160+ Questions To Ask Your Boyfriend to Make Him Smile [2022]

By January Nelson Updated February 1, 2022

A good relationship requires you to be open and honest with each other — about anything and everything. It doesn’t matter whether you’re on your first date or whether you’re already living together. There’s always more to learn, so here are some great questions to ask your boyfriend:

Dirty Questions

When you’re dating someone, you should feel comfortable talking to them about your sex life. You shouldn’t be embarrassed about bringing up naughty topics when you’ve already seen each other naked. Who knows? Asking a romantic question might even get you in the mood. If you want to get frisky, here are some of the best dirty questions to ask your boyfriend tonight:

1. What is your favorite toy to use in the bedroom?

2. What is the weirdest thing you’ve masturbated to recently?

3. Where is your favorite place to have sex?

4. Does dirty talk turn you on or do you prefer actions over words?

5. What kind of porn gets you off the fastest?

6. What is your biggest fantasy?

7. If you could sleep with any celebrity, who would you choose?

8. What is the dirtiest dream you’ve ever had?

9. Which part of your body do you consider the sexiest?

10. How long do you think foreplay should last?

11. What is your biggest turn-on?

12. What is your biggest turn-off?

13. Has someone ever walked in on you while having sex?

14. Do you prefer rough or gentle sex?

15. Do you prefer being the dominant one or the submissive one?

16. Have you ever gone skinny dipping?

17. Have you ever played strip poker?

18. What do you consider the most attractive part of the female body?

19. Do you sleep naked?

20. What is your favorite sex position?

Personal Questions

If you want a committed relationship with a guy, instead of a temporary fling, then you shouldn’t hesitate to ask personal questions. After all, genuine relationships are created by being completely transparent with each other. You should let your boyfriend see the real you — and since some guys have trouble opening up, you should ask him plenty of questions to get to know him better, too.

1. What was your first kiss like?

2. What is your dream job? Has it changed since you were a child?

3. What is the worst thing you’ve done to another person?

4. When was the last time you cried in front of someone?

5. What is your love language?

6. What is your zodiac sign?

7. What is your MBTI?

8. How did you meet your best friend?

9. What are your biggest pet peeves?

10. What are your biggest guilty pleasures?

11. Where did you grow up?

12. What was the best vacation spot you’ve ever visited?

13. Are you close with your parents?

14. Are you a religious person?

15. What is one thing you couldn’t survive without?

16. What is the most interesting fact about you?

17. How many pets do you have? Did you have any when you were little?

18. What television shows have you been bingewatching lately?

19. What’s your middle name?

20. What is your bad habit?

Intimate Questions

Pillow talk is incredibly important. When you’re in in bed together, you don’t want to sit next to each other in silence. You should ask a cute question instead. Keep in mind, when you’re in a serious relationship, no topic is off the table. You can ask any question that pops into your mind.

1. What is the best piece of advice you have ever received?

2. What book holds the biggest place in your heart?

3. Have you ever stolen something?

4. Have you ever cheated on someone?

5. What do you wish more people knew about you?

6. Do you consider yourself an introvert or an extrovert?

7. Would you rather stay home or go out on a weekend?

8. Why do you consider your best friend your best friend?

9. What is your favorite compliment to receive from the opposite sex?

10. How many times have you been in love?

11. Do you consider yourself successful?

12. Who are you sad about losing touch with over time?

13. Do you believe in soulmates?

14. Would you ever take back a cheater?

15. Who is your role model when it comes to love?

16. What do you miss the most about your childhood?

17. What do you wish you could change about yourself?

18. What life advice would you give the younger version of yourself?

19. What makes you feel loved and appreciated?

20. What inspires you?

Funny Questions

A fun question can lighten the mood during a conversation. It can make you laugh. It can be exactly what you need in order to turn a quiet dinner date into a fun evening that lasts well past midnight. Here are some funny questions to ask your boyfriend in order to get a chuckle out of him:

1. What do you consider couple goals?

2. What is the silliest pickup line you’ve ever used?

3. What was your dumbest injury?

4. What is the weirdest thing you believed while growing up?

5. What was your most awkward date like?

6. What was the funniest movie you’ve ever seen?

7. What’s the weirdest thing in your search history?

8. What is your biggest kitchen fail?

9. What is your least favorite app that you can’t stop using?

10. Do you believe in aliens?

11. Which celebrity do you wish you could swap lives with?

12. Have you ever eaten a bug?

13. If you were a ghost, who would you haunt?

14. What is your least favorite word?

15. What is your most embarrassing moment?

16. Have you ever freaked out while meeting someone famous?

17. Which reality TV show do you think you would win?

18. What is the worst joke you can come up with off the top of your head?

19. What comedians have you seen perform live?

20. What makes you feel old?

Sexy Questions

When you’re in a romantic relationship, you need to keep the spark alive. You can do this by going out on exciting dates and trying new moves in the bedroom. However, you can also keep your boyfriend interested by asking a good question. Don’t forget, words can be as meaningful as actions.

1. Who is your favorite porn star?

2. What type of woman turns you on?

3. Do you consider yourself a good kisser?

4. What do you think you’re best at in the bedroom?

5. What is one thing you would never do in the bedroom again?

6. When do you feel the sexiest?

7. Where do you like being touched the most?

8. What is your favorite type of lingerie?

9. When is your favorite time of day to have sex?

10. Do you prefer the lights on or off?

11. What is the hottest sex scene in any movie?

12. What is your favorite song to listen to during sex?

13. Where do you want to have sex that you’ve never tried before?

14. Where is your favorite place to be kissed?

15. Have you ever been to a strip club?

16. What would your stripper name be?

17. What celebrity do you think would be the best in bed?

18. If you could buy anything from a sex shop, what would it be?

19. What is your favorite thing to see me wearing?

20. Do you consider yourself kinky?

Relationship Questions

In order to get to know your boyfriend better, you might want to ask about a past relationship. After all, his history has shaped him into the man he is today. In a healthy relationship, you can talk about exes without feeling jealous or awkward, so if you have an important question, don’t be afraid to ask.

1. What is the craziest thing you’ve done after a breakup?

2. Who is your favorite ex-girlfriend?

3. At what point do you consider someone your girlfriend?

4. How old were you when you lost your virginity?

5. Have you ever had an STD?

6. Have you ever regretted sleeping with someone?

7. Have you ever had a one-night stand?

8. Where is the weirdest place you’ve ever had sex?

9. What is the dumbest thing you’ve ever done to get laid?

10. Have you ever cried during sex?

11. How many people have you kissed?

12. What is the best sex you’ve ever had?

13. What is the worst sex position you’ve ever tried?

14. Have you ever had sex in public?

15. Have you ever had sex in the shower?

16. What is the most amount of sex you’ve had in one day?

17. What is the most embarrassing thing you’ve ever said during sex?

18. What has been your longest dry spell?

19. What was your most embarrassing boner?

20. Are you a member of the mile high club?

Deep Questions

A great way to build relationships is by having a deep conversation. Although it’s fun to talk about books and movies and video games, every once in a while, you should bring up deeper subjects. Talk about the universe. Talk about your insecurities. Talk about the beauty and darkness of being a human. Regardless of the topic, you should never be afraid to ask your boyfriend a serious question.

1. What is your biggest fear in life?

2. What is the worst thing about being a guy?

3. What is your favorite thing about being a guy?

4. What are you willing to die for?

5. Do you have any superstitions?

6. Are there any family traditions you want to pass down to your own children?

7. What would you do if you had 24 hours to live?

8. What do you want your last meal to be?

9. If you went to prison, what would it be for?

10. If you could bring back someone who died, who would it be?

11. Do you believe in karma?

12. What movie has influenced you the most?

13. Do you consider yourself a good person?

14. When do you think murder is warranted?

15. What is your proudest accomplishment?

16. If you could change one thing about your past, what would it be?

17. What do you think is overrated?

18. What do you think is underrated?

19. Do you have a hunch about how you’re going to die?

20. Do you believe every life has a purpose?

Conversation Starters

Good looks aren’t enough to make a man interested in you. An interesting conversation is going to set you apart from your competition. That’s why you need to approach him with a great question. Make it something unique, something he is going to remember forever.