Funny Questions to Ask a Guy

Funny Questions to Ask a Guy
By Soma Banik Updated

Who does not want to laugh? Laughter is such a thing that almost everyone is hungry for that. But, how difficult or easy is it to think of funny questions to ask a guy? Should I ask only talk about memes or show him some funny YouTube videos? Well! Undoubtedly, you need to have a clear idea about his preferences. And, we can understand that right now your mind has become logged with doubts and queries. Aha! Don’t worry at all. Because as always, we have a solution for you.

100+ Funny Questions to Ask a Guy: Tickle His Funny Bones

It is definitely not an easy task to impress a person with humor. But, we strongly believe that we can help you. Here, we have compiled a list of top 100+ funny questions to ask a guy. Be ready to gift him some hilarious memorable moments.

  1. If a movie is made on your life, then what would be the name of your character?
  2. If suddenly a pie is thrown at you, then which flavor would you love to taste?
  3. In a beautiful morning, if suddenly your crush comes at your doorstep and wants to marry you, how will you react?
  4. What is the best meme you have ever read?
  5. How many scores would you give to my humor quotient?
  6. If you ever find yourself on a lonely island on your birthday, then with whom would you celebrate?
  7. Do you remember any situation, where you laughed so hard that you almost peed in your pants?
  8. Would you kiss your bride if she breathes bad on the day of your marriage?
  9. What is the best punch-line you have ever heard of?
  10. If a beautiful lady requests a date night with you, then how would you respond?
  1. If you find a frog with a crown, then which story would come to your mind first?
  2. What is the funniest compliment you have ever received?
  3. Do you find your lady boss attractive?
  4. What is the funniest nickname you have ever been given?
  5. If somehow you become an intimate part of a woman’s body, then which one would you choose?
  6. Do you love to fantasize beautiful ladies?
  7. What is the best adult joke you have ever read?
  8. If you ever participate in a show like Big Brother, then what would be your strategy?
  9. Are you naughty?
  10. Which is the one thing that makes you crazy about a woman?
  11. If suddenly your yawn becomes viral, then what would be your reaction?
  12. Which is the most bad-ass funny thing you have ever said to a lady?
  13. What is the silliest thing you have done in hangover stage?
  14. If your wife and mom fight over a trivial issue, then which side would you take?
  15. What do you do in a boring office meeting?
  16. What is the funniest thing you have done in front of your crush?
  17. Have you ever had a crush on your school teacher?
  18. Coffee with a celeb or coffee with your date – what would you prefer?
  19. Have you ever farted in a meeting?
  20. Have you got caught while watching an adult movie?
  21. What is the one nickname you have, that everybody laughs at?
  22. A cozy evening with your lady love – what is the first thing would you do to impress her?
  23. Have you ever tried to make a girl crazy by applying a sexy perfume, as the advertisements suggest?
  24. If I call you extremely handsome, then would you take that as a hint of a proposal?
  25. Which funniest movie have you watched till date?
  26. How would you introduce your girl to your mother?
  27. What is the unique thing you do in morning?
  28. Have you ever kissed anyone before?
  29. Do you turn on easily?
  30. Have you ever sneezed at anyone’s face?
  31. Have you ever been in an embarrassing situation?
  32. What is the silliest thing you believed as a child? In fact, it took you a long time to understand that you believed a wrong thing.
  33. Have you ever got a sex toy on your birthday?
  34. Which food makes you happy, but others mostly find that boring?
  35. Which is the one thing you kept on your wishlist for a very long time? But finally, when you could afford, you didn’t buy that.
  36. If you suddenly find that everyone in the office actually has heard your monologue, then how would you react?
  37. Have you ever had experienced ‘Friends with Benefits’ moments?
  38. Which is the funniest villainous character according to you?
  39. Except for ‘Stone, Peper, Scissor’ game, which is the best game to solve disagreements?
  40. Who can make you laugh really hard among your friends?
  41. Which country would you like to visit as a President of a country?
  42. Which movie scene would you like to recreate on your honeymoon?
  43. How do you enjoy holidays?
  44. Do you get bored with preaching?
  45. If you ever get a chance, then would you go back to your previous relationship?
  46. What is the funny thing about me?
  47. Do you have any theme song in your life?
  48. What is the one thing you are best at?
  49. Who comes often in your wildest dreams?
  50. What is the funniest prank you have ever made on someone?
  1. Have you ever met your doppelganger?
  2. Clean shaved or bearded look – which one is your favorite?
  3. If suddenly a bunch of girls becomes crazy for you, then how would you handle them?
  4. If your mom finds you kissing a girl, then what would be your reaction?
  5. Would you ever marry the daughter of a mafia don?
  6. If you find that your girlfriend can fly like Superman, then how surprised would you be?
  7. Have your parents ever caught you doing something really bad-ass?
  8. What is the one thing, everyone finds charming about you?
  9. How romantic are you?
  10. What is the one food you ask everyone to taste, but they never do?
  11. If the ugliest girl in your office who actually has a golden heart, ever proposes you, then would you accept that?
  12. How long did it take you to understand that Santa never gave you any gifts?
  13. Which cartoon character is your all-time favorite?
  14. If given a chance, then how differently would you like to live your life?
  15. What was the first slang you learned?
  16. Do you still blush when you see your favorite actress on TV?
  17. Which movie that you went to watch in a theatre with family, turned out to be the worst movie of all-time?
  18. How do you keep yourself happy?
  19. When did you lose your virginity?
  20. Have you ever met anyone who looks exactly like a Barbie Doll?
  21. In which standard, you finally understood the real meaning of love?
  22. What is your favorite accessory?
  23. Which is the one unusual thing you always carry with you?
  24. One thing that you never leaves your house without?
  25. Have you ever fought with a real bad guy?
  26. What is the one thing you dislike about ‘Cinderella’?
  27. Which animation movie did motivate you?
  28. Your favorite funny quote that has a deep philosophical catch.
  29. Do you believe in casual datings?
  30. If you suddenly find your office boss in the same restaurant where you are currently dating someone, then would you hide or would you just walk in front of him hand-in-hand with her?
  1. What is the craziest thing you have done on a date night?
  2. Has anyone proposed to you in the recent times?
  3. Has anyone ever called you a party pooper?
  4. If in a game, you are asked to kiss a random girl in a shopping mall, then how would you tackle that?
  5. Is there any video that always makes you go ‘rofl’?
  6. Is there any perfume in your collection that can drive any woman crazy?
  7. What is the most insane thing you have ever been gifted?
  8. If you find two of your best buddies dating each other, then what would be your reaction?
  9. Have you ever laughed insanely in front of a bunch of unknown people?
  10. If suddenly you find out that you and your best friend have fallen in love with the same girl, then what would you do?
  11. Have you found your lucky charm yet?

It is not easy to tickle a funny bone of a person. But, we are pretty sure that the above 100+ funny questions to ask a guy would make him go crazy. Some of the questions are close-ended, but you can always make them open-ended so that you two can have a long conversation. And oh yeah! Don’t forget to order some delicious and sensuous foods. So, are you ready to give him an amazing time? Wish you a good charm.


  • Never take a pause in between.
  • Let him explore all the points.
  • If you find him laughing a lot on a point, then add some extra layers to that so that he can have some more fun times.
  • Do not force him to answer in case he feels uncomfortable.