  • If we were superheroes, what would our powers be, and who would be the sidekick?
  • If you could choose any movie character to describe me, who would it be and why?
  • What’s the funniest dream you’ve had about us?
  • If we were both cats, what funny habits would we have?
  • If you had to serenade me with a song, which hilariously inappropriate song would you choose?
  • What’s the weirdest thing you thought about me when we first met?
  • If our love story was a comedy film, what would be its title?
  • Which cartoon character do I remind you of the most?
  • If we were a famous duo from history, who would we be and why?
  • What’s the funniest miscommunication we’ve ever had?
  • If you could pick a new name for me based on my quirks, what would it be?
  • What’s the most ridiculous outfit you could imagine me wearing?
  • If we were both animals in a zoo, what animals would we be and why?
  • What’s the funniest thing that could happen to us on a date?
  • If you had to compare our relationship to a food combo, what would it be and why?
  • What’s the funniest reason you can think about why we’d be late to an event?
  • If we were in a circus, what would be our acts?
  • Imagine we’re in a spy movie. What are our codenames and mission?
  • What’s the most absurd rule we would have if we ruled a kingdom?
  • If you could invent a fun holiday for us, what would it be called, and how would we celebrate it?
  • What’s the cheesiest pickup line you can think of using on me?
  • If we were in a video game, what kind of characters would we be?
  • What’s the funniest thing we could do if we became invisible for a day?
  • If our relationship was a dance, what dance would it be?
  • What’s the most ridiculous pet you can imagine us having?
  • If we had to use a tandem bike everywhere we went, how do you think it would go?
  • What would be the title of our autobiography?
  • If we were mythological creatures, which ones would we be?
  • What’s the most hilarious advice you’ve received about our relationship?
  • If we were both contestants on a cooking show, what disastrous dish would we accidentally make?

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I'm Jesse, your long-distance relationship expert. I share tips and advice on my blog to help you navigate the ups and downs of long-distance love. Whether you're just starting out or have been apart for years, my blog is here to help you stay connected and happy despite the distance.

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100 questions to ask your boyfriend

You’ve made it past the first date. And the second. And the third. Ea c h time, you dazzled this guy with your p e rsonality, impressed him with your intel ligence and probably make him laugh, too. Now that you’ve taken your relationship to the next level and he’s officially your boyfriend, open, honest communication is more important than ever.

One way to facilitate such dialogues is by asking good questions . Curiosity, after all, has the power to make or break a relationship. “Good, meaningful, foundationally-secure relationships with partners who are lovingly, vulnerably invested in the continuation of that relationship are so often tanked or ended by a lack of curiosity in both or one partner,” says psychotherapist Taylor Orlandoni, M.A., M.Ed., LMHC in New York City. “As soon as we stop being curious about our partner and their internal world, their desires, their hopes — we are at risk of simply assuming we know what our partner wants or means.” 

That’s why Oralndoni says so much of a couple’s work is in the reinstallation of curiosity. “You and your partner are constantly evolving and there is always more to learn,” she says, adding that questions can range from deep (“What’s something I do that makes you feel loved and safe?”) to playful (“If someone asked you to write a blurb about me, like the ones for authors on the jackets of their books, what would it say?”).

Ahead, there are 100 more questions to ask your boyfriend — whether you want to deepen your relationship or simply want a few conversation starters for long car ride.

Questions to ask your boyfriend anytime

  • What’s a food you’ve been craving recently that you want to cook together this weekend?
  • What’s your favorite movie or TV character from childhood?
  • What’s an interesting podcast you listen to that you think I would like too?
  • What’s the best piece of advice you’ve gotten this week?
  • If you could be any video game character, who would you pick?
  • If you could invent a new ice cream flavor, what would you call it?
  • Is there anything new you’re passionate about lately?
  • If you won $1 million but could only spend it on an experience, what would it be?
  • If you could attend any sports game in history, what would it be?
  • If you could have any super power for the rest of your life, what would you choose?
  • What’s an athletic challenge that’s a dream of yours to complete?
  • If you could live during any era but this one, which would you pick?
  • What’s your favorite thing to do after work?
  • What do you get complimented on the most?
  • If money were no issue, where would we go on vacation?
  • What’s the funniest thing to happen to you all month?
  • Do the holidays stress you out or do they make you happy?
  • What’s a collection you wish you started years ago?
  • What does your perfect day with friends look like?
  • What’s your favorite place to visit in your neighborhood?

Serious questions to ask your boyfriend 

  • Do you have any regrets about our relationship?
  • What do you see for our future?
  • Do you think we’ll move in together?
  • What’s your biggest fear about our relationship?
  • What could I do to support you better in our relationship?
  • What’s your attachment style?
  • What’s your love language ?
  • Do you think we handled [XYZ] fight well?
  • How could we communicate better as a couple?
  • When you’re in a bad mood, what should I do?
  • Do you hope to get married one day?
  • Do you hope to have a child or children one day?
  • Would you ever relocate for our relationship if I had to move somewhere else?
  • Could you be in a long-distance relationship ?
  • When did you know you wanted to be my boyfriend?
  • How would you describe our relationship to others?
  • Do you feel like we spend the right amount of time together?
  • Do you see us as compatible long-term?
  • What do your closest loved ones think about our relationship?
  • Do you feel like we’re putting in equal effort into our relationship?

Reflective questions to ask your boyfriend

  • What’s your favorite thing about our relationship?
  • What’s an area for improvement in our relationship?
  • Do you have a favorite memory of us?
  • When I’m having a tough time, how does that make you feel?
  • Is our relationship moving at the right pace?
  • Is there anything you wish we had done differently so far in our relationship?
  • What are you most proud of when you think about our relationship?
  • Do you think we both trust each other fully?
  • How is this relationship different from your previous ones?
  • When you’re upset with me, how do you think you handle it?
  • What do you value most about our bond?
  • What’s the most important lesson our relationship has taught you?
  • What’s the ideal amount of time for you to date before getting engaged?
  • Am I different with you in groups than I am alone?
  • Are there any goals you’d like for us to achieve together?
  • How do you think our relationship has evolved?
  • Has your outlook on love changed since we started dating?
  • Do any areas of our relationship need more attention?
  • How do you prioritize our relationship in your life in ways I may not know?
  • What’s something we could regularly do together to strengthen our relationship?

Sweet questions to ask your boyfriend

  • Do you have a favorite ritual that we do together?
  • Are there any love stories that remind you of us?
  • What do you think your loved ones who are no longer with us would say about our relationship?
  • Are there ways I can step up to help you this week?
  • What errand of yours can I run to make your life easier?
  • What’s the nicest thing I’ve ever done for you?
  • What’s a memory of us that always makes you smile?
  • What’s a song that always reminds you of us?
  • Can I share with your family and friends that you did [XYZ] for me?
  • What ways do you think we complement each other best?
  • How many days can you go without missing me too much?
  • What’s a new way that I can show you I love you?
  • Are there any ways I’ve influenced you for the better?
  • What words come to mind when I ask you to describe having me in your life?
  • What lesson do you think could help others from our relationship?
  • Are there any small things I’ve done for you that made you feel extra loved?
  • What’s your favorite gift you've received from me?
  • Do you think we might stay in the honeymoon phase forever?
  • Do you think about me when we’re apart?
  • Do I show up in your dreams?

Random questions to ask your boyfriend

  • Sweet or savory?
  • Snow sports or water sports?
  • What’s your favorite Broadway show?
  • What do you think of horoscopes?
  • What’s one talent I’d be surprised to learn you have?
  • What’s your favorite kitchen tool?
  • What actor would play you in a feature film biopic?
  • How long could you stay indoors without going stir-crazy?
  • Are there any musicians you’d love to see live for the first time?
  • What’s your favorite time of day?
  • Glamping or camping?
  • What’s the best newsletter in your inbox?
  • Have you ever seen a psychic?
  • Fresh flowers or houseplants?
  • Hot sauce or barbecue sauce?
  • Beach or lake?
  • Physical books or e-books?
  • Cold shower or hot shower?
  • Plain water or sparkling water?
  • Do you make New Year’s resolutions?

More ways to grow your relationship

  • A relationship coach shares tips for happy, long-lasting connections
  • 50 love quotes that will warm his heart
  • 130 questions for couples to ask anytime

travel questions to ask your boyfriend

Perri is a New York City-born-and-based writer. She holds a B.A. in psychology from Columbia University and is also a culinary school graduate of the Natural Gourmet Institute. She's probably seen Dave Matthews Band in your hometown, and she'll never turn down a bloody mary. Follow her on Twitter  @66PerriStreet  or learn more at  VeganWhenSober.com

286 Questions to Ask Your Boyfriend (For Any Situation)

286 Questions to Ask Your Boyfriend (For Any Situation)

How well do you know your boyfriend? Like, really know him? It doesn’t matter if you have been dating for a few months or a few years; there is always more to learn about the person you’re with.

Whether you are in the beginning stages of your connection and are in need of inspired conversation starters to help you get to know each other better, or have been dating for quite some time and are looking for the right questions to ask to deepen your relationship with your significant other, you have come to the right place.

The questions in this article are great to ask either over text to keep a conversation interesting or as conversation topics to cover on your next date night.

Relationship compatibility

  • About your relationship
  • About the future
  • Before moving in together
  • Before getting engaged

His life and family

His worldview and values, his life goals.

  • Truth or dare

Common questions and important considerations

Important and serious questions to ask your boyfriend.

When you are hoping to take any relationship to a deeper level there are certain questions that are important to ask. Here are 50 questions that will help you to gain clarity around your relationship.

When you start dating someone new, it can be easy to get lost in chemistry and physical attraction. While both of these things are important parts of being with someone romantically, they are not the only things that matter. It might feel scary bringing topics up like this with a new boyfriend, but don’t be so afraid of asking the wrong question that you end up wasting time with someone who isn’t compatible.

1. Are you a night owl or early bird? &nbsp 2. Do you like moving around or prefer to be settled in one place? &nbsp 3. Are you adventurous or more of a homebody?

4. How do you envision your perfect day? &nbsp 5. Do you see yourself wanting kids one day? &nbsp 6. How important to you is self-development?

7. How do you deal with stress in your life? &nbsp 8. How do you express love in a relationship? &nbsp 9. Would you consider yourself to be a workable partner?

10. How do you envision splitting finances with your partner?

Questions to ask your boyfriend about your relationship

It’s never a bad idea to check in with your partner to see how both of you are feeling about your relationship and figure out if there are any areas that need extra attention. By creating an open and ongoing conversation about the ways that you can connect and support each other more deeply, you are much more likely to have a relationship that lasts. Help build deep intimacy with the following questions.

1. When we fight, do you feel like we resolve the issue? &nbsp 2. Are there any ways I could make you feel more loved? &nbsp 3. What is your favorite part of being with me?

4. Can you see us being together long-term? &nbsp 5. Do you feel supported by me in our connection? &nbsp 6. Do you feel safe bringing up serious issues with me?

7. Is there anything you feel is lacking in our relationship? &nbsp 8. What’s your happiest memory with me? &nbsp 9. Do you feel respected by me?

10. When do you feel the closest to me?

Serious questions to ask your boyfriend about the future

Being aware of the dream that you have for the future and the way that your partner fits into it is an important piece in being able to make it a reality. Spend some time getting clear on your vision, and then share your goals for the future with your partner. By doing so, you two have the opportunity to collaborate on making it a reality.

1. If we bought a house, where would you want it to be? &nbsp 2. What is a goal of yours for our relationship? &nbsp 3. Are there any aspects of our relationship that you don’t think are sustainable long-term?

4. Do you see yourself wanting to have kids with me? &nbsp 5. What are your financial priorities? &nbsp 6. Where do you see us in 5 years?

7. Can you see yourself being in the same career long-term? &nbsp 8. When you picture yourself at 50, what do you see? &nbsp 9. How important is having a family to you?

10. Is there anything on your bucket list that we could do together this year?

Questions to ask your boyfriend before moving in together

Moving in with your boyfriend is a big decision and one that should not be made lightly or for the wrong reasons. Regardless of how much you love your partner, there are issues every couple faces when trying to organize everyday life with someone new. Take time to understand what you and your partner need to make home life work for both of you before making the big move. Find out if you’ll make good housemates with the following 10 questions.

1. On a scale from 1-10, how clean do you want your house to be? &nbsp 2. How do you envision sharing household responsibilities &nbsp 3. How much alone time do you need?

4. Do you like entertaining guests or prefer to have the house to yourself? &nbsp 5. What is our intention for moving in together? &nbsp 6. How do you envision us spending a day together?

7. How would you like to split household expenses &nbsp 8. When we’re fighting, do you need time to process or want to resolve it immediately? &nbsp 9. How much physical space do you need for yourself in the house?

10. Do you prefer cooking at home or eating out?

Questions to ask your boyfriend before getting engaged

If you are considering getting married to someone, then it’s important to not be too shy to ask important compatibility questions before doing so. You need to make sure that you are with someone who you can have uncomfortable conversations with. An important part of healthy relationships is open communication. Don’t avoid difficult conversations. Get to know your potential husband better by asking the following questions before marriage.

1. Who are your relationship role models? &nbsp 2. If we do have kids, how do you envision splitting the parenting responsibilities? &nbsp 3. Would you feel comfortable supporting your partner to be a stay-at-home mom?

4. How do you feel about the idea of being with only one person sexually for the rest of your life? &nbsp 5. How important is buying nice things to you? &nbsp 6. What are your priorities in life? Can you ever see them changing?

7. Is my debt your debt? &nbsp 8. How did your family deal with conflicts? Is that how you still deal with conflicts? &nbsp 9. How important to you is open communication?

10. Do you picture us doing everything together or still having autonomy?

Romantic questions to ask your boyfriend

In long-term relationships, the “feel-good” chemicals wear off after a while, and it might feel like the romance is fading. [ 1 ] This can be attributed to why a lot of couples feel as though their relationship loses its spark over time. If you are dedicated to keeping romance alive with your partner, here are some great questions to ask while texting and in person during your next date night.

1. Do you know how handsome I think you are? &nbsp 2. When do you feel the sexiest? &nbsp 3. Do you still get butterflies when I call or text you?

4. Can you see us growing old together? &nbsp 5. What’s your favorite pet name that I’ve given you? &nbsp 6. When we’re apart, what do you think about me the most?

7. What is your love language? &nbsp 8. What is your dream vacation with me? &nbsp 9. What do you think is your superpower?

10. What is a romantic fantasy of yours? &nbsp 11. How would you spend the perfect night with me? &nbsp 12. When do you feel the most loved by me?

13. What do you think is my favorite part of you? &nbsp 14. What is a relationship dream you have with me? &nbsp 15. How much do you love making love to me?

16. How adorable would our babies be? &nbsp 17. What’s your favorite time of the day to be intimate with me? &nbsp 18. What is your favorite memory of us together?

19. What’s your favorite thing about being intimate with me? &nbsp 20. Do you think love at first sight is real? Is that how you felt with me? &nbsp 21. Where is your favorite place to be with me?

22. What song makes you think about me? &nbsp 22. If our relationship ended, what would you miss the most about me?

Fun questions to ask your boyfriend

If you are looking for some good and fun questions to ask your boyfriend to make him laugh, these are the perfect choice for you. Not everything always has to be serious, and sometimes simply sharing a laugh with him is exactly the kind of connection your relationship needs.

1. What is one toy you always wanted as a kid? &nbsp 2. What is the most “unmanly” thing you do? &nbsp 3. What game or reality show do you think you would do really well on?

4. Be honest, do you prefer being the big or little spoon? &nbsp 5. What did you want to be when you grew up? &nbsp 6. Do you think you could be with me if I was 1ft taller than you?

7. How seriously do you take horoscopes? &nbsp 8. What fictional place would you visit if you could? &nbsp 9. If you could choose any language to immediately be fluent in, what would you choose?

10. What book or movie are you embarrassed to admit you like? &nbsp 11. If you had to marry one of your best guy friends, who would you choose? &nbsp 12. Would you rather be able to eat anything you want and never gain weight or be able to read people’s minds?

13. Would you ever come for a mani-pedi with me? &nbsp 14. Would you get a tattoo on your butt for $1000? &nbsp 15. Would you rather meet an alien or a ghost?

16. What is a random job that you think you would be really good at? &nbsp 17. How long do you think you would last alone on a desert island?

Deep questions to ask your boyfriend

An easy way to strengthen the bond you have with your boyfriend is by asking deep questions about them and listening closely to the answers. By asking the right questions, you will be able to learn intimate details about his past, and often this gives beautiful insights into how their past continues to shape their present reality. Get to know your boyfriend better with these deep questions.

1. What’s one thing you’re glad you’ll never have to do again? &nbsp 2. Do you think that any two people can be in a healthy relationship as long as they communicate well? &nbsp 3. Do you feel like your parents did a good job of raising you?

4. What do you consider to be the hardest day of your life? &nbsp 5. Do you have any regrets? &nbsp 6. Do you feel free in your life?

7. Are you happy overall with your life as it is right now? &nbsp 8. What aspect of your life do you find the most fulfilling? &nbsp 9. Do you have any dreams that you’re afraid to pursue?

10. What’s the best piece of advice anyone has ever given you? &nbsp 11. What has been the biggest blessing in disguise in your life? &nbsp 12. Did COVID change your life for the better in any way?

13. What is one time that you wished you could slow down time? &nbsp 14. If you could write a note to your younger self, what would it say? &nbsp 15. Have you ever struggled with mental illness?

16. What is one quality about yourself you wish you could change? &nbsp 17. What do you consider to be your most unloveable quality? &nbsp 18. Do you ever struggle with jealousy in our relationship?

19. Where would you live if money and work weren’t a factor?

Cute questions to ask your boyfriend

If you are bored and want to put in some work to keep your man wrapped around your finger, then try adding a few of the following questions into your next conversation with him. They are great to be used in person but will also hit home if you use them over text as well. Enjoy embracing your cuteness with the following questions.

1. If I was a flower, what do you think I would be? &nbsp 2. What is the biggest feeling you experience while we are together? &nbsp 3. Do you still smile when you see you have a text from me?

4. What reminds you of me? &nbsp 5. How would you describe how I smell? &nbsp 6. Do you ever think about me during the day?

7. When do you feel the most connected to me? &nbsp 8. How adorable do you think our kids would be? &nbsp 9. What would you want to name our son?

10. What animal do you think I’m the most similar to? &nbsp 11. Do you think I could ever be too in love with you? &nbsp 12. What do you see when you imagine our future together?

13. What’s your favorite pet name to call me? &nbsp 14. If I’m feeling sad, what do you know will cheer me up? &nbsp 15. What is one quirky quality of mine that you love?

16. Do you still love holding my hand? &nbsp 17. If you wrote a song about me, what would you call it? &nbsp 18. What is the sweetest thing you think I’ve ever done for you?

19. How would you feel if I bought you flowers?

Flirty questions to ask your boyfriend

If you’re the kind of person that feels nervous being flirtatious or suggestive, then using these questions as a way to break the ice might be a great start for you. Let your boyfriend see a more fun and confident part of your personality by asking the following flirtatious questions next time you see him.

1. What do you think I’m wearing right now? &nbsp 2. Would you rather see me naked or in lingerie? &nbsp 3. Do you know how badly I want you right now?

4. What’s one thing you want to do with me that you’ve never done before? &nbsp 5. How did you feel when we had our first kiss? &nbsp 6. What do you think is my favorite part of your body?

7. What’s the sexiest dream you’ve ever had about the two of us? &nbsp 8. How many times did you want to kiss me before our first kiss? &nbsp 9. What’s your favorite part of my body?

10. Would you ever go skinny dipping with me? &nbsp 11. Would you ever take a bath with me? &nbsp 12. Would you rather see me in a cute dress or a revealing workout set?

13. How do you feel when you stare into my eyes? &nbsp 14. Would you eat food off of my body? &nbsp 15. What would be your favorite way for me to wake you up?

Intimate questions to ask your boyfriend

At a certain point in your relationship, you need to let go of your fear of asking more personal questions and start creating a more intimate relationship with your partner. Although it might feel scary, the truth is that asking intimate questions to the right person will not scare them away and will instead only work to strengthen the connection between the two of you.

1. Who was your role model growing up? &nbsp 2. When was the last time you cried? &nbsp 3. Do you feel comfortable crying in front of me?

4. How important is physical attraction for you in pursuing a woman? &nbsp 5. What were you most afraid of as a kid? &nbsp 6. What’s your biggest fear as an adult?

7. Do you consider yourself to be more of an introvert or extrovert? &nbsp 8. If you could choose one big decision from your past to change, what would it be? &nbsp 9. Are there any things that you do to show me love that you think I don’t notice or appreciate?

10. Do you feel safe in our relationship? &nbsp 11. What do you feel is your biggest talent in life? &nbsp 12. What is a dream of yours that you aren’t pursuing right now?

13. When in your life have you felt the most heartbroken? &nbsp 14. How free do you feel in your life? &nbsp 15. What is your definition of freedom?

16. Is there anything that I make you feel insecure about? &nbsp 17. What is something I could do right now to improve your life? &nbsp 18. Do you view yourself as more of a nurturer or a protector?

19. Do you think that you have changed a lot this past year? &nbsp 20. What are three words you would use to describe yourself? &nbsp 21. What is an insult someone said to you that still affects you to this day?

22. Do you consider yourself to be a workable person? &nbsp 23. What weird quirks does your body have?

Questions to ask your boyfriend about you

Have you ever thought to yourself, “I wonder what my boyfriend really thinks about me?” Now is the perfect opportunity for you to find out. Don’t be afraid to ask questions about yourself. His answers will be a great insight into how he feels about you, and hopefully they will leave you feeling deeply loved and understood by your partner.

1. Do you think that I make you a better person? &nbsp 2. What is your favorite feature of mine? &nbsp 3. What would be the best thing about growing old with me?

4. Is there anything I have helped you learn about yourself? &nbsp 5. When you’re sick, do you think that I take good care of you? &nbsp 6. What do you think is my greatest strength?

7. What is something that I could benefit from working on? &nbsp 8. When did you know you were in love with me? &nbsp 9. Do I make you feel respected?

10. When do you think I look the sexiest? &nbsp 11. What was your first impression of me? &nbsp 12. How would you describe me to a friend?

13. If we had kids, what features of mine would you want them to have? &nbsp 14. Is there anything you’ve always wanted to ask me but haven’t? &nbsp 15. What about me made you want to be with me?

16. What do you think would be a perfect job for me? &nbsp 17. What is a quality of mine that you most admire? &nbsp 18. Do you think I would be a good mother?

19. What do I do that makes you feel the most loved? &nbsp 20. What trait of mine first drew you towards me? &nbsp 21. Do you ever dream about me?

22. Do you like kissing or hugging me more?

Questions about him

These are good questions that have been specifically created for you to use to get to know more about your boyfriend in specific intimate areas of his life.

A person’s past plays a big role in who they are, and you can learn a lot about your partner by understanding the challenges, triumphs, and any embarrassing moments that have shaped who he is as a person. Have you always wondered about the experiences that make your boyfriend the man you know and love? Use these questions to get to know more about his past.

1. What has been the saddest day of your life? &nbsp 2. What is an experience from your childhood that you feel still deeply impacts you to this day? &nbsp 3. What was school like for you growing up?

4. Did you have any pets growing up? &nbsp 5. What is something that has always made you happy? &nbsp 6. Is there anything about your life that you would want to change?

7. What is the hardest thing you’ve had to do alone? &nbsp 8. What is a challenge that you overcame and taught you important life lessons? &nbsp 9. What in your life do you feel the most proud of?

10. Why did you and your last ex break up?

Many studies have found links between parental behavior during a person’s childhood and their behavior as an adult. [ 2 ] If you want to gain a deeper understanding of the habits and perspective of your partner, learning more about his relationship with his parents and family as a whole is a great way to do so. The following questions will give you meaningful insight into the role that your boyfriend’s family plays in his life.

1. Do you feel like you were nurtured enough by your parents? &nbsp 2. What’s your favorite childhood memory with your family? &nbsp 3. Do you ever wish your parents did a better job of raising you?

4. What’s the best advice that your parents have ever given you? &nbsp 5. What is your favorite thing about your mom? &nbsp 6. Do you see your parents more as parents or friends?

7. Who in your family would you go to if you needed support? &nbsp 8. Do you have a large extended family? Are you close with them? &nbsp 9. Did your parents set a good example of healthy relationships for you growing up?

How your partner sees the world will definitely play a role in how easy it is for the two of you to have long-term longevity. Although you can have a connection that is largely based on chemistry or physical attraction with just about anyone, being with someone who shares the same opinions and values with you will make life with them that much easier. These are great questions to ask in order to figure out if you and your partner share similar views and values.

1. Do you think that everything happens for a reason? &nbsp 2. Do you think that hard times make you bitter or better? &nbsp 3. Were you raised with any beliefs that you now reject?

4. Do you value money or close relationships more? &nbsp 5. What is one really positive value that your parents instilled in you? &nbsp 6. Who shaped a lot of the values you still carry?

7. What is a value of mine that you really admire? &nbsp 8. What is a value that you think the two of us share? &nbsp 9. How important is money to you?

Knowing what your partner sees in his future is a great way to figure out if you two have long-term potential. If your vision for the future doesn’t align with his, then there is a chance the two of you have an expiration date, so making sure you two are on the same page early on is important. Find out the direction your boyfriend is headed by asking him the following questions.

1. Where do you see yourself in one year? &nbsp 2. Where do you see yourself in five years? &nbsp 3. Are you interested in creating a business together?

4. In what areas of your life do you have goals set right now? &nbsp 5. Is personal development important to you? &nbsp 6. How dedicated do you feel to improving yourself?

7. Are you good at following through when you set goals for yourself? &nbsp 8. What are some ways that you self-sabotage your own success? &nbsp 9. Is there anything I can do to help support you in reaching your goals?

10. What is one daily goal you could set for yourself right now that would greatly improve your life?

Hard questions to ask your boyfriend

Some of the best things in life don’t come easy, and answering these questions isn’t an exception. Waiting for the right time to ask these questions is important because they are deeply personal, and it may be hard for someone to share intimate details about themselves. Asking difficult questions may be a little uncomfortable, but your boyfriend’s answers will help you understand him in a much more meaningful way.

1. Does the idea of being in love scare you? &nbsp 2. Would you want to know the day or how you are going to die? &nbsp 3. Is there anything about you I don’t know and would make me question our relationship?

4. What do you think is the weakest part of our relationship? &nbsp 5. Is there anything about me that makes you question being with me? &nbsp 6. What would it look like if you fully lived up to your potential?

7. What is more important in a relationship, physical attraction or friendship? &nbsp 8. What is something that you have trouble accepting even if you know that it’s true? &nbsp 9. Are there any negative qualities about yourself that you’re worried you’ll never be able to change?

10. Are there any ways that you feel like your parents kind of messed you up? &nbsp 11. Is there anyone in your life that you hate? &nbsp 12. What is the most hurt you’ve ever felt by another person?

13. Have you ever been physically or emotionally abused? &nbsp 14. Is there anything you have ever wanted to tell me that you haven’t had the guts to? &nbsp 15. Do you think you could ever forgive me if I cheated on you?

16. What event has made you mature the most as a person? &nbsp 17. Do you find it easy to ask others for help? &nbsp 18. What is one thing that you know when it happens is going to break your heart?

19. If you died tomorrow, do you think you would die happy? &nbsp 20. When was the last time you stepped outside of your comfort zone? How did it feel? &nbsp 21. What physical feature of yours do you feel the most self-conscious about?

Weird questions to ask your boyfriend

Not all conversations need to be really deep. If you want some good questions that are sure to make your boyfriend laugh and allow the two of you to connect in a fun, non-sexual way, then these will be great options for you. Deepen your friendship and have fun laughing with your boyfriend by asking him these questions.

1. If you had a pet unicorn, what would you name it? &nbsp 2. Do you pee in pools? &nbsp 3. If you could be a cartoon character, who would you choose?

4. What’s something you love that other people think is gross? &nbsp 5. If you could have any animal as a pet, what would you choose? &nbsp 6. What is the best organ?

7. Do you wear clothes at home or hang out completely naked? &nbsp 8. Where was the worst place you’ve ever farted? &nbsp 9. Do you ever talk to yourself in the mirror?

10. How long do you think you’d survive a zombie apocalypse? &nbsp 11. If you had to kiss another guy, who would you choose? &nbsp 12. What is something that is always on your grocery list?

13. If you catch a fish, do you eat it or let it go? &nbsp 14. Would you ride on the back of my motorcycle? &nbsp 15. What do you usually do while you’re pooping?

Random questions to ask your boyfriend

If you want to keep your boyfriend on his toes and make him laugh, then these are great conversation starters for you to use. Not every conversation you have has to be deep and meaningful, so kick back, relax and enjoy asking your special someone the following random questions.

1. How often do you get in fights with strangers on the internet? &nbsp 2. Is there anything that you’re obsessed with? &nbsp 3. What is the best part about being a boy?

4. Would you rather eat McDonald’s or a salad? &nbsp 5. If you could only wear one thing for the rest of your life, what would you choose? &nbsp 6. What is the weirdest crush you’ve ever had?

7. If I had something on my face would you tell me? &nbsp 8. Do you think you could pull off glasses? &nbsp 9. Who is your favorite cartoon character?

10. If you found 5 dollars on the ground, what would you do with it? &nbsp 11. Would you rather live in a desert or Antarctica? &nbsp 12. If you could swap lives with one of your friends, who would you choose and why?

13. Would you get matching tattoos with me? &nbsp 14. If you could live as an animal for a year, what would you choose? &nbsp 15. Would you rather look like a potato or feel like a potato?

16. What is the worst thing about being a guy? &nbsp 17. Would you let me do your makeup?

Truth or dare questions to ask your boyfriend

As cheesy as playing truth or dare might seem, it’s actually a really fun and easy way to connect with your partner. Having fun in your relationship is an important part of keeping chemistry alive long-term. Asking simple, lighthearted questions like these can help you get to know each other better and have fun while doing so.

1. Your most embarrassing moment with a girl? &nbsp 2. How do you feel about your ex-girlfriend now? &nbsp 3. If me and your best friend were in trouble, who would you help first?

4. What’s a fantasy of yours that you’ve always been afraid to share with me? &nbsp 5. Is there anyone you stalk on social media? &nbsp 6. When was the last time you lied to me?

7. What do you do when you’re at home alone? &nbsp 8. What is a habit of yours that you think I’d be grossed out by? &nbsp 9. Is there anything about me that really annoys you but you don’t have the heart to tell me?

10. What did you think about me when we first met? &nbsp 11. What is the hardest thing about being a boy? &nbsp 12. Is there anyone you kissed while drunk that you regret kissing?

13. What is the weirdest dream you’ve ever had? &nbsp 14. What is the worst gift someone has ever given you? &nbsp 15. Are there any friends of mine that you don’t like?

16. What is my worst quality? &nbsp 17. If you could go on a date with any celebrity, who would you choose? &nbsp 18. On a scale from 1-10, how good do you think I am in bed?

How to know what questions to ask your boyfriend

If after reading this article you are wondering how to choose the right question for your relationship, then here are some things to keep in mind.

58% of men feel under pressure to be emotionally tough and feel that they can’t show any weakness. [ 3 ] This shows that when it comes to deep conversations about emotions, your boyfriend might enter the conversation feeling guarded and uncomfortable about expressing emotion and being possibly perceived as weak.

While speaking about deep, personal topics might be comfortable to you, it is possible that another person will not share this same level of comfort when it comes to opening up. What is appropriate to ask will depend largely on your specific relationship and how comfortable your partner is sharing intimate details about their life.

The lighter categories in this article are appropriate to ask in most situations and do not involve a lot of discretion, but when asking more personal questions, it is important to monitor your boyfriend’s reactions. If he is avoiding eye contact or his body language indicates he is feeling uncomfortable, then it is best to end the conversation and ask him how you can help him to feel loved and safe in that moment.

When is the right time to ask these questions?

Asking questions about your boyfriend is a generally good way to make him feel as though you are interested in getting to know him on a deeper level, and a lot of people feel very loved by this kind of attention.

When it comes to lighthearted questions, there is generally no ”‘wrong” or “right” time to ask them. If your boyfriend is feeling tired or like he doesn’t have the space to answer questions at that moment, then that is a boundary that should be communicated by him clearly and lovingly.

When it comes to more personal questions, it is important to be intentional about when you ask them. Generally, this should not be when your partner has had a long day or is in a noticeably bad mood. It is important to wait for a time when you feel like the two of you can connect without interruption and both feel safe to let your guard down.

If your boyfriend is blessing you by letting his guard down and letting you know more intimate details about himself and his life, make sure that you make listening to him your number one priority.

What to talk about with your boyfriend

When it comes to what to talk about with your boyfriend, it’s best not to overthink it. If you are nervous asking questions, start with light, fun conversation topics that feel more comfortable. As you gain more courage, you can begin asking more flirty and suggestive questions, and chances are your boyfriend will love it.

The important thing to remember here is that nothing is really that serious, and the experience of getting to know your partner is supposed to be fun. If you’re with someone that doesn’t appreciate you wanting to get to know them better, that’s not a “you” problem.

Why using questions to test your boyfriend can damage your relationship

If you have access to the internet, you have no doubt seen some of the toxic relationship advice that makes its way around platforms like Instagram and Tik Tok. While this advice may be funny, it can also be incredibly damaging to implement in your romantic life, and using questions that are designed to test your partner is one of the ways that you can ruin your relationship with a potentially great match.

No one likes to feel like people are asking them questions that are intended to be manipulative and coercive, least of all the person they are involved with romantically. When you play games with your boyfriend, it’s very possible that he will begin to feel as though you do not respect him, and it could severely damage the trust in your connection. It’s difficult to feel safe in a connection that doesn’t have a strong foundation of trust, and using trap questions to test your boyfriend is an easy way to erode your connection with him.

  • Lebow, H. I. (2021). Ways to Keep Romance Alive. Psych Central .
  • Akhtar, A. (2020). 11 science-backed ways your parents’ behaviors shaped who you are today . Business Insider .
  • Gonsalves, K. (2019). Study Shows Men Still Feel Judged When They Talk About Their Feelings . Mindbodygreen .

travel questions to ask your boyfriend

Viktor is a Counselor specialized in interpersonal communication and relationships. He manages SocialSelf’s scientific review board. Follow on Twitter or read more .

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180 questions to ask your boyfriend, 180 questions to ask your girlfriend.

Your boyfriend lived a whole life before you arrived on the scene, complete with embarrassing moments, great achievements, and failed relationships. If you want to learn more about his past and what makes him tick, you need to know what questions to ask.

Read on for over 100 questions to ask your boyfriend, from serious and romantic to fun and cute. Whether you've been together for six weeks or six years, these questions are the perfect way to open up communication, create intimacy, and get to know your partner better.

Deep Questions to Ask Your Boyfriend

If your relationship is starting to get serious, it's important to know if you and your boyfriend have the same values, desire the same kind of life, and want the same type of relationship. It's also helpful to know about issues in his past and how he prefers to be treated in a relationship. The following important questions to ask your boyfriend will give you the answers you need, and will help you get to know him on a deeper level.

  • Do you want to have children?
  • How long was your longest relationship? Why did it end?
  • Have you ever been engaged or married? Do you ever want to get married?
  • Have you ever lived with a partner?
  • How important is religion or spirituality to you?
  • How do you feel about gay rights?
  • Do you think money can buy happiness?
  • What is your dream job?
  • What one thing do you want to accomplish in your life?
  • What accomplishment are you most proud of?
  • What are you afraid of?When was the last time you voted?
  • How would you describe your relationship with your family?
  • Do you have a best friend?
  • What is your love language?
  • Are you an introvert (those who recharge by being alone) or an extrovert (those who feel energized from being around other people)?
  • Do you hold grudges?
  • Have you ever struggled with addiction?
  • Have you ever been in an emotionally or physically abusive relationship?
  • Do you think a relationship can come back from cheating?

Cute Questions to Ask Your Boyfriend

Getting to know your new partner doesn't have to be so serious. These cute questions to ask your boyfriend will shed some light on his childhood adventures, favorite memories, and personal preferences.

  • Who was your role model growing up?
  • When you were a kid, what career did you want to have?
  • Did you go to summer camp?
  • What is your idea of a perfect Sunday afternoon?
  • What is your favorite holiday?
  • What is the best present you've ever received?
  • What did you and your friends do for fun in middle school?
  • Did you have any pets growing up?
  • What is your happiest childhood memory?
  • If you could cook any dish perfectly, what would you choose?
  • When you're having a bad day, what makes you feel better?
  • At an amusement park, what ride do you just have to go on?
  • What toy did you always want as a kid, but no one ever bought for you?
  • Did you ever sleep with stuffed animals?
  • What sound do you love?
  • What are your favorite scents?
  • What candy do you hate?
  • What is your favorite karaoke song?
  • What was your favorite thing to do during recess?
  • What is your favorite thing to do on a rainy day?

Fun Questions to Ask Your Boyfriend

Sometimes it's hard to know what questions to ask your partner to get to know him better. Here are some funny questions to ask your boyfriend, and will get you laughing and bonding in no time.

  • What is the weirdest reason you ever broke up with someone?
  • When was the time you laughed the hardest?
  • If you could listen to only one song for the rest of your life, what song would you choose?
  • What celebrities have you met?
  • What word do you hate?
  • What is your pop culture guilty pleasure?
  • What is the most embarrassing thing that ever happened to you?
  • What is the weirdest thing you've ever bought?
  • Have you ever been to a palm reader?
  • Who would you rather hire: a personal trainer, a personal chef, or a housekeeper?
  • What would you do if you could be a woman for a day?
  • What is the one movie you've seen more times than you can count?
  • If a movie was being made about your life, what actor would play you? What actress would play your love interest?
  • What were you like in high school?
  • What fictional character do you relate to the most?
  • Would you rather be hot or cold?
  • If you could be born in a different decade, what decade would you choose?
  • What is your favorite part about being an adult?
  • Have you ever played Truth or Dare? What was the most memorable dare that you accepted?

Dirty Questions to Ask Your Boyfriend

If you want to heat things up in your relationship, you'll need to talk about sex. Learn what turns him on and improve your sex life with these sexy questions to ask your boyfriend.

  • In an ideal world, how many times would you have sex in a week?
  • What is something you've always wanted to try in bed?
  • Have you ever had/would you ever have a threesome?
  • Have you ever been attracted to a man?
  • How did you lose your virginity?
  • When was the first time you ever masturbated?
  • What is your number one sexual fantasy? Would you ever do it in real life?
  • Where is your favorite place to have sex outside of the bedroom?
  • Have you ever been walked in on during sex? Have you ever walked in on someone else?
  • What is the craziest thing you've ever been asked to do in bed? Did you do it?
  • How do you feel about porn? What kind of porn do you like?
  • What is your favorite sexual position? What is your least favorite sexual position?
  • What are your most sensitive erogenous zones that don't always get attention? (Nipples, ears, neck, etc.)
  • What is your favorite part about sex? (Foreplay, teasing, penetration, oral sex, pillow talk, etc.)
  • If we were going to role play, who would you want me to dress up as?
  • Have you ever/would you ever go to a dominatrix?
  • What sex toy have you been dying to try?
  • What words or sexy phrases turn you on?
  • What is the weirdest thing that turns you on?

Good Questions to Ask Your Boyfriend

  • When you've been in a relationship for a while, it can be hard to come up with new things to talk about. These interesting questions to ask your boyfriend are a great way to ensure that there's never a dull moment between the two of you.
  • Where is your ideal place to live? On a farm in the middle of nowhere, in an elegant house on the water, or in a hip, downtown condo?
  • What do you want to do when you retire?
  • What is your ideal vacation? Staying at an all-inclusive resort in Maui, sightseeing in London, or camping at Yosemite National Park?
  • What is your favorite city?
  • If you could have any skill without having to work for it, what would it be?
  • Do you think it's possible for men and women to just be friends?
  • How do you like to be treated when you're sick? Do you like to be waited on hand and foot or left alone?
  • Do you have any phobias? (Spiders, heights, germs, etc.)
  • What is your biggest pet peeve?
  • What cause have you volunteered for that you feel passionately about?
  • If you were going to start a charity, what would it be for?
  • Do you watch, read, or listen to the news?
  • What is the best advice anyone ever gave you?
  • Do you like talking on the phone?
  • What are your relationship deal breakers?
  • What relationship cliché do you think is true?
  • If you had to go back to school, what would you study?
  • What is your favorite time of year?
  • What motivates you?
  • What has been the best year of your life so far?

Random Questions to Ask Your Boyfriend

Your partner probably has great stories that you've never heard, because they've never come up in conversation. These weird questions to ask your boyfriend will get him talking about his most epic moments.

  • What fictional character do you have a crush on?
  • Do you believe in ghosts?
  • Have you ever pranked anyone? Have you ever<em> been</em> pranked?
  • If you could eat only three foods for the rest of your life, what three would you choose?
  • If you could trade places with one person for a day, who would it be?
  • What is your hidden talent?
  • Do you ever feel like you had a past life?
  • Have you ever broken any bones?
  • If you were going to get a tattoo today, what would it be of?
  • If you could inhabit any movie, TV show, book, or other fictional universe, where would you live?
  • Do you collect anything?
  • What is your theme song?
  • If you could wake up tomorrow and be fluent in any language, what language would you choose?
  • Do you have any superstitions?
  • If you could go back to any moment in your life and do things differently, would you?
  • Have you ever been skydiving?
  • Have you ever tried to invent something?
  • Would you ever go on a silent retreat?
  • If you could change your name to anything, what would you pick?
  • If you could bring one person back to the dead for a day, who would it be and what would you do?

Personal Questions to Ask Your Boyfriend

Intimacy is one of the most important parts of a relationship, but sometimes we feel distant from our partners. Reconnect with these intimate questions to ask your boyfriend.

  • What would you change about your childhood? What would you never change about your childhood?
  • Have you ever gotten anyone pregnant? How did you handle it?
  • What is one thing you wish you could change about yourself?
  • Have you ever cheated on anyone? Have you ever been cheated on?
  • What is your biggest regret?
  • Who are you jealous of?
  • What is the biggest misconception people have about you?
  • Have you ever spent the night in jail?
  • Have you ever been to therapy?
  • Have you ever had to break up with a friend?
  • Are you friends with any of your exes?
  • What bad habit do you have that you would you like to break?
  • Have you ever snooped on a partner?
  • When was the last time you cried?
  • Have you ever had your heart broken?
  • What was the most difficult time in your life?
  • Is it ever okay to lie?
  • What do you like most about yourself?
  • What is the biggest risk you've ever taken?
  • What is the hardest decision you've ever made?

Romantic Questions to Ask Your Boyfriend

Sometimes adding romance to a relationship starts by knowing what question to ask your boyfriend. Reignite your spark with these love questions.

  • Have you ever been in love?
  • Who was your first crush?
  • What was your first kiss like?
  • What is more important in a relationship: an emotional connection or a physical connection?
  • Out of your friends and family, whose relationship do you admire the most?
  • What is the most important quality you look for in a partner?
  • What is the first thing you noticed about me?
  • What is the sexiest thing a partner can wear?
  • What is your ideal date?
  • What couples Halloween costume have you always wanted to do?
  • Would you move to a new city for your partner?
  • Do you keep mementos from past relationships? (Cards, notes, photos, gifts)
  • What is the most ridiculous thing you've ever done to impress someone?
  • Have you ever kissed someone under mistletoe?
  • Do you believe in love at first sight?
  • What is your favorite part about dating?
  • Do you believe in fate?
  • What is the biggest sacrifice you've ever made for a relationship?
  • What is your favorite love song?

Relationship Questions to Ask Your Boyfriend

Communication is an essential part of any relationship. If you don't talk about your relationship and where it's heading, problems may develop over time. These 20 questions to ask your boyfriend will help you both develop the relationship you want.

  • What is your favorite thing about our relationship?
  • What one thing can I do to make our relationship better?
  • Do you like spending time with my family and friends?
  • Do we have enough sex?
  • What do I do that makes you feel appreciated?
  • Are you satisfied with the emotional intimacy that we share?
  • How can we support each other more?
  • Are we changing each other in positive ways?
  • Are we enabling each other's bad habits?
  • What should I do more of? What should I do <em>less </em>of?
  • When we're not together, do we communicate enough?
  • What is your happiest memory from our relationship?
  • What trip would you like to take together?
  • What hobby or skill would you like to learn together?
  • Do you think we fight fair?
  • Do we spend enough time together?
  • What have you always wanted to teach me?
  • What have you always wanted tell me, but never had the guts to?
  • Do I show up in your dreams or fantasies?
  • If we could recreate one day from our relationship, what day would you choose?

Can't get enough? The Nest has 180 questions to ask your girlfriend.

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500 Questions to Ask Your Boyfriend [The Ultimate List]

Embarking on a journey of discovery with your boyfriend can be one of the most exciting aspects of your relationship. Whether it’s to ignite a spark with flirty banter, dive deep into emotional waters, or simply share a laugh over lighthearted and playful queries, the right questions can open up worlds within each other.

This collection of thoughtfully curated questions is designed to help you explore different facets of your boyfriend’s personality, dreams, and desires and to help you both create unforgettable memories and deepen your bond, one question at a time.

Table of Contents

500 Questions You Can Ask Your Boyfriend:

Romantic questions to ask your boyfriend.

Asking your boyfriend these questions can help you find out more about what makes his heart beat a little faster. Whether you’re looking to create a closer connection or just want to hear about the things that light up his world, these romantic questions are sure to bring you closer and sprinkle a little more love into your relationship.

  • What was your first thought when you met me?
  • How do you feel when we’re apart?
  • What does love mean to you?
  • How do you see our future together?
  • What is your favorite memory of us?
  • How do you know when you’re in love?
  • What part of our relationship makes you feel most fulfilled?
  • How can I make you feel more loved?
  • What song makes you think of me?
  • How important is romance in a relationship for you?
  • What little things do I do that you adore?
  • Do you believe in soulmates, and if so, do you think we are?
  • What is your favorite way to spend time with me?
  • How do you feel about public displays of affection?
  • What does a perfect date look like to you?
  • What’s something romantic you’ve always wanted to do?
  • How do you want to be shown love?
  • How did our first kiss make you feel?
  • If you could describe our relationship in one word, what would it be?
  • What adventure would you love to take me on?
  • What are the little things I do that make you smile?
  • How does it feel to hold me in your arms?
  • What aspect of our relationship brings you the most happiness?
  • How do we complement each other?
  • What about our relationship gives you the warmest feelings?
  • How has our relationship changed you?
  • What do you see when you close your eyes and think of us together?
  • Can you recall the moment you realized you were in love with me?
  • What makes our relationship unique to you?
  • How do you think our love has grown over time?
  • What is your favorite thing about our love story?
  • What about me made you fall in love?
  • In what ways do you feel we connect deeply?
  • How do you envision our life together in ten years?
  • How would you describe the way you love me?
  • What loving gesture do you cherish the most from me?
  • What moment with me took your breath away?
  • What word comes to mind when you think about my love?
  • How do you feel when I tell you “ I love you ”?
  • What would a letter filled with your love for me say?
  • How do you balance the need for space with the desire to be close?
  • What gesture of love do you find incredibly meaningful?
  • How do I make you feel secure in our love?
  • What shared dreams do you want us to achieve?
  • Which of our anniversaries has been most special to you?
  • What does a forever with me look like to you?
  • How do you think our lives have been intertwined?
  • What word best describes the love we share?
  • Is there something I do that makes you feel especially loved?
  • How do our hearts speak to each other without words?

Deep Questions to Ask Your Boyfriend

Getting to the heart of what makes your boyfriend tick can create a stronger connection than ever before. With these deep questions, you’ll go beyond the surface and explore the thoughts and feelings that shape who he is. You might find out about his dreams, his worries, or what he finds meaningful in life. It’s a chance for you both to open up and share what’s really going on inside.

  • What life experiences have shaped you the most?
  • What has been your greatest challenge, and how did you overcome it?
  • What are your most profound beliefs about life?
  • Do you have any regrets, and what have they taught you?
  • In moments of self-doubt, how do you lift yourself up?
  • How do you define happiness, and are you there yet?
  • What life lesson took you the longest to learn?
  • How has your perspective on the world changed over the years?
  • What are some dreams you’ve had to let go of, and why?
  • How do you handle loss and grief?
  • What do you think happens after we die?
  • When have you felt the most vulnerable, and what did that teach you?
  • What’s an unpopular opinion you have, and why do you hold it?
  • What values are most important to you in life?
  • In what ways do you want to grow, and how can I support you?
  • What does forgiveness mean to you, and is it easy for you to forgive?
  • What obstacles are you currently facing, and how can I help?
  • Do you believe in fate or that we create our own destiny?
  • What’s the most significant risk you’ve ever taken?
  • What are your thoughts on spirituality?
  • How do you reconcile with parts of your past?
  • What do you fear the most in life?
  • How important is personal growth to you in a relationship?
  • Have you ever had your heart broken, and how did it change you?
  • What parts of life remain a mystery to you?
  • How do you deal with unexpected changes or challenges?
  • What’s a tough decision you’ve had to make recently?
  • What philosophical questions do you ponder the most?
  • How do you find peace in chaotic moments?
  • What are the non-negotiables in your life?
  • How do you think love evolves over time?
  • Can you tell me about a time when you had to rely on your inner strength?
  • What ethical dilemmas have you faced?
  • What aspects of life do you find most fulfilling?
  • How do you balance the need for security with the desire for freedom?
  • What’s been a moment of significant personal growth for you?
  • In what ways do you challenge yourself?
  • What do you most want to achieve in life?
  • How do you manage stress and negativity?
  • What are your thoughts on the concept of soulmates?
  • How do you approach making difficult decisions?
  • What brings meaning to your life outside of our relationship?
  • What’s something you’re still learning about yourself?
  • How do you define success, and do you feel successful?
  • What’s something you’re afraid to tell me but you think I should know?
  • How do you reconcile with the impermanence of life?
  • What’s a pivotal moment in your life that led to personal transformation?
  • How do you feel about vulnerability in our relationship?
  • What aspect of your personality do you think I’m still unaware of?
  • How does the concept of legacy influence your actions and choices?

Serious Questions to Ask Your Boyfriend

Life isn’t all fun and games, and sometimes you need to tackle the big stuff head-on. These serious questions will help you and your boyfriend discuss the things that really matter – like your future, your goals, and what steps you’re both taking to get there. Having these talks can help make sure you’re both on the same page and build a solid foundation for whatever comes your way.

  • What are your thoughts on financial planning and saving for the future?
  • How do you envision your career progressing over the next ten years?
  • What’s your stance on starting a family, and what does that look like to you?
  • How do you approach conflict resolution in a relationship?
  • What are your deal-breakers in a relationship?
  • How do you feel about the role of in-laws in our life?
  • In what way do you think communication is vital in our relationship?
  • What’s your take on maintaining individuality within a partnership?
  • How do you feel about the idea of marriage?
  • Where do you stand on the topic of children and parenting styles?
  • How do you prioritize health and wellness in your life?
  • What are your long-term financial goals?
  • How do you approach the concept of compromise in a relationship?
  • What are your expectations of me as your partner?
  • How do you see us handling major life crises together?
  • What are your biggest concerns about the future?
  • How do you define trust, and how can we strengthen it in our relationship?
  • What’s your philosophy on work-life balance?
  • How do we address differences in core values or beliefs?
  • What steps do you take to secure our relationship?
  • How important is privacy to you within our relationship?
  • What’s your approach to setting and respecting boundaries?
  • How do you feel about seeking external help, like therapy, if we need it?
  • What’s your attitude towards debt and taking loans?
  • How do you handle jealousy or insecurity within our relationship?
  • How would you react if one of us had to move for work?
  • What is your approach to problem-solving as a couple?
  • How do we ensure we maintain equality in our relationship?
  • What is your perspective on the role of tradition in our lives?
  • How would you feel about supporting each other through serious health issues?
  • What role does forgiveness play in our relationship?
  • How do we keep our relationship strong during difficult times?
  • What sacrifices are you willing to make for the sake of our relationship?
  • How do you view the balance of power in a relationship?
  • What measures do you think are essential to future-proof our relationship?
  • How do we maintain respect for one another during disagreements?
  • How do you handle stress within the relationship?
  • What are your thoughts on monogamy and commitment?
  • How do you approach the division of chores and responsibilities at home?
  • How seriously do you take the vows of a marriage?
  • What’s your view on seeking advice from others about our relationship problems?
  • How do we deal with external pressures in our relationship?
  • What would you do if our relationship faced a serious betrayal?
  • How do we balance our relationship goals with personal ones?
  • How do we manage our time together versus time apart?
  • What are your thoughts on changing for a partner?
  • How do we address each other’s mental health needs?
  • What role does sacrifice play in love for you?
  • What are your thoughts on cultural and religious differences in a relationship?
  • How do you think we should handle financial decisions together?

Fun Questions to Ask Your Boyfriend

These fun questions are all about sparking giggles, making silly faces, and enjoying each other’s playful side. Pull these out on a lazy Sunday afternoon or during a dinner date when you both need a little pick-me-up. They’re perfect for lightening the mood and reminding each other how good it feels just to enjoy the simple, fun moments in life.

  • If you could have any superpower, what would it be and why?
  • What’s the most ridiculous outfit you’d wear for a theme party?
  • If we were in a food fight, what would be your ammunition of choice?
  • Which character from a TV show do you envision yourself as?
  • What’s your go-to karaoke song, and can we sing it as a duet?
  • If you could instantly learn any instrument, what would it be?
  • What’s the funniest prank you’ve ever pulled off?
  • If you could spend a day as an animal, which one would you choose?
  • What’s the most useless talent you have?
  • If you could live inside a video game for a day, which one would you pick?
  • What’s the most bizarre dream you’ve had?
  • If we were a superhero duo, what would be our names and powers?
  • What’s the most embarrassing thing you’ve done on a dare?
  • If you found a genie, what would your three wishes be?
  • What board game do you dominate every time you play?
  • If you could swap lives with a historical figure for a week, who would it be?
  • Which reality TV show do you think we’d win as a couple?
  • What’s the funniest joke you know by heart?
  • If you could have a theme song play whenever you enter a room, what would it be?
  • What’s the most childish thing you still enjoy doing?
  • If you could create your own planet, what would it be like?
  • What’s your favorite cheesy pick-up line, and has it ever worked?
  • If you were a wrestler, what would be your entrance theme song?
  • Which cartoon character’s life would you like to live for a day?
  • What’s the wackiest event you’d like us to attend?
  • If you had a time machine, would you go back in time or into the future?
  • What’s the silliest fear you have?
  • What made-up sport would you be an international champion in?
  • If you could be friends with a mythical creature, which would you choose?
  • What’s the funniest thing you’ve seen someone do in public?
  • What would you do during a zombie apocalypse?
  • Which movie would you like to be trapped in for a day?
  • What’s the strangest food combination you enjoy?
  • What’s your favorite bad joke that makes you laugh every time?
  • What’s the weirdest thing a guest has done at your house?
  • What’s the funniest nickname you’ve ever gotten?
  • If your life was a movie, which actor would play you?
  • What’s the most amusing gift you’ve ever received?
  • If we were a band, what would be our name and genre?
  • What’s a ridiculous fact you know that comes up surprisingly often?
  • What’s something wild you’ve always wanted to try but never have?
  • If you could talk to animals, which species would you chat with first?
  • What’s a funny habit you have that few people know about?
  • If you were to perform in a circus, what would your act be?
  • What’s the most outlandish thing you would do if you won the lottery?
  • If we could teleport anywhere right now, where would we go?
  • What’s something that makes you laugh no matter how many times you see it?
  • If you could have an unlimited supply of one thing for the rest of your life, what would it be?
  • What’s the funniest misinterpretation you’ve had of a song lyric?
  • If you were a master inventor, what wacky invention would you create?

Cute Questions to Ask Your Boyfriend

Cute questions are like those snapshots that capture the warmth and fondness you feel for each other. They are the little winks across the room, the nose-boops, and the inside jokes. These questions will help you share the sweetness and create even more adorable memories together.

  • What nickname do you think suits me the most?
  • If we were animals, what would we be?
  • What’s the sweetest thing you’ve ever done for someone?
  • If our love story was a fairy tale, how would you want it to go?
  • What’s your favorite memory of us that makes you smile?
  • If I were a dessert, what would I be and why?
  • What’s the cutest thing you’ve ever seen?
  • How do you feel when you see a message from me pop up on your phone?
  • If we had a pet together, what would you like to name it?
  • What’s the first thing you think of when you hear my name?
  • Which emoji reminds you of me?
  • How would you describe the way I smell?
  • What’s your vision of a perfect day for us?
  • What little things do I do that warm your heart?
  • If you could dedicate a song to our relationship, which one would it be?
  • What small gesture from me means a lot to you?
  • When did you realize you were starting to fall for me?
  • What’s your favorite thing that we do together?
  • Can you describe the moment when you felt most loved by me?
  • What’s the best compliment you’ve ever received from me?
  • If we were to be featured in a cartoon, what would our characters look like?
  • What’s the silliest face I make that you adore?
  • How do you cheer me up when I’m feeling down?
  • What’s your favorite photo of us and why?
  • What’s your go-to thought for when you need to feel happy?
  • If you were to describe our relationship with a movie title, what would it be?
  • What movie scene always reminds you of us?
  • How do you feel when we hold hands?
  • What’s something I say that always makes you laugh?
  • If you were to write a diary entry about our last date, what would it say?
  • What’s a habit of mine that you find endearing?
  • What’s the most heartwarming message I’ve sent you?
  • What simple thing can I do to brighten your day?
  • If we built a fort, what’s the one thing inside it that would make it perfect?
  • How do you imagine us growing old together?
  • What little rituals do we have that you cherish?
  • What’s a cute inside joke between us?
  • How do you feel when we dance together?
  • What would be the title of our love story?
  • What’s something you think we should do together that we haven’t done yet?
  • What’s a quirk of mine that you couldn’t live without?
  • If you could plan the perfect surprise for me, what would it be?
  • How do we make everyday activities romantic?
  • What’s the funniest thing I’ve whispered in your ear?
  • How did you know I was ‘ the one ‘?
  • What moment between us do you think back to when you’re happy?
  • What’s the first thing you noticed about me?
  • What’s the cutest habit we have as a couple?
  • If you could whisk me away to anywhere in this moment, where would we go?
  • How do you feel when you catch me looking at you?

Flirty Questions to Ask Your Boyfriend

Flirting with your boyfriend isn’t just for the early days of dating; it keeps the excitement buzzing between you two. These flirty questions are like a game of catch with little winks and smiles, keeping the energy lively and the air charged with that thrilling connection. 

  • What’s something I wear that you find irresistible?
  • How do you feel when you catch me staring at you?
  • What’s your favorite feature of mine?
  • What’s your favorite time of day to be with me?
  • If we were alone right now, what would you do to me?
  • How does it feel when I whisper in your ear?
  • What’s a fantasy you’ve had about us?
  • How did you feel the first time we held hands?
  • If we were in a crowded room, how would you let me know you’re thinking of me?
  • What’s the most flirtatious thing you’ve ever said to me?
  • What’s a question you’ve been too shy to ask me?
  • How do you want me to kiss you?
  • Where’s your favorite place to be kissed?
  • What outfit of yours do I look best in?
  • If I was a dessert, what would I be and why?
  • What’s one thing I do that makes your heart race?
  • What’s your favorite thing I’ve ever done for you?
  • How do you feel when we hug?
  • When was the moment you realized you were attracted to me?
  • What’s your favorite way to show me affection?
  • What’s a romantic thing you’ve always wanted to try?
  • How do you feel about holding hands in public?
  • What’s the most daring place you’d want to kiss me?
  • If you could choose any nickname for me, what would it be?
  • What’s a secret spot on your body that you love being touched?
  • What’s something flirty you want to whisper to me right now?
  • What’s your favorite memory of a kiss we shared?
  • How do you feel about love bites?
  • What’s a dream date you wish we could go on?
  • If you could pick one word to describe our chemistry, what would it be?
  • What’s the boldest move you’ve ever made on me?
  • If we were the last two people on Earth, how would you make our days special?
  • Do you have a favorite pet name for me?
  • What’s your favorite way to receive a compliment from me?
  • How do you feel about spontaneous kisses?
  • If we had a whole day to ourselves, how would you want to spend it?
  • What’s the most memorable thing we’ve done together?
  • If I dared you to do something right now, what would you want it to be?
  • What’s something you’ve seen me do that you thought was sexy?
  • What’s your favorite way to get closer to me?
  • How do you feel when I play with your hair?
  • What’s a playful thing you love when we do it together?
  • What’s your reaction when I send you flirty texts?
  • How do you describe the way I make you feel to your friends?
  • If we could kiss under the stars anywhere in the world, where would it be?
  • What’s a song that always makes you think of me in a flirty way?
  • How do you feel after a goodnight kiss?
  • What’s something risqué you’ve always wanted to suggest to me?
  • How do you feel when I call you by a flirty nickname?
  • What’s one thing about our relationship that you find incredibly enticing?

Spicy Questions to Ask Your Boyfriend

When you’re looking to shake things up a bit, spicy questions are the way to go. They bring a dash of adventure and an edge of excitement to your conversations. With these fiery prompts, you can explore the steamier paths of your relationship, discover hidden desires, and maybe even ignite new passions.

  • What’s a fantasy of yours we haven’t explored yet?
  • In what outfit do you think I look the most tempting?
  • What’s your favorite way to tease me?
  • Is there a side of you I haven’t seen in the bedroom yet?
  • What’s the most exhilarating place you’ve imagined us being intimate?
  • What’s your favorite thing to hear when we’re together and alone?
  • How do you feel about role-playing?
  • What’s something new you’d like to try with me?
  • Is there a particular scent or perfume that turns you on?
  • What’s the naughtiest thought you’ve had about me recently?
  • What’s a secret turn-on of yours?
  • How do you like to be seduced?
  • What’s your favorite memory of us getting intimate?
  • What’s one thing I do that drives you wild?
  • How do you feel about lingerie?
  • What are your thoughts on public displays of affection?
  • How do you feel about a little biting or scratching?
  • What’s your favorite time of day to be intimate?
  • What part of foreplay do you think I excel at?
  • How would you describe the way we connect physically?
  • What’s a risqué place you’d want to take me?
  • What’s your ideal way to spend a night with me?
  • In what ways do you like to take control in the bedroom?
  • How do you feel about massage oils and candles?
  • If you could pick any song to make love to, what would it be?
  • What’s the most thrilling thing I’ve whispered in your ear?
  • What’s your stance on dirty talk?
  • Is there a movie scene that makes you think of us?
  • How do you react when I give you a sultry look?
  • What do you find most irresistible about me?
  • What’s the sexiest dream you’ve ever had about me?
  • Do you have a preference for what I wear to bed?
  • How do you like to unwind with me after a long day?
  • What’s the most passionate moment we’ve shared?
  • If you could choose one place where we could make love without consequences, where would it be?
  • How do you feel about quickies?
  • In what way do you like to surprise me in intimate moments?
  • What’s the hottest thing about spontaneous intimacy?
  • What’s an intimate act you want more of in our relationship?
  • How do you feel when I take the lead?
  • What’s something in the bedroom you’re curious to try?
  • How does it make you feel when I’m vocal about my pleasure?
  • What’s your favorite way to initiate a steamy night?
  • What intimate gesture do you find incredibly sexy?
  • How do you feel about experimenting with different locations?
  • What’s the most enticing look I’ve given you?
  • Is there a specific type of touch that sends shivers down your spine?
  • What’s your favorite thing to do during cuddle sessions?
  • How do you like to be enticed into the mood?
  • What’s a line from a movie or book that you find sensually inspiring?

Juicy Questions to Ask Your Boyfriend

Juicy questions are the ones that get you both saying, “ Oh, tell me more! ” They’re the questions that reveal the fun secrets, the unexpected confessions, and the tidbits that make for delicious conversation. Whether it’s a bit of gossip, a wild story from the past, or something a little naughty, get ready to share and enjoy the juicy details.

  • Have you ever had a secret that you kept from me, and what was it?
  • What’s the most daring thing you’ve done that I don’t know about?
  • If you could have a hall pass for a celebrity, who would it be?
  • What’s the juiciest piece of gossip you’ve heard recently?
  • What’s something about your past that you think I should know?
  • Have you ever gotten away with something you shouldn’t have?
  • What’s the boldest lie you’ve ever told?
  • Is there something you’ve always wanted to tell me but never had the chance?
  • Have you ever been caught doing something you shouldn’t have?
  • What’s an outrageous thing you desire that you’re hesitant to ask for?
  • What’s your guilty pleasure that almost no one knows about?
  • Have you ever spied on someone, and what did you find out?
  • What’s the juiciest rumor you’ve ever started?
  • Do you have a wild confession to make about your love life before me?
  • Have you ever done something in the heat of the moment that you regretted later?
  • What’s the most scandalous message you’ve ever received or sent?
  • How do you really feel about your friends’ significant others?
  • Have you ever been tempted to snoop through my phone or email?
  • What’s one thing that could totally shock me about your past?
  • What’s the juiciest story you have from a night out?
  • Have you ever been involved in a love triangle?
  • What’s something rebellious you did as a teenager?
  • What’s the most awkward situation you’ve been in with someone I know?
  • What’s a secret hobby or activity you do when no one’s around?
  • Have you ever had a close call that really rattled you?
  • What’s something you’ve lied to your parents about?
  • What’s the craziest thing you’ve done to get someone’s attention?
  • If you could erase one past experience from your life, what would it be?
  • What’s the most thrilling thing you’ve ever witnessed?
  • Have you ever received a gift from someone that had a hidden meaning?
  • What’s an impulsive decision you made that you still wonder about?
  • What’s a question you’ve been dying to ask me but never found the right moment for?
  • Have you ever had a prediction or gut feeling that turned out to be eerily accurate?
  • What’s the biggest risk you’ve taken in a relationship?
  • What’s something about your personality that you keep hidden from most people?
  • Have you ever been involved in a situation that felt like it was straight out of a movie?
  • What’s one thing you swore to never tell anyone, but you’d consider telling me?
  • What’s the most bizarre situation you’ve found yourself in while traveling?
  • Have you ever experienced something supernatural or unexplainable?
  • What’s a piece of advice you ignored that you wish you hadn’t?
  • Have you ever made a decision based on a dream or sign?
  • What’s the juiciest piece of personal news you’ve ever shared with someone?
  • What’s something that excites you but also scares you?
  • Do you have a suspicion or theory about someone we know that you’ve kept to yourself?
  • What’s a wild event from history that you wish you could have witnessed?
  • What’s something you’ve done that you would never want your coworkers to find out about?
  • Have you ever discovered something about someone that completely changed your opinion of them?
  • What’s a mischievous thought you’ve had about someone else’s property?
  • Have you ever been mistaken for someone else and went along with it?
  • What’s the most outrageous request someone has ever made of you?

Random Questions to Ask Your Boyfriend

Tossing a bunch of random questions into the mix is like sprinkling a handful of confetti on your day – unexpected, colorful, and sure to make you both smile. These questions come out of nowhere, keep things fresh, and have the power to turn any regular moment into a fun and quirky adventure. Get ready for surprise answers, bursts of laughter, and some truly unique conversations that’ll give you even more reasons to adore each other.

  • If you could have dinner with any three people from history, who would they be?
  • What’s the most bizarre item you’ve ever bought on impulse?
  • How would you survive a zombie apocalypse?
  • If you could teleport anywhere in the world right now, where would it be?
  • What’s the strangest dream you’ve ever had?
  • If you could bring any fictional character into our world, who would it be?
  • What’s an unusual skill you’d love to master?
  • Which era of history would you have loved to experience?
  • If you could instantly become an expert in something, what would it be?
  • What’s your weirdest habit that you’ve never told anyone?
  • If you could choose any name for yourself, what would it be?
  • Do you believe in any superstitions or omens?
  • What’s a question you’ve never asked me but have always wanted to?
  • If you could choose an alternate reality, which one would you pick?
  • What’s the most random thing you’ve ever witnessed in public?
  • If you could become a character in a game, which would it be?
  • What’s the oddest compliment you’ve ever received?
  • If you could invent a holiday, what would it celebrate?
  • What’s the craziest conspiracy theory you think might be true?
  • If you could have witnessed any event in history, which would it be?
  • What’s the most random piece of trivia you know?
  • If you could have any animal as your protector, which would it be?
  • What’s something that everyone looks silly doing?
  • If you could swap lives with one of your friends for a day, who would it be?
  • What’s the most bizarre thing you’ve ever eaten?
  • If you could communicate with any species, which would you choose?
  • What’s the most random thing that makes you happy?
  • If you found out you had a secret admirer, what would you do?
  • What’s a random act of kindness you’ve never forgotten?
  • If you could have a theme song for your life, what would it be?
  • What’s the most random thing you’re afraid of?
  • If you could design your own planet, what would it look like?
  • What would you do if you won the lottery tomorrow?
  • If you could ask your future self one question, what would it be?
  • What’s the most spontaneous thing you’ve ever done?
  • If you could change one law, what would it be and why?
  • What’s the most random present you’ve ever received?
  • If you could relive a day from your childhood, which would it be?
  • What’s the weirdest tradition you’ve ever heard of?
  • If you could switch places with a celebrity for a day, who would it be?
  • What’s an unusual fear you have that you haven’t told anyone?
  • If you could create a new invention, what problem would it solve?
  • What’s the most random thing that triggers a memory for you?
  • If you had to use a fake name, what name would you make up?
  • What’s the most unexpected turn your life has taken?
  • If you could erase one event from history, what would it be?
  • What’s the most random fact you’ve learned from social media?
  • If you could become an expert in any obscure field, what would it be?
  • What’s the weirdest dream goal you have?
  • If a movie was made about your life, what genre would it be, and who would play you?

Interesting Questions to Ask Your Boyfriend

Interesting questions are the fuel for conversations that can last all night. They’re about the world around us, the mysteries of life, and those “ I’ve never thought of that before ” moments. Asking these questions can lead to deep discussions, fascinating revelations, and a greater understanding of how your boyfriend sees the world.

  • If you could have one historical figure as a mentor, who would it be?
  • What invention do you think will change the future of humanity the most?
  • If you could gain knowledge from any one person’s experiences, whose would you choose?
  • What mystery of the universe do you find most intriguing?
  • Can you think of a movie plot that hasn’t been done yet, but should be?
  • What’s one event from the past that you wish you could have witnessed firsthand?
  • If you could have any artist, dead or alive, create your portrait, who would it be?
  • What’s a skill or craft you admire in others and would like to learn?
  • If you could add one subject to high school curriculums, what would it be?
  • What unsolved mystery would you love to know the answer to?
  • What’s a piece of technology that has significantly impacted your life?
  • If you could explore any planet, which one would you choose?
  • What’s an age-old tradition that you think should be brought back?
  • What historical era do you think you’d fit into seamlessly?
  • If you could have dinner with any fictional character, who would it be?
  • What’s a topic you never get tired of discussing?
  • If you could master a style of dance overnight, which style would you choose?
  • What’s one thing about space exploration that fascinates you the most?
  • What’s an idea or invention you’ve had that you wish you could make a reality?
  • What’s the most interesting documentary you’ve ever watched?
  • If you could interview a famous leader, what questions would you ask?
  • What’s the most valuable lesson you’ve learned from a stranger?
  • What period of art history do you find the most interesting?
  • What’s a philosophy or theory that impacts how you live your life?
  • If you could witness any event in the next 100 years, what would you hope to see?
  • What’s the most interesting book you’ve ever read?
  • Which scientific discovery has the most profound meaning, in your opinion?
  • If you could redesign society from scratch, what would it look like?
  • What concept from a Sci-Fi book or movie do you wish was real?
  • What’s the most creative solution you’ve come up with for a problem?
  • If there was a museum of your life, what would be in it?
  • What’s the most interesting cultural practice you’ve learned about?
  • If you could swap minds with anyone for a day, who would you choose?
  • What’s an area of modern life that you think will be dramatically different in 50 years?
  • What breakthrough in medicine would you most like to see?
  • If you could have a conversation with an animal, which animal would you choose and why?
  • What’s the most interesting natural phenomenon you’ve witnessed or want to witness?
  • If you could decode one secret of the natural world, what would it be?
  • What do you think is the most interesting paradox?
  • If you could learn the absolute truth to one question, what question would you ask?
  • Which underrated historical figure do you think deserves more recognition?
  • If time travel becomes possible, where and when would you travel to first?
  • What’s the most uniquely beautiful location you’ve heard about?
  • What ancient civilization do you find the most compelling?
  • If you could have the answer to any unsolved crime, which would you choose?
  • What’s the most interesting thing you know about the human brain?
  • If you had the opportunity, would you want to know the future?
  • What’s a profession from the past that you find interesting or admirable?
  • What’s the most complex subject that you find intriguing?
  • If you could master any instrument instantly, which would you choose and why?

Frequently Asked Questions

How can i ask my boyfriend romantic questions without being too cliché.

Authenticity is Key: Choose questions that are meaningful to your relationship and phrase them in a way that feels natural. It’s less about being original and more about being sincere and curious.

What if my boyfriend doesn’t ask me questions back?

Encourage Reciprocity: Sometimes, people need prompts. You can nudge the conversation by saying, “ I’d love to hear your thoughts on this too, ” or “ What about you? “

Final Thoughts

Asking your boyfriend these questions isn’t just about getting to know him better—it’s about growing together. Whether you’re looking for a laugh, some romance, or a deep talk, each question is a new chance to connect.

Listen to his answers, share your own stories, and enjoy all the little moments that pop up along the way. It’s these conversations that can bring you both closer and make your relationship even stronger.

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90+ Flirty, Intimate & Personal Questions for Your Boyfriend

Last Updated: July 26, 2023 Fact Checked

This article was co-authored by Lauren Sanders and by wikiHow staff writer, Glenn Carreau . Lauren Sanders is a Professional Matchmaker, Dating Coach, and the Founder of Dating for the Soul. With over four years of experience, she specializes in helping singles find love. Lauren is also the author of Lipstick Faith: A Collection of Inspirational Writings and Life Lessons, You Deserve the World, Rainbows and Strawberries: 100 Devotions for the Brighter Side of Life, and Let's Go Outside Mommy. Lauren holds BS from Dillard University and a Masters from The University of North Georgia. This article has been fact-checked, ensuring the accuracy of any cited facts and confirming the authority of its sources. This article has been viewed 50,537 times.

You’ve got an amazing boyfriend, and things are going great, but there’s so much more you want to know about him! Asking fun and juicy personal questions is certainly a great way to get to know him better, which is why we’ve outlined all the juiciest topics to cover with your boyfriend. Read on for a long and detailed list full of example questions to get you started, from playful questions about his interests to flirty (and downright naughty) questions that’ll add a little spice to your relationship.

“When did you laugh the hardest?”

Playful questions are the perfect start to a lighthearted conversation.

  • “Are you a morning person or a night person?”
  • “What was your first concert?”
  • “Do you believe in aliens or UFOs?”
  • “Did you ever sleep with stuffed animals?”
  • “If you won the lottery, where would you travel and why?”
  • “Who would play you in a movie about your life?”
  • “Are there any unsolved mysteries that interest you?”
  • “If you could pick a theme song for yourself, what would it be?”

“What musician is your guilty pleasure?”

Get the scoop on all of your boyfriend’s interests and favorite things.

  • “What’s your comfort movie?”
  • “What's your go-to karaoke song?”
  • “What’s your favorite take-out food?”
  • “What's your favorite holiday (and holiday food)?”
  • “What’s your favorite board game?”
  • “What hobby do you feel you’re best at?”
  • “Who’s your celebrity crush?”

“What’s your favorite love song?”

Sweet and thoughtful questions are sure to get your boyfriend’s attention.

  • “What's a hobby you think we should try together?”
  • “Do you prefer fancy or casual date nights?”
  • “What's your favorite memory of us?”
  • “What was the last dream you remember having?”
  • “Do you believe in soulmates?”
  • “Have you ever kissed someone under mistletoe?”
  • “If you could have three wishes from me, what would they be?”
  • “What's something you're passionate about that you never get to discuss?”

“What’s your best pickup line?”

Flirty questions can help maintain the spark between the two of you.

  • “Do you remember what I wore on our first date?”
  • “What gives you butterflies?”
  • “How often do you think about me?”
  • “What was our first kiss like for you?”
  • “What types of compliments do you like to hear?”
  • “How do you think I should describe you to other people?”
  • “Have you ever been skinny-dipping?”

“What’s your dirtiest fantasy?”

Turn up the heat with spicy questions for your boyfriend.

  • “What’s the kinkiest thing you’ve ever done?”
  • “Do you ever fantasize about me?”
  • “What positions have you always wanted to try with me?”
  • “Can you guess what color underwear I’m wearing?”
  • “Have you ever taken a bubble bath with someone?”
  • “If you could touch me in one place, where would it be?”
  • “What kind of foreplay do you like?”
  • “What time of day are you most aroused?”

“What was the first thing you noticed about me?”

Questions about attraction may reveal more about his preferences.

  • “What's your favorite physical feature of mine?”
  • “What is your biggest turn-on?”
  • “What qualities make me special to you?”
  • “What color should I wear more?”
  • “How do you describe me to other people?”
  • “What type of scent do you like on a person?”
  • “What’s something you think is true about me, but you've never asked to confirm?”
  • “What do I do that makes you laugh?”

“Have you ever been in love before?”

Juicy questions about your guy’s past can help you get to know him.

  • “What were you thinking on our first date?”
  • “When you were a kid, what career did you want to have?”
  • “How many past partners have you had?”
  • “What was your childhood like?”
  • “Have you ever been cheated on by a partner before?”
  • “What were you looking for when you found me?”
  • “What's the hardest decision you've ever had to make?”
  • “Did you debate whether or not to ask me out?”

“Do you remember your dreams?”

Surprise him with a random, quirky question he’s never heard before.

  • “If you started a podcast, what topic would it be about?”
  • “What's a hidden talent you have that you never get to show off?”
  • “Do you ever feel like you lived a past life?”
  • “What's one fact no one else knows about you?”
  • “What do you think your best attribute as a boyfriend is?”
  • “Do you sing in the shower?”
  • “What's the craziest dare you've ever accepted during Truth or Dare?”

“What makes you feel fulfilled?”

Deeper questions can help you build emotional intimacy.

  • “What's the biggest misconception people have about you?”
  • “What's your biggest fear? Do you think you could face it?”
  • “How would you define success?”
  • “Are you proud of your accomplishments thus far?”
  • “What gets you out of bed in the morning?”
  • “What's the biggest risk you've ever taken?”
  • “Do you believe in second chances?”
  • “What scares or worries you the most about relationships?”

“What’s your love language?”

Strengthen the relationship by learning how he expresses his love.

  • “How do you like to show love?”
  • “How do you want me to show love to you?”
  • “What can each of us do to improve our relationship?”
  • “Do I make you feel valued?”
  • “When did you know you were in love with me?”
  • “Do I make you feel heard?”
  • “What's your favorite thing about our relationship?”
  • It may be very helpful for both of you to find your love languages and discuss them together, since the concept of “love languages” defines different ways to give and show love.

“What’s your definition of intimacy?”

Questions about intimacy can help you understand each other’s desires.

  • “Are you satisfied in the bedroom?”
  • “Do you think we spend enough time together?”
  • “Do you think we have healthy emotional intimacy?”
  • “Is there anything we haven't tried that you'd like to?”
  • “Do you wish I was more affectionate?”
  • “Is our relationship physical enough for you?”
  • “How many times do you think couples should have sex a week?”
  • “What's your favorite type of kiss?”

“Where do you see our relationship heading?”

Serious questions about the future can determine long-term compatibility.

  • “What are your job or career goals?”
  • “What kind of memories would you like to make with me?”
  • “Where do you see this relationship in the next 5 years?”
  • “What goals do you have for us?”
  • “What’s your opinion on marriage and children?”
  • “How do you imagine a day in the life of us married with kids?”
  • “Do you ever worry about us breaking up? How can I help you feel better?”

Expert Q&A

Lauren Sanders

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Expert Interview

travel questions to ask your boyfriend

Thanks for reading our article! If you’d like to learn more about dating, check out our in-depth interview with Lauren Sanders .

  • ↑ https://thepleasantrelationship.com/questions-for-couples/
  • ↑ https://www.scienceofpeople.com/questions-to-ask-your-boyfriend/
  • ↑ https://www.betterhelp.com/advice/relations/how-well-do-you-know-me-questions-25-questions-for-couples/

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Lauren Sanders

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50 Romantic Questions to Ask Your Boyfriend for a Deeper Connection

50 Romantic Questions to Ask Your Boyfriend for a Deeper Connection

Romantic questions to ask your boyfriend conversation starters relationships. In any relationship, keeping the flame of romance alive is essential.

One way to do this is by engaging in meaningful conversations that deepen your connection and understanding of each other. 

Asking romantic questions not only helps you learn more about your boyfriend but also strengthens the emotional bond between you two.

155 Engaging Questions to Get to Know Someone Deeply

So, if you’re looking to spice up your relationship or simply want to get to know your partner on a deeper level, here are 50 romantic questions to ask your boyfriend:

50 Romantic Questions to Ask Your Boyfriend

Content Summery

  • What is your fondest childhood memory?
  • If you could travel anywhere in the world with me, where would it be and why?
  • What’s your idea of a perfect date night?
  • What do you think is the most romantic thing you’ve ever done for someone?
  • What’s your love language, and how can I show you love in that way?
  • If you could relive one moment with me, what would it be?
  • What qualities drew you to me when we first met?
  • What’s the most romantic gesture you’ve ever received?
  • How do you envision our future together?
  • What’s your favorite thing about our relationship?
  • What’s something you’ve always wanted to do but haven’t yet?
  • How do you feel loved and appreciated?
  • What’s your favorite memory of us together?
  • If you could change one thing about our relationship, what would it be?
  • What’s your idea of the perfect lazy Sunday together?
  • What’s the most meaningful gift you’ve ever received?
  • What’s one thing you want to accomplish in your life, and how can I support you?
  • What’s your favorite way to unwind after a long day?
  • If you could write a love letter to your future self, what would you say?
  • What’s the most adventurous thing you’ve ever done?
  • What’s your favorite physical feature about yourself, and why?
  • What’s your idea of the perfect romantic getaway?
  • What’s your ultimate relationship goal?
  • If you could only keep one memory of us, what would it be?
  • What’s your definition of true love?

Romantic Questions to Ask Your Boyfriend Conversation Starters

  • What’s your favorite thing about being in a relationship?
  • What’s your idea of the perfect surprise date?
  • What’s something you’ve learned about yourself from being in a relationship?
  • What’s one thing you’ve always wanted to tell me but haven’t yet?
  • What’s your favorite love song, and why does it resonate with you?
  • What’s your biggest fear when it comes to love and relationships?
  • What’s one thing you admire about me?
  • What’s your idea of the perfect anniversary celebration?
  • What’s the most romantic movie you’ve ever watched, and why?
  • What’s your dream proposal scenario?
  • What’s one thing you wish people knew about you?
  • What’s your idea of the perfect way to spend a rainy day together?
  • What’s your favorite thing about our relationship dynamic?
  • What’s your favorite memory of us laughing together?
  • What’s one thing you’ve always wanted to learn about love?
  • What’s your favorite thing about our intimacy?
  • What’s your idea of the perfect way to express gratitude in a relationship?
  • What’s one thing you’ve learned from past relationships that you apply to ours?
  • What’s your favorite thing about our communication style?
  • What’s one thing you want us to do together in the future?
  • What’s your idea of the perfect way to show affection?
  • What’s one thing you want to accomplish as a couple?
  • What’s your favorite romantic tradition we have?
  • What’s one thing you want me to know about your love for me?
  • What’s your idea of the perfect way to end each day together?

Asking these romantic questions can open up avenues for deeper conversations and strengthen the emotional connection between you and your boyfriend.

Remember, the key to a lasting and fulfilling relationship is communication, understanding, and appreciation for each other’s thoughts and feelings.

So, take the time to ask these questions and enjoy the journey of discovering more about your partner’s heart and soul.

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Relationships

600 questions to ask your boyfriend that will bring you closer.

travel questions to ask your boyfriend

Relationships tend to get boring when both partners stop working, believing love is enough to steady their ship. While love can indeed strengthen the fabrics of your relationship, if it is not constantly fueled, it can lead to a gradual disconnect and eventual fallout.

To forestall the chances of this ever occurring in your affair, you need to take active steps to bolster the love and unity you share with your partner. One of such steps is through romantic, inquisitive, and deep questions.

There are numerous questions to ask your boyfriend to get him to open up to you about aspects of his life, his family, and your relationship together which you hitherto had no knowledge of. Remember that men are often complicated.

As such, these questions to ask your boyfriend must be carefully constructed to avoid giving a wrong impression of interrogation or fault-finding.

travel questions to ask your boyfriend

The reason we recommend these questions to ask your boyfriend is because when handled right, they can boost the intimacy and fervor in your relationship to levels you have never experienced.

These questions to ask your boyfriend revolve around romantic, cute, deep, and juicy issues that would capture his imagination and get him thinking seriously about the relationship.

If you are in a long-distance relationship, it is encouraged that you take these questions with utmost importance as they provide a great opportunity to spice up your relationship and fix yourself permanently in the heart of your man.

So, without further ado, let’s get into the list of fascinating questions to ask your boyfriend. Ready for the ride? Let’s go!

Romantic Questions To Ask Your Boyfriend When You Are Bored

travel questions to ask your boyfriend

This list of romantic questions to ask your boyfriend are the best you would find anywhere. When you have been in a relationship for a while and have talked about pretty much everything, you might find yourself getting bored.

These questions can help you connect with your partner; you will get to know them on a deeper romantic level.

1.  What does your dream wedding look like?

2.  What is your idea of a romantic honeymoon destination?

3.  How many kids do you want to have?

4.  What do you want to do on Valentine’s day?

5.  What did you think when you first saw me?

6.  Do you believe in soulmates?

7.  Would you do a time capsule for our grandkids?

8.  What is your idea of the perfect date?

9.  How would you define love?

10.  What is a relationship deal-breaker for you?

travel questions to ask your boyfriend

11.  What does your ideal retirement look like?

12.  What is your favorite thing about our relationship?

13.  What made you fall for me?

14.  Which of my nicknames for you is your favorite?

15.  How did our first kiss make you feel?

16.  Is there such a thing as being too much in love?

17.  What is your idea of the perfect romantic gift?

18.  What’s the most romantic movie you’ve ever seen?

19.  What is one thing I do that you will never get tired of?

travel questions to ask your boyfriend

20.  What is your favorite memory of us?

21.  What turns you on the most?

22.  Do I make you happy?

23.  How can I be a better woman for you?

24.  Are anniversaries important to you?

25.  What is your biggest fear in this relationship?

26.  What would be the perfect gift for you?

27.  If the world was going to end tomorrow, how would you make our last day together memorable?

28.  If you found out that I am pregnant right now, how would you react?

29.  If you could choose one romantic movie for us to star in, which would it be?

30.  Would you kiss me if people were around?

31.  If I had to move halfway across the world, would you come with me?

travel questions to ask your boyfriend

32.  If the house was on fire, what three things would you save?

31.  If I could only make you one meal for the rest of your life, what would it be?

32.  If we won the lottery, what would we do with the money?

33.  Would you still love me if I looked different?

34.  If you could correct one of my flaws, what would you fix?

35.  What three words would you use to describe me or our relationship?

36.  Guess what I like about you the most?

37.  How much do you think I love you?

38.  Do you prefer a passionate kiss or a long warm hug?

39.  What’s the most sensual dream you’ve ever had?

40.  Do you like hearing how beautiful you are?

travel questions to ask your boyfriend

41.  Guess what I like about you most.

42.  How do you like a girl to show her feelings?

43.  Describe making love in three adjectives.

44.  What’s your favorite thing about making love?

45.  What do you remember most about the night/day we first met?

46.  What about our relationship makes you really happy?

47.  How long did you think our relationship would last when we first started dating?

48.  If you had one word to describe our love what would it be?

49.  Do you believe there’s one person you’re meant to be with?

50.  Do you believe in fate? destiny?

51.  What’s one difference between us that you absolutely love?

travel questions to ask your boyfriend

52.  What is the hottest thing a partner can wear?

53.  Do you believe in love at first sight?

54.  What is your favorite love song?

55.  What’s one similarity between us that you absolutely love?

56.  What about me made you fall in love?

57.  Is love something that scares you?

58.  What about love scares you?

59.  What’s your favorite memory of us?

60.  What sound do you love?

61.  What are your favorite scents?

62.  What is your favorite karaoke song?

63.  What is your favorite thing to do on a rainy day?

travel questions to ask your boyfriend

64.  What’s one thing you want to do together that we’ve never done before?

65.  If something happened where I had to move very far away, would you attempt long-distance? Or go our separate ways?

66.  Where is your favorite place to be with me?

67.  What’s one thing you’re scared to ask me, but really want to know the answer to?

68.  What’s one thing you feel our relationship is lacking?

69.  What’s your favorite non-physical quality about me?

70.  What’s your favorite physical quality about me?

71.  If our relationship ended, what’s the one thing about it you’d miss the most?

travel questions to ask your boyfriend

72.  Do you think you’ve been vulnerable in our relationship?

73.  What do you think was your most vulnerable moment in our relationship?

74.  What do you think has been the hands-down funniest moment since we started dating?

75.  What’s one quality about me that I see as a flaw that you absolutely love?

76.  What’s one secret you’ve wanted to tell me, but haven’t?

77.  Do you think there’s such thing as the ‘right’ person for you?

78.  Do you think I’m the ‘right’ person for you? (If yes) What about me makes me the ‘right’ person?

79.  What fictional character do you have a crush on?

80.  Have you ever tried to invent something?

81.  If you could change your name to anything, what would you pick?

travel questions to ask your boyfriend

82.  If I said you could date other people, would you?

83.  What do you think I’d say is your most attractive quality?

84.  What’s your favorite way to show affection?

85.  What’s your favorite way to receive affection?

86.  What’s one thing you think makes our relationship unique from everyone else’s?

87.  If you could change one thing about our relationship what would it be?

88.  If we could go anywhere together right now, where would you want to go?

89.  What do you think is your biggest strength in this relationship?

90.  What’s your biggest weakness in this relationship?

91.  Who do you think is the most affectionate in our relationship?

travel questions to ask your boyfriend

92.  How do you think we both have changed since we first started dating?

93.  What about us both is exactly the same since we first started dating?

94.  What’s one thing I do that makes you feel good, that you wish I did more?

95.  What’s one thing about your life you would never change for someone else, including me?

96.  What about us do you think works well together? How do we balance each other out?

97.  What’s one thing you hope happens in the future of our relationship?

98.  What does love mean to you?

99.  What do I mean to you?

100.  What does this relationship mean to you?

101.  What makes you feel the most loved?

102.  What’s your dream date night?

103.  What’s your favorite romance movie?

104.  What’s your favorite meal to cook for date night?

travel questions to ask your boyfriend

105.  What kind of music puts you in the mood?

106.  What’s the number one thing that you think makes a relationship last?

107.  If I gave you $ 1000 and asked you to get something for us, what would you get?

108.  What cute name would you want to give me?

109.  What do you love most about me?

110.  What setting do you think makes the perfect date night atmosphere?

111.  What physical action or gesture do you find romantic?

112.  Who do you think makes a great example of a relationship and why?

travel questions to ask your boyfriend

113.  What’s your favorite way I touch you?

114.  If you could travel anywhere in the world with me with no monetary restrictions, where would we go?

115.  What song do you think of when you think of me?

116.  Is there anything about me you might not know but want to know?

117.  When and what was the first moment you knew you were in love with me?

118.  What’s your most favorite outfit I wear?

119.  What’s your favorite restaurant for date night?

120.  What could I do to improve our relationship?

121.  What about me first attracted you?

122.  What’s been one of the funniest times we’ve had together?

travel questions to ask your boyfriend

123.  What do you say to others when you talk about me?

124.  Why do you think we met each other?

125.  What do I do that helps you calm down?

126.  Is there anything I can do to help you feel more special?

127.  What’s one thing you want to do with me that we haven’t done yet?

128.  When are you the happiest with me?

129.  What great adventures do you think we’ll achieve in the next 5 years?

130.  What values do you think are most important in a relationship?

131.  Is there anything you’re afraid to accomplish that I can help you with?

132.  Is there anything you’d like me to be willing to change?

travel questions to ask your boyfriend

133.  Has anything surprised you about our relationship?

134.  What can I do to encourage you on a regular basis?

135.  What strengths do you see in our relationship?

136.  What weaknesses do you see in our relationship?

137.  What goals would you like to set for our relationship?

138.  What do you think is most important for communicating in our relationship?

139.  Would you rather receive the most amazing massage you’ve ever had in your entire life from me or have me pour my heart and soul out in the most beautiful poem you’ve ever read?

140.  What moment would you want to relive again and again?

Fun Questions To Ask Your Boyfriend

travel questions to ask your boyfriend

If you want to freshen up your relationship, we have put together a list of fun, enjoyable questions to ask your boyfriend. Every relationship at some point needs some sort of spark.

These questions will offer you and your partner an exciting way to enjoy yourselves while you get to know each other. Choose from the options below to drive your relationship to the next level!

1.  Which celebrity are you rather certain would be your BFF if you ever met?

2.  What’s the longest you’ve ever gone without sleep? …without a shower? …without clean underwear?

3.  What’s your biggest pet peeve?

4.  What is one superpower you would hate having?

5.  What food do you wish you cook like a world-class chef?

6.  What’s the last book you read and really enjoyed?

7.  What is one song that can always pull you out of a bad mood?

8.  What’s the worst movie you’ve ever seen?

9.  What’s something you misunderstood as a child and only realized much later was wrong?

10.  If you had to, what would you change your name to?

travel questions to ask your boyfriend

11.  Which color do you most identify with?

12.  If you were in charge, what holiday would you create?

13.  What fast food place are you ashamed to admit you, love?

14.  What was the strangest thing you ever did as a child?

15.  What’s the funniest lyric you’ve ever misheard?

16.  Which sports team would you rename, and to what would you rename them?

17.  Have you ever been in a stage production?

18.  Which game show do you think you’d definitely win?

19.  Is there a game you’d like to play that we haven’t tried before?

20.  What would you say is your worst trait?

travel questions to ask your boyfriend

21.  What would you say is your best trait?

22.  Can you describe your ideal vacation?

23.  What’s something that scares you?

24.  What is your perfect brunch order?

25.  What’s your Patronus?

26.  Which sandwich topping do you most identify with?

28.  In your childhood, what’s a food that you used to really love that you can’t believe you ate?

29.  What ad is super irritating to you?

30.  If you had to run for public office, what would you run for?

travel questions to ask your boyfriend

31.  What are one or two things you don’t understand about the generation after yours?

32.  What are one or two things you don’t understand about the generation that precedes yours?

33.  If you could only watch one sport and all others were banned for the rest of your life, which sport would you choose?

34.  What are your thoughts on pickled foods that aren’t cucumbers?

35.  Can you name one thing that you know is kind of ridiculous, but you’re adamant about and will argue over it to the death?

36.  Do you have a favorite flower or plant?

37.  What kind of pet would you love to have?

38.  Do you consider yourself a spender or a saver?

39.  What was your dream job when you were a kid?

40.  Are you a mountain person or a beach person?

travel questions to ask your boyfriend

41.  What’s the strangest dream you’ve ever had?

42.  Would you get a tattoo? Or, what’s your plan for your next tattoo?

43.  Which celebrity chef would you want to learn from?

44.  Is there anything that you to do to reduce stress?

45.  What are your three favorite colors?

46.  Do you have any wardrobe accessories you can’t live without?

47.  What’s something you’ve tried that you thought you’d hate but actually ended up liking?

48.  What’s your favorite emoji?

49.  What’s the goofiest knock-knock joke you know?

50.  Choose one and explain your choice: dog, cat, fish, or bird?

travel questions to ask your boyfriend

51.  If you could become a master artist, why type of art would you make?

52.  Which country would you like to visit together?

53.  What’s your favorite thing for me to wear?

54.  What goes on your favorite ice cream sundae?

55.  What piercings would you like to get?

56.  What’s your favorite season?

57.  What’s your favorite seasoning?

58.  What is your dream car?

59.  Did you ever have a favorite childhood toy?

60.  Do you have a preferred kind of noodle for your mac & cheese?

travel questions to ask your boyfriend

61.  What is one thing you’ve done that you’re most proud of?

62.  What’s your favorite dessert?

63.  If you could relive one day of your life, which day would you pick?

65.  Would you rather have photos or paintings hanging the walls of your house/apartment?

66.  Have you ever won a TV or radio contest? If you did, what did you win?

67.  Which social media platform is your favorite?

68.  Which Social Media platform is your least favorite?

70.  Which would you rather watch: The Today Show, Good Morning America, or CBS This Morning?

71.  What’s your favorite spa treatment? Or what kind of spa treatment do you most want to try?

72.  Should people unwrap gifts slowly or quickly?

travel questions to ask your boyfriend

73.  What’s your biggest complaint about the country?

74.  What is one thing you think could make our relationship stronger?

75.  Are there any festivals or events you’d like to go to the next time we’re together?

76.  What’s your favorite thing to see at a circus?

77.  Which amusement park ride would you head for first?

78.  What type of beverage do you drink most in a day?

79.  What’s one skill you’d like to learn or improve?

80.  What are your top five snack foods?

81.  Would you rather read the book than seen the movie, or see the movie and read the book?

82.  What’s the most recent comedy special you’ve seen?

travel questions to ask your boyfriend

83.  Is there a TV show you’re hooked on?

84.  How do you feel about mixing Play-Doh colors?

85.  What’s the longest you’ve ever worn a pair of jeans without washing them?

86.  What’s your preferred cut of underwear?

87.  What was your favorite fairy tale growing up?

88.  For what occasion did you wear the fanciest clothes you’ve ever worn?

89.  If you could meet one person today, living or dead, who would you choose to meet?

90.  What song comes on the radio and makes you feel all the feels?

travel questions to ask your boyfriend

91.  Which holiday is your favorite?

92.  What is your most prized possession?

93.  Crossword, word search, or sudoku?

94.  What is a project you’d like to make with your own hands?

95.  What is one commonly held belief that you just don’t buy into?

96.  What is the most hideous fashion fad that you’ve ever seen?

97.  What’s the first you’re going to do the next time we see each other?

98.  What would you do if you returned from work and found me in the shower?

99.  What game did you love most while growing?

100.  What game would you never try out even if I gave you $100?

Serious Questions To Ask Your Boyfriend

travel questions to ask your boyfriend

One of the ways to test your boyfriend’s intellectual capacity is to ask deep questions. Of course, you don’t want to be with a dummy who is unable to sustain impactful conversations.

Asking your boyfriend serious questions helps you assess his worldview, see topics that stimulate him, as well as learn his views on controversial topics. Here are some suggestions of serious questions to ask your boyfriend.

1.  If you could fix one world problem, what would it be?

2.  If you could live in any era, which would it be and why?

3.  What advice would you give to a person who is just graduating high school?

4.  If you could have chosen your own name, what would you have picked?

5.  If you became famous, would you enjoy the limelight or miss your privacy?

6.  If you had $200 to spend on something special just for me, what would you buy?

7.  If you had three wishes, what would they be?

8.  If you were told you have a terminal illness, how would you take the news?

9.  If you only had a week left to live, what are some things you would do?

10.  Would you sacrifice yourself for a stranger?

11.  If a family member needed a kidney and you were the only match, would you give one up?

travel questions to ask your boyfriend

12.  You suspect that your neighbors may be abusing their child, do you mind your own business or call the police?

13.  If I went missing, my body never recovered, would you move on or devote your life to looking for me? If you did move on, how long would you wait?

14.  If you could invite 3 people to dinner, who would they be?

15.  If you could live till you were 90 and either have the mind or body of a 30-yr-old, which would you choose and why?

16.  If you could wake up tomorrow and have gained one ability, what would it be and why?

17.  If a crystal ball could tell you the truth about your life, me, or the future, what would you want to know?

18.  If you could live anywhere, where would you live?

19.  Which one fits you better? “Live for the moment”, or “Save the best for last”?

20.  What’s your favorite thing about yourself?

21.  If you could change anything about yourself, what would it be?

travel questions to ask your boyfriend

22.  Do you prefer going out or staying in?

23.  Would you consider yourself an externally motivated or internally motivated person?

24.  How do you deal with failure?

25.  Do you put more attention to the people around you or the things around you?

26.  When things break, do you prefer to fix them or replace them?

27.  Would you consider yourself materialistic?

28.  What would you consider a perfect day?

29.  What would be your perfect date night?

30.  What are some things that offend you?

31.  What is one thing that you cannot start your day without?

travel questions to ask your boyfriend

32.  If you’re stressed out, what helps you wind down?

33.  When you die, do you want to be buried or cremated? Why?

34.  What inspires you?

35.  Would you consider yourself an optimist, pessimist, or realist?

36.  We notice an old man living out of a shopping cart behind a grocery store. What is your first thought about him?

37.  Someone calls me something horrible. Do you let me fight my own battles, or jump in and defend me?

38.  Do you think it’s okay to have a close female friend at work?

39.  What are three things you are willing to splurge on for yourself?

travel questions to ask your boyfriend

40.  What’s something that no one else knows about you?

41.  Do you ever rehearse a phone call beforehand?

42.  When did you last sing to yourself? To someone else?

43.  What are you most thankful for?

44.  Is there something you’ve dreamed of doing for a long time? Why haven’t you done it?

45.  What do you most fear about getting older?

46.  Have you ever done something you regretted?

47.  Where do you see yourself in five years?

48.  When was the last time you shed a tear?

49.  What is a tradition you did as a child that you want to do with your kids someday?

travel questions to ask your boyfriend

50.  What are some things in life that you had to learn the hard way?

51.  Do you have any dreams from childhood that you can vividly recall?

52.  What were your childhood aspirations, and how have they changed?

53.  How do you picture your life when you’re 60?

54.  What is your most terrible memory?

55.  How have you changed the most since you were younger?

56.  In what areas do you want to change the most?

57.  When was the first time you were in love?

58.  When was the first time you said I love you?

59.  Is there any book that changed your life?

60.  What is your biggest insecurity?

61.  Is there anything you’re ashamed of?

62.  Is there anything you wouldn’t want your family to know?

63.  If you could change anything about the past, what would it be?

travel questions to ask your boyfriend

64.  Why do you think the divorce rate is so high nowadays?

65.  What do you think is the biggest flaw of the welfare system?

66.  If you were running for president, what are three key things you would include in your campaign?

67.  Are you pro-choice or pro-life?

68.  How do you feel about genetically modified food?

69.  What is one thing that you feel would make any small business owner more successful?

70.  What invention do you think has done the most for the human race?

71.  Should children be allowed to have cell phones?

72.  Do you think a person’s outward appearance says anything about who they are as a person?

travel questions to ask your boyfriend

73.  How important do you think it is to do well in school?

74.  Would you consider yourself proud to live in this country?

75.  Is there anything too serious to be joked about?

76.  What is your position on premarital lovemaking?

77.  What do you look for most in a spouse?

78.  What religious/spiritual views do you have and why?

79.  How important is it for you to save money?

80.  How important is it for you to invest money?

81.  How important do you think making out is in a marriage?

82.  If one of us had to move far away, would you be able to handle a long-distance relationship?

travel questions to ask your boyfriend

83.  What is one thing that can destroy a relationship and never be forgiven?

84.  Do you want to have kids someday when you meet the right person?

85.  Do you think it’s more important to work or spend time with family?

86.  What are three key elements in every successful relationship?

87.  Do you think people can or should be friends with their exes?

88.  Do you believe emotional ‘cheating’ is just as bad as real cheating?

89.  What do you think of open relationships?

90.  Are you looking for commitment?

91.  What was your first impression of me?

92.  Would you surprise me with an expensive gift, or would you consult me before spending the money on it?

travel questions to ask your boyfriend

93.  Would you rather I be good in the kitchen or good in the bedroom?

94.  What do you think is more admirable, a stay-at-home mom or a career-driven mom?

95.  Would you rather leave a big impact on the world or a big impact in your family?

96.  What song do you think best fits our relationship?

97.  Do you think a proposal should be a grand public display or a private intimate moment?

98.  If we had children, what features would you want them to get from you and which from me?

99.  What’s something you could never compromise about?

100.  Do you forgive and forget or forgive and remember?

101.  If you had kids, what would be your biggest hope and the biggest fear for them?

travel questions to ask your boyfriend

102.  What is one area in your life where you feel like something is missing?

103.  Do you think your significant other can be both your best friend and your lover?

104.  Do you think it’s better to have the worst house in a nice neighborhood or the best house in a bad neighborhood?

105.  Is life anything like you had pictured it would be growing up?

106.  Would you rather have a life full of love or a life full of money?

107.  Can a positive outlook make any situation better?

108.  Do you think children are more of a blessing or a burden?

109.  If I was giving birth to our child and complications arose that meant only one of us would make it, who would you save?

110.  What would you want said about you after you die?

111.  If you could go back in time to give advice to your younger self, what would you say?

Questions To Ask Your Boyfriend To Test His Love

travel questions to ask your boyfriend

How deep does his love for you go? Is there a special person in your life that you want to connect with on a deeper level?

Do you want to see if your boyfriend truly loves you, if he is still trying to find his feet around relationships, or if you are just a phase he is going through? The questions to ask your boyfriend in this section have been specially arranged to give you the answers to these and many more.

1.  What is it that you love about me the most?

2.  If you could change anything about me what would it be?

3.  What color do you think suits me best?

4.  How’s my hair looking today?

5.  Do you prefer me with makeup or looking natural?

6.  Do you remember how we first met?

7.  How did you get me to fall for you?

8.  Did you imagine then… we would be where we are today?

9.  Are you convinced I am the one for you?

10.  Was is it, love, at first sight for you?

travel questions to ask your boyfriend

11.  What is it that makes us work the most do you think?

12.  Do you think we could improve on our love?… If so what do you think it would be?

13.  If there’s one thing you could do for me, or I could do for you what would it be?

14.  On a scale of 1 to 10, how much do you love me?

15.  What make’s our love different to all the rest?

16.  What’s your ideal date? Or would you rather remain indoors with me?

17.  What’s my favorite romantic spot for us?

18.  If could go anywhere.. where would it be?

19.  What’s your favorite food?

20.  Do I like milk in my tea/coffee?

travel questions to ask your boyfriend

21.  Where do you want to take me for dinner this weekend?

22.  Do you think we need to try something new?

23.  Shall we start a hobby together?

24.  Would you like to meet me for a drink after work?

25.  Would you like to watch a movie with me all day?

26.  What’s your ultimate bedroom fantasy?

27.  What’s your favorite form of sensual pleasure?

28.  Is there a feature about me that turns you on straight away?

29.  Where do you like me to kiss you?

30.  Do I like wearing underwear?

travel questions to ask your boyfriend

31.  Where shall we go on our next holiday together?

32.  Do you see yourself spending the rest of your life with me?

34.  Do you want to start a family together one day?

35.  What would you like to accomplish from life?

36.  How are you feeling about our relationship?

37.  Did you think about me at work today?

39.  Do you want me to put some music on?

40.  Would you like me to accompany you to the gym?

travel questions to ask your boyfriend

41.  Would you prefer to read, watch a movie or just be with me?

42.  If you could start a hobby with me, what would it be?

43.  What are you most afraid of happening to us?

44.  What have your other relationships taught you before now?

45.  Would you like me to give you a massage?

46.  Would you like me to make your lunch for work tomorrow?

47.  Would you like me to press your shirts for you?

48.  How deep would you honestly say your love for me goes?

49.  What’s one thing we could change about each other that could help us move forward and understand each other better?

50.  Have you loved another more than me before?

Cute Romantic Questions To Ask Your Boyfriend

travel questions to ask your boyfriend

If you want to bond with him in a way that makes you inseparable forever, I suggest you try these cute questions to ask your boyfriend. You will certainly get to discover aspects of him you never knew about.

1.  Which would you pick between me and a box of gold?

2.  What is the first thing that comes to mind in the morning when you wake up next to me?

3.  Do you miss me when we’re not together?

4.  Would you shout my name to the world from the biggest skyscraper?

5.  Do you think that there is a special reason why we met?

6.  Is there anything about me that inspires you to do things differently?

7.  Is there a song that reminds you of me when you’re listening to it?

8.  How many times did you want to kiss me before our “official” first kiss?

9.  Would you kiss me on the forehead?

10.  Do you find me cute?

11.  If only one cookie remained, would you give it to me?

travel questions to ask your boyfriend

12.  What is the cutest thing about me?

13.  Does it make you feel good when I tell you what a gentleman you are?

14.  How do you feel when I say to you: ‘I love you‘?

15.  Do you find me pretty?

16.  Do you think I look cute even when wearing tomboy outfits?

17.  Do you really mean it when you say you love me?

18.  Do you have a pet name for me?

19.  What’s something I do (that I don’t realize I do) that you love?

20.  What is a silly thing about me that you love?

travel questions to ask your boyfriend

21.  Would you ever write a poem/story about me?

22.  Do you still get butterflies when we’re kissing?

23.  How do you feel when I send you a text message?

24.  Have you ever daydreamed about me?

25.  What is your favorite dream that involved me?

26.  Do I inspire you to become the best version of yourself?

27.  Do I look cute while being mad at you?

28.  If we are watching a scary movie, can you hug me when I get really scared?

29.  Would you take my hand to dance, even if we were the only ones on the dance floor?

30.  Is there any flower that reminds you of me?

travel questions to ask your boyfriend

31.  Would you ever want to lie on the grass and watch the stars with me?

32.  What outfits do you like the most on me?

33.  When you’re alone, do you ever imagine that I’m there next to you?

34.  What’s the craziest thing you would do for me?

35.  Has our relationship influenced you to change in any way? How?

36.  Has been with me helped you learn about yourself more?

37.  Do you like the feeling of falling in love with me?

38.  What is the one thing you’re really dying to do with me? Or one experience you would like to share with me?

39.  What is your favorite thing about us as a couple?

40.  What is your favorite color to see on me?

travel questions to ask your boyfriend

41.  When did you first realize that I like you?

42.  Could you imagine your life without me in it?

43.  Did you find winning me over to be hard or not? How so?

44.  What is the best compliment you have ever received from me?

45.  How many times did you think about inviting me on a date before you actually invited me?

46.  How would you describe me in one paragraph?

47.  What is your favorite nickname of mine?

48.  What do you consider to be the most irresistible part of a woman?

49.  Can I call you when I feel like hearing your voice?

50.  Do you trust me with your whole heart?

travel questions to ask your boyfriend

51.  Does it make you smile when I send you a text message?

52.  Would you stay in a long-distance relationship with me if we had no other choice?

53.  Would you meet my family?

54.  If you could describe my personality in 5 words, what would they be?

55.  How would you describe the feeling of being in a relationship with me?

56.  Is there anything that you don’t like about me?

57.  Do you see yourself with me in the future?

58.  Did anyone give you advice on how to ask me out on our first date?

59.  How do you feel about holding my hand in public?

60.  Would you kiss me when we’re in public?

travel questions to ask your boyfriend

61.  If I was scared, would you hold my hand?

62.  Do you find me the kind of girl you’d take home to your parents?

63.  How do you feel when I touch your body/face?

64.  Do you like when I massage you?

65.  Where is your favorite place to chill with me?

66.  Would you take a break for one week from your favorite hobby to spend it with me?

67.  Would you introduce me to your family?

68.  What is your ideal type of movie to watch with me?

69.  Have you ever been in love before me?

70.  When did you decide you wanted to introduce me to your friends?

travel questions to ask your boyfriend

71.  What are the traits of a healthy relationship?

72.  What did you enjoy about being single that you would like to keep in our relationship?

73.  Is there anything you would like to change about us as a couple?

74.  Is there anything you’re afraid to tell me?

75.  Is there anything you would want to know about me, but you’re afraid to ask?

76.  What was your overall first impression of me when you first saw me?

77.  Do you remember some of the details of our first date?

78.  Which do you prefer more—kissing in the dark, under the Sun or in the rain?

79.  What is your favorite place for making love?

80.  Do you like to cuddle?

81.  Would you rather hug me for 6 seconds or kiss me for 2 seconds?

travel questions to ask your boyfriend

82.  Are you happy with me?

83.  Were you nervous/anxious before our first kiss?

84.  When did you decide you wanted us to be officially together?

85.  Are there any flaws that you like about me?

86.  How does your ideal date look?

87.  What is the best part about being in a relationship and why?

88.  Do you ever talk about me when you’re spending time with your friends?

89.  If one of your friends or family members told you to break up with me because he/she didn’t like me, would you?

90.  Would you be embarrassed if I called you by a cute name in front of your male friends?

travel questions to ask your boyfriend

91.  If you caught another guy flirting with me, what would you do or say?

92.  Do you prefer a date watching Netflix and chill alone, or going out at the movie theater?

93.  Do you think your friends and family (will) like me, too?

94.  Where would you want to go on vacation with me and why?

95.  Would you rather go on a road trip with me or with your friends?

96.  What is your definition of an ideal partner, and do I possess any of those traits?

97.  Have you ever been deeply hurt or disappointed in someone?

98.  Do you feel relaxed with me?

99.  What’s your biggest fear for this relationship?

100.  What’s your biggest deal-breaker during a date?

travel questions to ask your boyfriend

101.  What is your favorite memory so far of spending time with me?

102.  When did you fall in love with me?

103.  When did you first realize you loved me?

104.  Do you remember the day of our first date?

105.  Would you ever write a romantic love song for me?

106.  If I were to make you breakfast in bed, what would you want it to be?

107.  Would you ever risk your life in order to save mine?

108.  Do you believe some people are destined to be together?

109.  How would you describe our first kiss/love making?

110.  What is your favorite romantic place ever?

travel questions to ask your boyfriend

111.  Do you think we’re soulmates?

112.  What are the 3 reasons you like/love me?

113.  Do you believe that love can conquer anything?

114.  Would you carry me in your arms if my feet hurt?

115.  Are we both lovers and best friends?

116.  If we could spend our next weekend anywhere we want, where would it be?

117.  Would you prepare a romantic dinner for me, and if so, what would it look like?

118.  How do you show your love to someone you care about the most?

119.  What is the one thing that you like about me the most?

120.  If you had only 2 minutes with me, what would you want to do?

travel questions to ask your boyfriend

121.  What does it feel like to you when we’re lying next to each other?

122.  What are you usually thinking about when we’re kissing?

123.  What is your favorite body part of mine?

124.  Where do you like to kiss me the most?

125.  Where is your favorite place to be kissed?

126.  How does it feel to kiss me on the wrist?

127.  Do you like kissing me on the neck?

128.  What is the first thing that comes to mind when I’m calling you?

129.  What do you enjoy more – cuddling or kissing with me?

130.  Do you like seeing me in dresses?

travel questions to ask your boyfriend

131.  Would you notice that I want to make love to you without me telling you so?

132.  What’s something that will make me fall in love with you instantly?

133.  What will you do if I suddenly kissed you right now, right here?

134.  Aside from being hot all day, what do you do for a living?

135.  What do you wear to bed (if anything at all) when you sleep?

136.  What would you do if you woke up and suddenly found me lying on your bed next to you?

137.  What kind of underwear do you think I’m wearing right now?

138.  What was the happiest moment of your life to now?

139.  What helps you persist when you feel like giving up on something?

140.  Do you like reading romantic poems?

141.  What are 3 situations that can always make you cry?

travel questions to ask your boyfriend

142.  Do you have a secret that you haven’t told anyone before?

143.  Have you ever cried while watching a sad movie?

144.  When did you have your first kiss?

145.  Do you have a celebrity crush?

146.  When do you feel respected the most?

147.  What is something you’re nostalgic about?

148.  Do you like meeting new people?

149.  What is the stupidest thing you’ve ever done?

150.  What is the best gift you’ve received for your birthday?

Conclusion As much as you love asking your boyfriend some serious questions to find out what he’s all about, a long list of deep questions might be draining.

This is why I recommend mixing up the serious questions with some fun and juicy ones to keep things light and interesting. Also, ensure you set the mood for the session so that it doesn’t turn out tedious instead of exciting.

Save this for later!

travel questions to ask your boyfriend

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LoveToKnow

70+ Intimate Questions to Ask Your Partner for a Deeper Bond

When people hear the word "intimate," they often think that it only relates to bedroom conversation, but intimate questions can cover a much wider spectrum. They can concern anything from your childhood dreams to how your partner pictures your future together. You can learn juicy new details about one another and strengthen your bond by sharing parts of yourselves.

There are lots of intimate questions to ask your lover about an array of topics. Find out how they might describe you to someone else, their favorite ways to express love, what they might like to change in your relationship, and lots more. These questions are just the beginning of meaningful conversations that will bring you closer together.

How to Ask Intimate Questions to Build Your Bond

How you ask a question matters almost as much as what you ask. Set the right tone with these tips:

  • Don't just spring the question your partner. Instead, make it part of a conversation.
  • Create a routine where you and your partner each choose a question off the list to ask one another. You can do this regularly.
  • If you're hoping to ask your partner a really juicy question, be prepared to reveal something too. Intimacy comes from both people being vulnerable.
  • Find a quiet time when you won't be interrupted. Deep conversations require some privacy.

According to The Gottman Institute , some of the key ways to help build intimacy in a relationship are to connect emotionally, increase intimate communication, show appreciation, and be vulnerable with one another. Asking your partner meaningful questions is one way to do these things and may help you connect with your partner and build your relationship.

General Attraction Questions to Ask Your Partner

There are some things that you just want to know, even though they can't be confined to a single category. These are the things about preferences, how you talk about one another to others, and maybe even a wish or two thrown into the mix of questions to ask your girlfriend, boyfriend, or partner.

  • What is the first thing you noticed about me?
  • What role does physical attraction play in whether or not you pursue a relationship?
  • What type of scent do you like on a person?
  • Would you say you have a "type"? Do I fit what you thought you were looking for?
  • How do you describe me to other people?
  • How do you think I should describe you to other people?
  • What could I do for you that I don't do now?
  • What is the first thing you think when you see me?
  • What qualities make me special to you?
  • Do you look at other men (women)?
  • If you could have three wishes from me, what would they be?
  • What goals do you have for us?
  • What was the first thing you thought when you met me?
  • How would you respond if my appearance drastically changed, either overnight (new haircut and different hair color, for example) or over time (more/less muscle, weight gain/loss)?
  • What is something you think is true about me, but you've never asked to confirm?
  • How big of a deal are special occasions for you?

Deep Questions for Couples to Build Emotional Intimacy

Building your emotional connection often involves choosing to be vulnerable with one another. We're talking really taking a risk here. Share your fears and worries and put yourself out there in a way that risks rejection. It can pay off big time in emotional intimacy if you're vulnerable like that.

  • What were you afraid of as a kid? What are you afraid of now?
  • Do you ever worry about us breaking up? How can I help you feel better?
  • What kinds of things make your heart skip a beat? Am I one?
  • What do you worry about at night?
  • What was the last dream you had about me?
  • In what ways are you still a child inside?
  • What's something you haven't told me because you're afraid I might judge it?
  • How do you think being hurt has made you more or less willing to be vulnerable in a relationship?
  • What part of yourself do you not love but need me to love?
  • How can I make you feel emotionally safe?
  • What's the first thing you remember as a kid? How did you feel in that memory?

Questions About the Past

Before you can move forward with your partner, you want to know about their past. If you're planning to be intimate or stay together for a long time (maybe even get married ), you should feel comfortable asking anything you feel you should know or whatever you're curious about. Remember, asking these questions will open the gate to your past as well.

  • Have you ever cheated on a partner? If not, have you considered it but changed your mind?
  • How many past partners have you had?
  • Did you debate whether or not to ask me out? Why would you have chosen not to?
  • What were you thinking on our first date?
  • Have you ever been in love before me? Will you tell me about that person if you have?
  • Who is your role model in life? Who is your role model in love?
  • What did it feel like when you realized you were in love with me?
  • Do you think we were so destined to be together, that if we hadn't decided to date when we did and lost touch, we'd run into each other again? Or do you think meeting was luck?
  • What were you looking for when you found me? Were you looking for love at all?

Serious Questions About the Future

Want to know if you and your lover are compatible long-term? Ask the hard questions about where things are going. Go as far into the future as you feel like you should, but keep the current length of your relationship in mind (and the plans you've already discussed). After all, you don't want to ask about things like financial planning for retirement if you've only been dating a few weeks, or you may give the wrong impression.

  • Where do you see this relationship headed in the next year? What about the next five years?
  • What is your opinion on marriage and children?
  • Would you stay with me if you found out I was unable to bear children? How would this affect us?
  • What are your job or career goals, and how could they affect our relationship?
  • Where do you see yourself living when you retire?
  • I want to be a good lover, and I want to be there for you. What can I do for you to be that person?
  • How do you imagine a day in the life of us married with kids? What about a week in the life?
  • What are your thoughts on having our elderly parents live with us if they can't live on their own one day?
  • How do you plan to save for retirement? What are your goals?
  • What kind of memories would you like to make with me?

Intimate Questions About Love

People express love in so many different ways; it's important to get a good understanding of what will speak to your partner's heart. You also probably have questions for your potential mate about their thoughts and feelings (past and present) on love.

  • What can I do to show you how much I love you?
  • Do you believe in soulmates? What about love at first sight?
  • Have you ever been hurt in the past and questioned the possibility of love?
  • When did you realize you were in love with me?
  • Do you see our love lasting? Do you ever have any doubts?
  • If you had to choose, would you rather receive a gift or have someone do something nice or helpful for you?
  • Do you like sentimental gifts or do you always want a gift to have a practical purpose and be something you need?
  • How do you think you best express love?
  • What types of compliments do you like to hear ?

Juicy Questions for Couples About Intimacy

Intimacy is an important part of any serious relationship. It's not all about what goes on in the bedroom, but it's a big deal. There are things you can do outside of the bedroom or nights you can plan based on your significant other's fantasies, and asking a few juicy questions can help you learn these details. Don't be shy. If you want to know something and build intimacy, just ask.

  • Is our relationship physical enough for you? What would make it better in your eyes?
  • How and where do you like to be touched? Are there any places I don't know about?
  • Do you have any fantasies you would like fulfilled?
  • What are your thoughts on toys?
  • Is there anything we haven't tried that you'd like to?
  • Ideally (and a bit realistically, too), how often would you like for us to be intimate?
  • What are some things I can do outside of the bedroom to keep the feelings of intimacy going all day?
  • Would you like me to be more or less assertive in the bedroom?
  • What kind of fantasies did you have before you met me?
  • How can I make you feel seen and accepted when we're intimate together?
  • What is something about your intimate history you've never told anyone before?

Intimate Text Questions to Ask Your Partner

Texting is a major form of communication for many couples, so it's no surprise that intimate conversation can happen via text (we're not just talking sexting either). It might even be easier to ask intimate questions via text if you're someone who becomes embarrassed with intimate conversation when face-to-face. Try some of these text questions to initiate some intimate conversation.

  • What do you miss most about me right now?
  • What's something you've always wanted to say to me but couldn't?
  • What would you like me to do the next time we're together?
  • Where would you like me to kiss you?
  • What is the closest you've ever felt to me?
  • What one word would you like to be the theme of our relationship?
  • How can I be a better partner to you?
Need to Know When you pose an intimate question for your partner, you need to be open to listening. You may get an answer you are surprised by or don't want to hear. It's important not to judge your partner. If you find yourself upset or surprised, take a moment to digest what your partner has told you before responding. Remember, the two of you are not going to agree on everything.

Choose What You Want to Know

Open communication is often the key to lasting love. Keep in mind your partner may want to ask you intimate questions in return, so be ready to answer them. Relationships are give-and-take, after all. If you need to lighten the mood after opening up to one another, try a few random yes or no questions for a laugh. And if you'd like to get inspired with even more questions, there are some things to ask your girlfriend that could also be adapted for any partner.

Happy couple laughing and talking at kitchen table

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  3. 200+ Funny Questions to Ask Your Boyfriend

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  6. Five Questions To Ask Yourself Before Solo Traveling on lexeats.com

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