180 Questions to Ask Your Boyfriend

Boyfriend gives girlfriend flowers
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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

Couple embrace outside during winter

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.


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


Cute Questions to Ask Your Boyfriend

Gay couple walk along the Santa Monica pier

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.


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


Fun Questions to Ask Your Boyfriend

Couple laughs while moving boxes

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.


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


Dirty Questions to Ask Your Boyfriend

Couple kissing in bed

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.


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


Good Questions to Ask Your Boyfriend

Couple laughs while eating dinner

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.


  1. 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?
  2. What do you want to do when you retire?
  3. What is your ideal vacation? Staying at an all-inclusive resort in Maui, sightseeing in London, or camping at Yosemite National Park?
  4. What is your favorite city?
  5. If you could have any skill without having to work for it, what would it be?
  6. Do you think it's possible for men and women to just be friends?
  7. How do you like to be treated when you're sick? Do you like to be waited on hand and foot or left alone?
  8. Do you have any phobias? (Spiders, heights, germs, etc.)
  9. What is your biggest pet peeve?
  10. What cause have you volunteered for that you feel passionately about?
  11. If you were going to start a charity, what would it be for?
  12. Do you watch, read, or listen to the news?
  13. What is the best advice anyone ever gave you?
  14. Do you like talking on the phone?
  15. What are your relationship deal breakers?
  16. What relationship cliché do you think is true?
  17. If you had to go back to school, what would you study?
  18. What is your favorite time of year?
  19. What motivates you?
  20. What has been the best year of your life so far?


Random Questions to Ask Your Boyfriend

Happy couple running on the beach

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.


  1. What fictional character do you have a crush on?
  2. Do you believe in ghosts?
  3. Have you ever pranked anyone? Have you ever been pranked?
  4. If you could eat only three foods for the rest of your life, what three would you choose?
  5. If you could trade places with one person for a day, who would it be?
  6. What is your hidden talent?
  7. Do you ever feel like you had a past life?
  8. Have you ever broken any bones?
  9. If you were going to get a tattoo today, what would it be of?
  10. If you could inhabit any movie, TV show, book, or other fictional universe, where would you live?
  11. Do you collect anything?
  12. What is your theme song?
  13. If you could wake up tomorrow and be fluent in any language, what language would you choose?
  14. Do you have any superstitions?
  15. If you could go back to any moment in your life and do things differently, would you?
  16. Have you ever been skydiving?
  17. Have you ever tried to invent something?
  18. Would you ever go on a silent retreat?
  19. If you could change your name to anything, what would you pick?
  20. 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

Boyfriend and girlfriend smile in bed

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.


  1. What would you change about your childhood? What would you never change about your childhood?
  2. Have you ever gotten anyone pregnant? How did you handle it?
  3. What is one thing you wish you could change about yourself?
  4. Have you ever cheated on anyone? Have you ever been cheated on?
  5. What is your biggest regret?
  6. Who are you jealous of?
  7. What is the biggest misconception people have about you?
  8. Have you ever spent the night in jail?
  9. Have you ever been to therapy?
  10. Have you ever had to “break up" with a friend?
  11. Are you friends with any of your exes?
  12. What bad habit do you have that you would you like to break?
  13. Have you ever snooped on a partner?
  14. When was the last time you cried?
  15. Have you ever had your heart broken?
  16. What was the most difficult time in your life?
  17. Is it ever okay to lie?
  18. What do you like most about yourself?
  19. What is the biggest risk you've ever taken?
  20. What is the hardest decision you've ever made?


Romantic Questions to Ask Your Boyfriend

Boyfriend and girlfriend making a heart with their hands

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


  1. Have you ever been in love?
  2. Who was your first crush?
  3. What was your first kiss like?
  4. What is more important in a relationship: an emotional connection or a physical connection?
  5. Out of your friends and family, whose relationship do you admire the most?
  6. What is the most important quality you look for in a partner?
  7. What is the first thing you noticed about me?
  8. What is the sexiest thing a partner can wear?
  9. What is your ideal date?
  10. What couples Halloween costume have you always wanted to do?
  11. Would you move to a new city for your partner?
  12. Do you keep mementos from past relationships? (Cards, notes, photos, gifts)
  13. What is the most ridiculous thing you've ever done to impress someone?
  14. Have you ever kissed someone under mistletoe?
  15. Do you believe in love at first sight?
  16. What is your favorite part about dating?
  17. Do you believe in fate?
  18. What is the biggest sacrifice you've ever made for a relationship?
  19. What is your favorite love song?
  20. Would you rather spend the night cuddling by the fire after a day of skiing, or go dancing at a nightclub after a day of laying on the beach?


Relationship Questions to Ask Your Boyfriend

Gay couple watch TV in bed

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.


  1. What is your favorite thing about our relationship?
  2. What one thing can I do to make our relationship better?
  3. Do you like spending time with my family and friends?
  4. Do we have enough sex?
  5. What do I do that makes you feel appreciated?
  6. Are you satisfied with the emotional intimacy that we share?
  7. How can we support each other more?
  8. Are we changing each other in positive ways?
  9. Are we enabling each other's bad habits?
  10. What should I do more of? What should I do less of?
  11. When we're not together, do we communicate enough?
  12. What is your happiest memory from our relationship?
  13. What trip would you like to take together?
  14. What hobby or skill would you like to learn together?
  15. Do you think we fight fair?
  16. Do we spend enough time together?
  17. What have you always wanted to teach me?
  18. What have you always wanted tell me, but never had the guts to?
  19. Do I show up in your dreams or fantasies?
  20. 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.