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271 Questions to Ask Your Boyfriend Before Getting Serious

Use these relationship questions to get to know each other better and deepen your connection.

It's weird to think your boyfriend had a whole life before you, but the truth is he absolutely has. And while there is no doubt the two of you have gotten to know each other well throughout your courtship, there are still things you don't know, and maybe never even thought to ask.

In an effort to help you get to know your beau just a little bit better, we've compiled a list of relationship questions to introduce when the time feels right. After all, you never know what you'll uncover with a few simple prompts. One fun question might lead to a more serious answer regarding your boyfriend's relationship history or something equally as interesting. If anything, they're sure to unearth a few interesting stories and inspire a slew of deep conversations, contestations, and anything in between. Check out our list of questions to ask your boyfriend to get started.

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Fun Questions to Ask Your Boyfriend

Below, you'll find a variety of questions to ask your boyfriend, from conversation starters to more personal prompts. You can use this list to uncover new information or simply pass the time. Always remember, when you run out of things to talk about with your boyfriend, fun questions are a great way to fill the void.

Conversation Starters to Use With Your Boyfriend

couple smiling and talking on a couch
Shutterstock / ArtFamily
  1. Have you ever been to an amusement park?
  2. What's your ideal date?
  3. How long have you known your best friend?
  4. Who was your first celebrity crush?
  5. Are you a germaphobe?
  6. What's the best Halloween costume you've ever seen?
  7. Do you remember your first kiss?
  8. What's your dream car?
  9. Are you a big napper?
  10. Do you like your job?
  11. Do you have any serious allergies?
  12. If you could be anyone else for a day, who would you be?
  13. Did you ever have braces?
  14. How do you take your coffee?
  15. What's your favorite book?
  16. Do you know how to braid hair?
  17. What's your favorite city?
  18. Did you have a nickname growing up?
  19. Are you a good cook?
  20. Do you like getting up early or are you more of a night owl?
  21. Where were your parents born?
  22. What's one guilty pleasure you refuse to give up?
  23. What's your favorite pop culture moment as of late?
  24. What's your favorite food?
  25. Are you good at karaoke?
  26. In your opinion, what's the perfect conversation starter?
  27. Are you superstitious?
  28. Have you ever been hospitalized?
  29. Are you into astrology?
  30. What do you prefer, cats or dogs?
  31. What was your favorite subject in school?
  32. What's the best mistake you've ever made?
  33. What would be a cool hidden talent to surprise someone with?
  34. Are you a good plant dad?
  35. Where are you originally from?
  36. Do you have a favorite dessert?
  37. How many times did your family move growing up?

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Random Questions to Ask Your Boyfriend When Bored

couple sitting on a couch holding hands asking each other random questions
Shutterstock / Goksi
  1. Who's your favorite fictional character?
  2. What's the nerdiest Halloween costume you've ever worn?
  3. Can you tell me about your most embarrassing moment?
  4. What's the weirdest thing you ever did in school?
  5. What's the craziest thing you've ever done on vacation?
  6. What does your own personal hell look like?
  7. If you could go back and live during any era in history, which would you choose and why?
  8. How often do you eat out?
  9. Is there anything you love but most men hate?
  10. Have you ever been skydiving?
  11. Does listening to music with ads bother you?
  12. Do you think you're an animal empath?
  13. Have you ever thought about collecting seashells?
  14. Do you use your top sheet?
  15. Do you have a lot of strong women in your life?
  16. How mad would you be if you had to go back to using a flip phone?
  17. Do you prefer making coffee at home or buying it at a cafe?
  18. What's your favorite milk substitute?
  19. Would you rather explore another planet or the bottom of the ocean?
  20. What's the biggest faux pas you've ever made when traveling?
  21. What's the best way to avoid an awkward silence?
  22. Can you tell me about your first crush?
  23. What's one place you never want to go to again?
  24. Who do you think has it harder: men or women?
  25. What are your grandparents' names?
  26. What would you do if we broke up and you saw me walking around with a new boyfriend?
  27. What's your favorite outfit of mine?
  28. Would you prefer I ask you a weird question or an intimate question?
  29. Do you like watching movies with closed captioning on?
  30. What name do you wish your parents gave you?
  31. Bidets: yay or nay?
  32. What's your mother's maiden name?
  33. How often do you clean your house?
  34. Do you prefer quilts or comforters?
  35. Do you have a favorite baby name picked out yet?
  36. What's your favorite '90s song?

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Questions Concerning Relationship Dealbreakers

couple sitting on dock looking tense discussing relationship deal breakers
Shutterstock / Sjale
  1. Why did your last relationship end?
  2. What's your biggest pet peeve when it comes to personal hygiene?
  3. What would you do if it ever became clear you don't align with your partner's values and beliefs?
  4. What are some annoying habits you can't stand in a housemate?
  5. Do you think you'd survive a long-distance relationship?
  6. What's the worst thing a new partner could do when meeting your family?
  7. What would you do if your partner dramatically changed their hairstyle without giving you a heads-up?
  8. What would you do if I didn't want to participate in any of your favorite activities?
  9. How long could you go without intimacy before addressing it?
  10. Would you ever sacrifice your professional goals so that your partner could achieve theirs?
  11. Would you be able to date someone who rooted for anyone other than your team?
  12. What's one thing you and your partner absolutely have to be on the same page on for a relationship to work?
  13. Would you be OK supporting a partner who didn't want to work?
  14. If you got the sense that you couldn't trust me, would you break things off?
  15. Would you be OK if I started smoking?
  16. Are you OK dating someone who has no interest in domestic hobbies?
  17. Would you forgive me if I cheated on you?
  18. Would you be able to be in an open relationship?
  19. Would you break up with me if I stopped caring about my personal hygiene?
  20. Do you think you'd be able to date someone you work closely with?
  21. What do you think would happen to our relationship if I moved a couple of hours away?
  22. How would you resolve things if you and my best friend couldn't get along?
  23. Would it create problems in the relationship if I were perpetually late to important dates?
  24. How would you react if I suddenly became obsessed with my self-image?
  25. What if your partner developed a kink or a fetish that you really weren't interested in? Would you be able to make the relationship work?
  26. Would you support me if I wanted to undergo extensive plastic surgery?
  27. Would it be a deal breaker if I struck up a friendship with my ex?
  28. Would you break things off if I were always asking for money?
  29. How would you deal with someone who was always rude to your friends?
  30. Would you still date me if I snored loudly every night?
  31. What would you do if you and your spouse had totally different parenting styles?
  32. Would you be able to move on if someone ever got physical with you?
  33. Would you forgive someone if they destroyed your property during a bad argument?
  34. What would you do if you found out your partner was going through your phone?

READ THIS NEXT: 21 Questions For a New Relationship

Personal Questions to Ask Your Boyfriend

gay couple on couch
Shutterstock / RossHelen
  1. What's something your family members don't know about you?
  2. What's something you think you're carrying too much anger about?
  3. How many children do you want in the future?
  4. What's your ultimate dream job?
  5. Do you hold a lot of grudges?
  6. What's something you've been afraid to ask me?
  7. Do you think it's ever OK to lie?
  8. How can you tell the difference between intelligence and cockiness?
  9. Have you ever dumped someone via text?
  10. Do you believe in love at first sight?
  11. Do you prefer reading or watching TV?
  12. Are you a big procrastinator?
  13. What do you like most about yourself?
  14. Do you have a personal hero?
  15. Do you eventually want to buy a house or are you happy renting?
  16. How do you like to be taken care of when you're sick: pampered or left alone?
  17. What's the kindest thing you've ever done for someone?
  18. Do you consider yourself a good friend?
  19. How do you typically respond to stress?
  20. What do you not want to emulate about your parents' relationship?
  21. What's the biggest lie you've ever told a partner?
  22. What's the biggest regret you live with?
  23. Are you close with your extended family?
  24. Have you ever been engaged?
  25. What part of your body are you most insecure about?
  26. How would your family members describe you?
  27. Were you a good student?
  28. When was the last time you cried?
  29. What's the biggest risk you've ever taken?
  30. Do you ever wish you were an only child/Do you ever wish you had brothers and sisters?
  31. Do you struggle with your diet?
  32. Do you worry about making your parents proud?
  33. What's a struggle you've worked really hard to get over?
  34. If money wasn't an issue, would you still want to wake up and go to work every day?
  35. How diligent are you about brushing your teeth?
  36. Do you have any habits you wish you could quit?
  37. Do you sleep soundly through the night?
  38. What's one memory that still brings tears to your eyes?
  39. What's the worst holiday you've ever had?
  40. What's one musical instrument you wish you had learned how to play?

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Questions to Ask Your Boyfriend Over Text

couple on couch using their phones
Shutterstock / Kateryna Onyshchuk
  1. How are you feeling?
  2. Are you awake yet?
  3. What are you having for dinner?
  4. Have you seen the latest episode of (insert favorite TV show here)?
  5. How's work going?
  6. Do you miss me?
  7. Are you listening to anything good right now?
  8. What time are you going to bed?
  9. Do you want me to make you dinner?
  10. Do you want to hang out tonight?
  11. Will you send me a photo of what you're doing right now?
  12. What are you wearing?
  13. Did you remember to water the plants?
  14. How's the weather?
  15. Have you had coffee yet?
  16. What are you watching?
  17. Do you want to FaceTime?
  18. Did you see my new post?
  19. Did anything exciting happen today?
  20. What time did you get up today?
  21. Did you dream about anything interesting last night?
  22. Has (insert pet's name here) done anything cute today?

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Cute Questions to Ask Your Boyfriend

woman at a cafe drinking coffee and asking her boyfriend cute questions
Shutterstock / Prostock-studio
  1. What's your favorite thing about me?
  2. Do you think we'd do better with a dog or a cat?
  3. Do you think we should go to the beach or the mountains for our next vacation?
  4. What's something exciting we should do this summer?
  5. Can I have a kiss?
  6. What's your favorite love song?
  7. What's the funniest thing I've ever done?
  8. Using only one word, how would you describe me?
  9. What holiday are you most looking forward to spending together?
  10. If I were a flavor, what do you think I'd taste like?
  11. If we were to move in together, who do you think should do most of the decorating?
  12. Do you like my hair straight or curly?
  13. If we could go anywhere in the world, where would you bring me?
  14. What's something I could do that would leave you absolutely speechless?
  15. Can I give you a manicure?
  16. …What about a massage?
  17. How has your life changed since you met me?
  18. Where do you want to go for our next date?
  19. Will you hold my hand?
  20. What about me made you want to pursue a relationship?
  21. Do you want to be the big spoon or the little spoon?
  22. Do you remember the day we met?
  23. What do you think made me fall in love with you?
  24. What's something about me that you miss when we aren't together?
  25. Do you think we look good together?
  26. Have you ever had a dream about me?
  27. What do you like better, hugs or kisses?
  28. Do you like when I wear your clothes?
  29. When you think back on when we first met, did you ever think we'd end up here?
  30. What's the next TV series you want to binge together?
  31. Do you sleep better with me in your bed?

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Serious Questions to Ask Your Boyfriend

couple leaning on fence and asking intimate questions
Shutterstock / chuanpis
  1. Do you think it's important for your partner to also be your best friend?
  2. What's the most valuable lesson you've learned from past relationships?
  3. Do you prefer spending time with a partner at home or out doing activities?
  4. Have you lost anyone you love?
  5. Do you believe in evolution?
  6. How long do you think people should date before introducing the families?
  7. Do you ever think about going back to school?
  8. What's the ultimate pleasure you derive from being in a relationship? Not being lonely? Enjoying physical touch? Something else entirely?
  9. Do you believe in euthanasia?
  10. Do you think ignorance really is bliss?
  11. What's something that recently rocked your perception of reality?
  12. Have you accrued any credit card debt?
  13. How would you react if you found out I've previously dated someone of the same sex?
  14. How would you handle a conflict with a neighbor or landlord?
  15. What are you most afraid of happening to us?
  16. Did you vote in the last presidential election?
  17. Have you ever donated to charity?
  18. Would you rather have kids naturally or adopt?
  19. Do you recycle?
  20. Have I ever made you feel belittled or put down in front of other people?
  21. What's more important, physical chemistry or emotional connection?
  22. Do you think gender norms have a purpose?
  23. Are you a believer in capitalism?
  24. What makes you feel old?
  25. Have you ever been in therapy?
  26. Are you able to forge relationships with people who hold opposing political beliefs?
  27. In your opinion, what's the saddest story from history?
  28. What's the worst quality a person can possess?
  29. Does death scare you?
  30. Do you think it's important to leave a legacy after you die?
  31. What would a family member have to do for you to cut them off?
  32. Do you want to start a family?
  33. Do you have a retirement plan?
  34. Have you ever been in love before?
  35. How can I support your interests?
  36. If you won the lottery, what would you do with the money?
  37. What's something that can make you happen, even on your worst day?
  38. What's the best way to get on a deeper level with someone you're seeing?
  39. Besides technological advancements, what's your favorite thing about the modern era?

Juicy Questions to Ask Your Boyfriend

couple kissing in the sunlight
Shutterstock / dekazigzag
  1. How many sexual partners have you had?
  2. How would you like to see our sex life evolve in the future?
  3. Do you like performing oral sex?
  4. What kinds of relationship red flags might present in the bedroom?
  5. What's the best advice you've been given when it comes to satisfying your partner?
  6. What is your ultimate bedroom fantasy?
  7. How do you think we should spice things up the next time we get it on?
  8. Have you ever revealed something during pillow talk you wish you hadn't?
  9. Have you ever thought about filming one of our intimate moments so you can rewatch it over and over again?
  10. Based on previous relationships, what's one thing you know you don't like in the bedroom?
  11. How would you keep the spark alive in a long-term relationship? Frequent visits? Phone sex? Naughty videos?
  12. What's your favorite sex position?
  13. Do you like lingerie?
  14. Can you tell me something you think would turn me on?
  15. How long should sex last, ideally?
  16. Can you guess what kind of underwear I'm wearing right now?
  17. In your opinion, what's the difference between having sex and making love?
  18. Do you like when someone pulls your hair?
  19. What's the weirdest place you've ever gotten it on?
  20. Have you ever had a one-night stand?
  21. What's your favorite sex scene from a movie?
  22. Are you more frisky in the morning or at night?
  23. Have you ever had a friend with benefits?
  24. What are your thoughts on dirty talk?
  25. Are you a big sexter?
  26. Would you ever have a threesome?
  27. How do you feel about using toys in the bedroom?
  28. Do you like listening to music during sex?
  29. Do you like to do it with the lights on or off?
  30. Would you ever want to experiment with BDSM?
  31. Is it important that your partner reaches climax?
  32. Ideally, how many times per week would we have sex?

Wrapping Up

That's it for our list of questions to ask your boyfriend! Be sure to check back in with us soon for similar kinds of content. We've got lots more funny, interesting, and intimate questions to ask the people close to you. You can also sign up for our newsletter to make sure you don't miss out!

Carrie Weisman
Carrie Weisman oversees all SEO efforts at Best Life. She specializes in content optimization and editorial marketing. Read more