280 Questions to Ask Your Boyfriend to Spark a Conversation

What deep questions can I ask my boyfriend to understand him better?
on May 29, 2024
Read time: 10 mins

“Would you love me if I was a worm?” 

There are certain things you ask your boyfriend that are meant to be silly, but what are the questions to ask your boyfriend that really deepen your connection? 

When you’re in a relationship, you should never run out of things to talk about, as there is always something new to learn about your loved one! From conversation starters to deep questions, we’re always inventing new ways to inspire connection between our couples. 

If you’re stumped with what to ask your boyfriend (or girlfriend!) next — we’ve got you covered with this bumper pack of questions to keep the conversation flowing! 

How can I deepen my conversation with my boyfriend?

Getting to know your partner on a deeper level is what a relationship is all about. 

Research shows that healthy communication plays a huge role in relationship satisfaction, with meaningful conversations key to your growth as a couple. 

Even though you might talk every day, sometimes having some different questions or conversations up your sleeve can inspire a deeper connection. For example, our Paired daily questions inspire couples to dive into topics they may never have discussed before — sparking new ideas and topics you never touched on! 

What are some questions to ask your boyfriend? 

If sparking new and exciting conversations with your partner sounds right up your alley, we’ve got all the right questions to get you started. 

Are you looking to dive a little deeper? Or do you want some random questions to just get your boyfriend talking? From deep to devilish, these are the questions to ask your boyfriend to keep you talking for hours! 

Deep questions to ask your boyfriend 

  1. What is your proudest moment to date?

  2. Who is your best friend?

  3. What is your favorite memory together? 

  4. What’s your favorite thing about yourself? 

  5. What is your favorite memory of someone who has passed away? 

  6. If you had to live with one person for the rest of your life, who would you choose? 

  7. In what ways do you think we’re different? 

  8. Or, in what ways do you feel like we’re the same? 

  9. What makes you smile even when you’ve had the worst day? 

  10. Tell me something that you’ve never told anyone else. 

  11. What’s your biggest fear? 

  12. Are you closer to your mom or your dad? 

  13. Would you be friends with your younger self? 

  14. Do you have a biggest fear about our relationship? 

  15. What is your earliest childhood memory? 

  16. What’s your favorite part of being an adult? 

  17. How do you like to unwind after a stressful day?

  18. What’s your favorite way to express love? 

  19. What advice from a family member or friend has stuck with you the most? 

  20. How do you take care of your own mental health? 

  21. What is the role of communication in a healthy relationship for you? 

  22. What’s your favorite way to receive love? (ie. your love language!) 

  23. What do you think are the most important qualities in a healthy relationship? 

  24. When was the last time you cried? 

  25. Has anything ever triggered a change in perspective? 

  26. Do you have a dream job? 

  27. Have you ever seen your parents cry? 

  28. What would a family have to do for you to cut them off? 

  29. Do you consider yourself more of an introvert or extrovert? 

  30. What is one experience that changed your life forever?

  31. What does happiness mean to you?

  32. How do you define success in relationships? 

  33. Do you have a life philosophy? 

  34. Do you think that people can change?

  35. What impact do you want to leave behind on the world? 

  36. How do you prioritize the people you love in your life? 

  37. What’s the biggest life lesson you’d want to pass on to your kids? 

  38. Where do you see yourself ten years from now? 

  39. What aspect of your personality are you most proud of? 

  40. Do you have any self-improvement goals? 

Spicy questions to ask your boyfriend 

  1. If you had to pick one position for the rest of your life, what would it be? 

  2. What’s your favorite part of foreplay? 

  3. What’s your favorite part of my body?

  4. What was I doing the last time you felt turned on by me? 

  5. What is your favorite part of your body to be kissed? 

  6. What is your favorite place for making love? 

  7. Do you prefer to sleep naked? 

  8. What’s the most adventurous thing you’ve done in bed?

  9. Have you ever had a dream about me?

  10. What’s your favorite fantasy?

  11. How do you feel about role-playing?

  12. What’s your favorite way to be touched?

  13. Do you have a favorite lingerie or outfit you’d like to see me in?

  14. What’s the naughtiest thought you’ve ever had about me?

  15. How do you feel about experimenting with new things in bed?

  16. What’s the wildest place you’ve ever had sex?

  17. Do you like talking dirty?

  18. Do you like the idea of sending *those* kinds of photos when we’re apart? 

  19. What’s your opinion on using toys?

  20. How do you feel about sexting?

  21. What’s the sexiest thing someone has ever done for you?

  22. What’s your favorite type of kiss?

  23. How important is physical intimacy to you?

  24. What’s the best sexual experience you’ve ever had?

  25. Do you like being in control or being dominated?

  26. What’s one thing you’ve always wanted to try in bed?

  27. How often do you think about sex?

  28. What’s the most erotic dream you’ve ever had?

  29. How do you feel about public displays of affection?

  30. How do you feel about sexting? 

Juicy questions to ask your boyfriend

  1. What is your guilty pleasure?

  2. Who was your first kiss? 

  3. What’s the worst first date you’ve ever had? 

  4. Do you have a go-to pickup line?

  5. What’s your worst breakup story? 

  6. Can you give up social media? 

  7. Were you nervous during our first kiss?

  8. Would we have been friends or dated if we’d known each other in high school?  

  9. Who is your favorite family member? 

  10. What’s the craziest thing you’ve ever gotten the ‘ick’ from? 

  11. Do you have any relationship dealbreakers? 

  12. What age were you when you had your first relationship? 

  13. When was the last time you felt butterflies? 

  14. How would you describe your first time having sex? 

  15. What’s your biggest pet peeve? 

  16. If you could re-do the day that we met, what pickup line would you use on me? 

  17. How have family members reacted to your previous relationships? 

  18. Have you ever ghosted someone?

  19. What’s the most awkward date you’ve been on?

  20. Do you believe in love at first sight?

  21. How do you feel about open relationships?

  22. What’s your opinion on long-distance relationships?

  23. Have you ever had a crush on a friend’s partner?

  24. What’s the most jealous you’ve ever been in a relationship?

  25. How do you handle conflict in a relationship?

  26. What’s the biggest risk you’ve ever taken in love?

  27. Have you ever lied to get out of a date?

  28. What’s the longest relationship you’ve ever had?

  29. How do you feel about marriage?

  30. What’s the most romantic thing you’ve ever done for someone?

Fun questions to ask your boyfriend 

  1. Do you have any hidden talents?

  2. What fictional character most reminds you of me? 

  3. What’s the wildest thing on your bucket list? 

  4. What’s your bucket list country you want to visit? 

  5. What’s your favorite movie or TV character from childhood? 

  6. What’s your favorite movie theatre snack? 

  7. What were you like in high school? 

  8. What’s your comfort TV show? 

  9. Were you cool in high school? 

  10. What’s your weirdest habit? 

  11. Do you believe in star signs? 

  12. Are there any musicians you’d love to see live for the first time?

  13. What’s one superpower you’d love to have?

  14. What’s your favorite holiday you’ve ever been on? 

  15. What’s your most memorable experience from high school? 

  16. If you could be any fictional character, who would you be? 

  17. If you had to choose only one cuisine forever, what would it be? 

  18. What’s your most embarrassing moment? 

  19. What's the funniest memory that sticks out in your mind?

  20. What’s the worst pick-up line ever? 

  21. What’s your idea of a perfect date night?

  22. What’s the craziest thing you’ve ever done on a dare?  

  23. What’s the cheesiest pickup line you’ve ever used or heard? 

  24. What’s your favorite video game or board game?

  25. If you could have dinner with any three people, dead or alive, who would they be?

  26. What’s your dream car?

  27. What’s the most unusual food you’ve ever tried?

  28. If you could instantly become an expert in something, what would it be?

  29. What’s your favorite childhood memory?

  30. If you were a superhero, what would your name and powers be?

Serious questions to ask your boyfriend 

  1. What’s on your anti-bucket list? Like what things have you tried and never want to do again? 

  2. What is a mistake you’ve made in a past relationship that you don’t want to repeat? 

  3. Have you ever broken up with someone?

  4. How do you feel about women proposing to men? 

  5. Have you ever been tested for STIs?

  6. Do you feel the need to know your significant other’s phone password? 

  7. How is your mental health currently? 

  8. Do you think any personal questions should be off-limits in relationships?

  9. What qualities do you value in a significant other? 

  10. Would you like to emulate the parenting style of your own parents? 

  11. Would you take on a significant other’s religion if they had one? 

  12. Is family important to you? 

  13. Do you consider me as your best friend and partner? Or do you think they should be separate? 

  14. Do you think that you handle stress well? 

  15. What are your thoughts on therapy and counseling?

  16. How do you define cheating in a relationship?

  17. What are your views on financial responsibility and sharing expenses?

  18. How do you feel about having children?

  19. What’s your opinion on prenups?

  20. How do you handle conflict in a relationship?

  21. What are your thoughts on gender roles in a relationship?

  22. How do you see our future together?

  23. What are your career goals?

  24. How important is personal space in a relationship for you?

  25. What’s your stance on adopting pets?

  26. If you had to move for your partner’s job, would you? 

  27. Would you prefer to have a joint bank account? 

  28. How do you approach making big decisions?

  29. What’s your opinion on maintaining friendships with exes?

  30. How do you deal with trust issues?

Random questions to ask your boyfriend 

  1. If you had to eat one food every day for the rest of your life, what would you choose? 

  2. What was your favorite candy as a kid? 

  3. What’s the part of your day that you most look forward to?

  4. Do you think that you’re more of a Ross, Chandler, or Joey? 

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

  6. If you could only wear one color forever, which one would it be?

  7. What’s the last movie or TV show that made you cry?  

  8. Would you ever go on a reality TV show? 

  9. When was the last time you felt energized by your work? 

  10. How many places have you lived? 

  11. What’s your favorite place to have a takeaway from? 

  12. Would you rather always be hot or always cold? 

  13. If you could have any animal as a pet, what would it be?

  14. What’s your favorite board game?

  15. Do you prefer sunrise or sunset?

  16. Do you have a random fact that you like to bring up? 

  17. If you could have any job in the world, what would it be?

  18. What’s your favorite season and why?

  19. If you could live in any time period, when would it be?

  20. Do you have a book that you could re-read over and over? 

  21. If you had to choose coffee or tea, what would it be? 

  22. If you could master any instrument, what would it be?

  23. What’s the best advice you’ve ever received?

  24. What’s the weirdest dream you’ve ever had?

  25. If you could travel anywhere in the world right now, where would you go?

  26. Do you like rainstorms? (When you’re inside!) 

  27. If you could meet any historical figure, who would it be?

  28. What’s your favorite type of cuisine?

  29. Do you prefer cats or dogs?

  30. What’s your favorite kind of dessert?

Cute questions to ask your boyfriend 

  1. What does your perfect day look like?

  2. What’s your favorite thing about me? 

  3. What is your favorite thing about our connection?

  4. How would you describe our first date? 

  5. What’s your favorite part of my personality? 

  6. If you were to use a pick-up line on me right now, what would it be? 

  7. Do you believe in soulmates? 

  8. What’s your favorite pet name for me?

  9. What’s the most romantic thing you’ve ever done?

  10. How do you feel when we’re apart?

  11. What’s your favorite compliment to receive from me?

  12. What’s a song that reminds you of us?

  13. Can you describe the moment you knew you loved me? 

  14. What’s your favorite way to spend a weekend together?

  15. What’s your favorite thing to do with me?

  16. How would you describe our relationship in three words?

  17. What’s your favorite memory of us so far?

  18. What’s something you love that I do for you?

  19. How do you show that you care about me?

  20. What’s your favorite way to be comforted by me?

  21. What’s a dream vacation you’d love to take with me?

  22. What’s a small thing that always makes you think of me?

  23. What’s your favorite inside joke we have?

  24. What’s a hobby you’d love to try together?

  25. What’s your favorite meal that I cook?

  26. How do you feel when I’m happy?

  27. What’s the best surprise you’ve ever received from me?

  28. What’s something that you think is a little bit cringy (but that you secretly love!) 

  29. What’s the moment you knew you wanted to know me on a deeper level? 

  30. What’s a small thing that I do that you find adorable? 

Questions to ask your boyfriend over text

  1. What’s a song lyric that you can’t get out of your head right now?

  2. If you could teleport anywhere right now, where would you go?

  3. What’s the best meme you’ve seen today?

  4. If you could have dinner with one fictional character, who would it be?

  5. What’s something you’re looking forward to this week?

  6. If you could change one thing about today, what would it be?

  7. What’s the funniest thing that’s happened to you recently?

  8. What’s a quote that inspires you?

  9. What’s a movie you can watch over and over again?

  10. If you could swap lives with anyone for a day, who would it be?

  11. What’s the best thing that happened to you this month?

  12. What’s a new skill you’d love to learn?

  13. What’s your favorite way to relax after a long day?

  14. What’s the most interesting thing you’ve read recently?

  15. If you could instantly know any language, what would it be?

  16. What’s your favorite snack to have while watching a movie?

  17. What’s something that always makes you laugh?

  18. What’s the best gift you’ve ever received?

  19. If you could live in any city, where would it be?

  20. What’s your favorite way to spend a rainy day?

  21. What’s a hidden gem in our city that you love?

  22. If you could redo any day in your life, what would it be?

  23. What’s something you wish more people knew about you?

  24. What’s a podcast you’re currently enjoying?

  25. What’s your favorite type of weather?

  26. If you could have any animal as a pet, what would it be?

  27. What’s the most beautiful place you’ve ever visited?

  28. What’s your favorite holiday tradition?

  29. If you could have any superpower, what would it be?

  30. What’s your favorite app on your phone right now? 

Serious questions to ask your boyfriend 

  1. How do you think couples should resolve conflict? 

  2. How do you handle it when you feel unappreciated in a relationship?

  3. How do you feel about open relationships or polyamory?

  4. How do you feel about sharing financial responsibilities in a relationship?

  5. How do you deal with a partner who doesn’t meet your emotional needs?

  6. What’s your stance on prenuptial agreements?

  7. How do you envision our life together in the next five years?

  8. What are your thoughts on marriage and long-term commitment?

  9. How do you handle financial stress and budgeting in a relationship?

  10. How important is personal space and alone time to you in a relationship?

  11. How do you prioritize your career and personal ambitions alongside your relationship?

  12. How do you think we can maintain intimacy and connection over the long term?

  13. What’s your approach to maintaining a work-life balance in a relationship?

  14. What are your expectations around household responsibilities and chores?

  15. How do you deal with feelings of jealousy?

  16. What’s the biggest lie you’ve ever told in a relationship?

  17. How do you balance personal growth and maintaining a relationship?

  18. How do you approach discussions about future plans and goals in a relationship?

  19. What’s your approach to handling disagreements or conflicts with extended family members?

  20. How do you feel about seeking couples therapy or counseling if we encounter serious issues?

  21. What are your core values and how do they influence your decisions and lifestyle?

  22. How do you deal with stress and what support do you expect from your partner during stressful times?

  23. What are your non-negotiables in a relationship?

  24. How do you feel about balancing time spent together and time spent with friends or hobbies?

  25. How do you handle situations where we might need to compromise on our individual goals for the sake of the relationship?

  26. How do you view the importance of physical health and wellness in our relationship?

  27. What are your thoughts on long-distance relationships? Would you be willing to do one with me? 

  28. How would you deal with sexual dissatisfaction in a relationship? 

  29. How do you feel about discussing and setting relationship goals together?

  30. If one of your friends didn’t like me, how would you react? 

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