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100 Romantic Questions To Ask Your Boyfriend To Make Him Laugh

100 Romantic Questions To Ask Your Boyfriend To Make Him Laugh

If you can make a woman laugh, you can make her do anything. But does it work the same for guys? Of course, it does.

If you have a good sense of humor, you’re already halfway to a man’s heart

Imagine that power combined with romance! Nobody can stop you.

Well, that’s exactly what I’m bringing you and more with this article. If you read on, you’ll also have a chance to find out something new about this guy.

That’s right, here’s the ultimate list of romantic questions to ask your boyfriend to make him laugh.

Fun Romantic Questions To Ask Your Boyfriend To Make Him Laugh

couple having a fun conversation

Use these flirty questions as conversation starters and a way to put a smile on his face. Trust me: these are the best fun romantic questions to ask your boyfriend to make him laugh.

1. What is your favorite guilty pleasure movie or TV show?

2. Do you have an alter ego?

3. What’s the most embarrassing thing you would do for me?

4. What was your funniest first date?

5. What part of your body do you like the most?

6. What’s the funniest thing you did when you were drunk?

7. What is the weirdest thing about you?

8. Have you ever gone skinny dipping?

9. If you could have one superpower, what would it be?

10. What is your favorite movie – the one you’d like me to watch?

11. Where’s the craziest place you’ve made out with someone?

12. What was the last thing you searched on your phone?

13. What was the first thing you noticed about me?

14. If you could change one thing about my appearance, what would it be?

15. Who is your celebrity crush?

16. If you had to sleep with one cartoon character, who would it be?

17. Would you rather be with your boss or your favorite college teacher?

18. What’s the worst thing that could happen on a first date?

19. What is your biggest pet peeve about dating?

20. What could give you an ick for someone?

man and woman having fun on a date

21. What is the funniest compliment you’ve ever received?

22. What’s the worst gift you’ve ever received from a partner?

23. What’s the most absurd thing about modern dating?

24. What question do you always ask a woman on the first date?

25. What’s the worst trouble you’ve gotten yourself into as a kid?

26. What is the one thing you would never do at your wedding reception?

27. What is the first thing you notice about a woman?

28. What’s something that I think makes me look cool but actually makes me look ridiculous?

29. If your life was the “expectation vs. reality” meme, what would the two pictures be?

30. If the Internet community decided to cancel you, what would it be about?

31. What’s your favorite snack besides me?

32. If you came with a warning label, what would it say?

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

34. What job doesn’t exist but should?

35. What’s one thing I wouldn’t believe about your personality or life?

36. What is something that everyone looks stupid doing?

37. You’re in a duel. What song is your soundtrack?

38. How many pillows do you sleep with?

39. What romantic song would you sing to me to melt my heart?

40. What’s your favorite babyish nickname?

Deep Questions To Ask Your Boyfriend

couple laughing while on a date

Here’s a list of some more intimate questions to start a deep conversation with your boyfriend or the guy you like. Don’t worry, there are also some fun questions here.

1. What is your biggest regret?

2. What is your worst childhood trauma?

3. Who is your favorite person in your family?

4. What is your biggest stress trigger?

5. What is your wildest dream?

6. If you could have dinner with one person, dead or alive, who would it be?

7. What is your dream job?

8. What was your favorite highschool subject?

9. How do you feel about feminism?

10. Are you pro-choice or pro-life?

11. How do you feel about sex and gender?

12. How important is religion or spirituality to you?

13. What is something that’s always worth the wait?

14. What are some of your non-negotiable moral values?

15. Do you believe in karma, or do you take things into your hands?

16. What’s the worst thing you’ve ever done?

17. What is the one white lie you keep on telling?

18. What is the one thing you’re the most passionate about?

19. What are the top five things on your bucket list right now?

20. Who is your role model?

man and woman on a coffee date

21. What part of your life are you the proudest of?

22. What are you the most afraid of?

23. What kind of personality traits should your best friend have?

24. If you could re-live one moment in your life, what would it be?

25. What’s your favorite memory from childhood?

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

27. Where do you see yourself 10 years from now?

28. What motivates you the most?

29. If you had to choose between love and money, what would you choose?

30. What do you consider to be your biggest accomplishment so far?

Random Questions To Ask

couple having a conversation

Sometimes, you don’t know what to talk about with the man you’re into. But you don’t want to talk about the weather. Here are some random questions to ask him:

1. What is your worst spent money?

2. If you had to eat only one food for the rest of your life, what would it be?

3. What are the three things you would take with you to a desert island?

4. Do you believe in ghosts? Are you scared of them?

5. If you could live someone else’s life for a day, whose life would you choose?

6. Would you rather go back into the past or forward into the future?

7. What’s your favorite zodiac sign?

8. What is the one song you know by heart?

9. What was the last thing you dreamt about?

10. What’s your least favorite color?

11. What do you have to do before going to bed?

12. What movie is overrated?

13. If you put out a magazine, what would you name it, and what would be in it?

14. If the police raided your house right now, what is the most incriminating thing they would find?

15. If your life were a movie, what would it be called?

16. What song would you pay money to never hear again?

17. If you represented Earth while meeting aliens for the first time, what would you say?

18. What was your first cell phone?

19. What was your first car?

20. If you could live anywhere in the world, where would you go?

21. When was the last time you traveled? Where did you go?

22. What’s the worst movie you have ever watched?

23. Have you ever met a celebrity? How was it?

24. What’s the best restaurant in your town?

25. What is the meal you cook the best?

26. What is your favorite personal skill?

27. If you could pick any celebrity to officiate your future wedding, who would it be?

28. What is your favorite emoji?

29. What song do you usually sing in the shower?

30. What’s the most delicious thing in your fridge right now?

Serious Questions To Ask Your Boyfriend

couple looking at each other

These great questions might sound too serious, but they will definitely take your relationship to the next level.

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

2. Where is our relationship going?

3. Do you see a future with me?

4. Do you want to get married one day?

5. Do you want to have children one day?

6. What kind of father do you think you’ll be?

7. What are the girlfriend qualities you’re looking for?

8. Why are you boyfriend material?

9. How would you label our relationship?

10. What is the one thing you could never forgive me for?

11. What relationship standards don’t I fulfill for you?

12. What can I do to make you happier?

13. Would you rather be single or in a crappy relationship?

14. Do you have any regrets regarding our relationship?

15. What would you like to change about romance?

16. How can I support you in achieving your goals?

17. What do you think I miss in our relationship?

18. If you could take one pain away from me, what would it be?

19. What is the one thing you would never apologize for?

20. What annoys you the most about me?

Romantic Relationship Questions To Ask Your Boyfriend

couple lying on couch with dog

Here’s something new on the list of romantic questions to ask your boyfriend to make him laugh. If you want to know more about his love history, these revealing relationship questions are the thing for you:

1. What was your first time like?

2. What do you prefer: to cuddle or kiss?

3. What is your favorite pickup line?

4. What is your favorite song to listen to while making out?

5. What is the most embarrassing text message you sent to a crush?

6. When was the last time you fell in love?

7. What was your most painful breakup like?

8. What is your ideal date night?

9. What was your most embarrassing moment in a relationship?

10. What do you think a healthy relationship is?

11. What are your dealbreakers when starting a new relationship?

12. What was the craziest thing you did for someone you loved?

13. What is your favorite food on a date night?

14. What is your least favorite thing about me?

15. Do you believe in the concept of soulmates?

16. What is my sexiest outfit?

17. When is the right time to say “I love you”?

18. What was your worst romantic fail?

19. What was your longest relationship?

20. Which ex-girlfriend/ex-boyfriend did you love the most?

21. What do you think is the easiest and the best way to break up with someone?

22. Have you ever ghosted someone?

23. Is infidelity ever acceptable?

24. What is your love language?

25. What do you think my love language is?

26. What personality type do you think you are?

27. Why do so many people get divorced?

28. What is the thing that would make you marry a woman?

29. What is the one thing in your romantic history that you’re not proud of doing?

30. What’s the best first kiss you had?

Kinky Questions And Dirty Jokes For Your Boyfriend

couple talking in bed

Spice things up with these hilarious dirty jokes. Even these can be seen as romantic questions to ask your boyfriend to make him laugh – if that’s his sense of humor.

1. What is your biggest turn-on?

2. What can turn you off in bed instantly?

3. Is your name highway? Because I want to ride you all night long.

4. I’m always on top of important things. Would you like to be on the list?

5. Who’s your favorite porn star?

6. Are you a balloon? Because I want to blow you.

7. What’s your favorite bedroom position?

8. Are you from China? Cause I’m China get in those pants.

9. What is your sexiest scene from a movie?

10. Do you have a switch? Because I want to turn you on.

11. What’s your favorite fetish?

12. Are you a campfire? Because you’re hot, and I want some more.

13. What’s one thing you want me to do to you that I haven’t done?

14. Are you an elevator? Because I wanna go up and down on you.

15. What’s the difference between a tire and 365-used condoms? One’s a Goodyear. The other’s a great year.

16. Why does Santa Claus have such a big sack? He only comes once a year.

17. Who’s the most popular guy at the nudist colony? The one who can carry a cup of coffee in each hand and a dozen doughnuts.

18. How is sex like a game of bridge? If you have a great hand, you don’t need a partner.

19. What’s the difference between kinky and perverted? Kinky is when you tickle your girlfriend with a feather – perverted is when you use the whole bird.

20. Why does a mermaid wear seashells? Because she outgrew her B-shells!

21. What do you call a cheap circumcision? A rip-off!

22. What is your biggest dislike in the bedroom?

23. What’s a position you’ve never tried but are curious about?

24. What would you do to me if we were alone right now?

25. What do you think about when you pleasure yourself?

26. How many people have you slept with?

27. Where do you like to be kissed the most?

28. Have you ever slept with one person while fantasizing about someone else? Who was the other person?

29. What is the weirdest thing you used in foreplay?

30. Do you like it slow or rough?

Romantic Riddles With Answers

couple talking in nature

These riddles are funny and incredibly romantic at the same time. So, it must mean that they fit the pattern.

1. What is mine, but only you can have?

Answer: My heart.

2. What did the painter say to her boyfriend?

Answer: I love you with all my art!

3. What did the man with the broken leg say to his nurse?

Answer: I have a crutch on you.

4. What did the boy rabbit say to the girl rabbit on Valentine’s Day?

Answer: Some bunny loves you.

5. What did the boy owl say to the girl owl on Valentine’s Day?

Answer: Owl be yours!

6. What are the three rings of marriage?

Answer: The engagement ring, the wedding ring, and the suffering.

7. What is invisible and makes people suffer from symptoms like sweating and nausea, yet people can’t survive without it?

Answer: Love.

8. He has married many but has never been married. Who is he?

Answer: A priest.

9. It grows and blossoms. It dies and wilts. It happens in the beginning and happens in the end. It can make you cry, it can make you sad, it can make you smile, and it can make you brave. What is it?

Answer: Love.

10. What did the hamburger buy his sweetheart?

Answer: An onion ring!

11. You see him flying around, carrying bows and arrows. Once he hits you with it, all you feel is love, not sorrow. He must have hit us both. Who is he?

Answer: Cupid.

12. I am a nine-lettered word that rhymes with perfection; I am yet another name for love. What am I?

Answer: Affection

13. What fills a room but takes up no space?

Answer: Love in the air

14. I am endless love, and once you enter my world, you are bound for life. What am I?

Answer: Marriage

15. What is that thing that connects two but touches one?

Answer: A proposal ring

16. What did a small nail tell the magnet?

Answer: You are attractive

17. Why should you avoid falling in love with a pastry chef?

Answer: They’ll only dessert you

18. When do you know a turkey is ready to go on a date?

Answer: When it is “dressed”

19. What did the man say about his Korean girlfriend?

Answer: She was his Seoul mate

20. What did number two say to one?

Answer: Are you single?

To Wrap Up:

This list of romantic questions to ask your boyfriend to make him laugh has it all: fun questions, personal questions, cute questions, funny questions, you name it.

But all of these interesting questions have one thing in common: they will help you win your man’s heart and find out a lot about him. Good luck!

100 Romantic Questions To Ask Your Boyfriend To Make Him Laugh Pinterest