60 Good & Funny questions to ask a guy

Relationships, regardless of who you are, are all about communication – without communication, you won’t really have a strong relationship. Who’s to say the conversations you have can’t be funny?

If a couple decides to spend the entire day together without going out, what are they going to do? There has to be some funny entertainment nesting in there somewhere. Today, we are going to bring you some good & Funny questions to ask a guy.


  1. If your life was turned into a movie, what character would fit you the best?
  2. What’s your favorite childhood memory?
  3. Would you miss a sports game for me?
  4. What’s the worst lie you have ever told?
  5. Did you ever get caught in a lie?
  6. If you were suddenly turned into a woman, what would you do?
  7. As a woman, how would you spend your day?
  8. Would you ever dress up as a girl?
  9. Would you rather be dumb and beautiful or smart and ugly?
  10. If you could describe yourself in 5 words, which 5 words would you use?
  11. Do you have a celebrity crush?
  12. Have you ever had a man crush?
  13. What is your favorite movie?
  14. If you could have any super power in the world, which power would you want to possess and why?
  15. Where was your favorite hiding spot as a child?
  16. What age did you learn to drive?
    Growing up, what is your fondest memory?
  17. Did you ever play doctor as a child and whom did you play with?
  18. What is your favorite animal and why?
  19. If you could be any animal in the world, which one would you choose and why?
  20. If you could be any celebrity in the world, who would you want to be and why?
  21. Has anyone ever caught you naked?
  22. Have you ever taken off your clothes in public?
  23. What is the meanest thing you have ever done to get back at someone?
  24. Do you believe in love at first sight?
  25. What’s your favorite thing to do on the Internet?
  26. If money and your career didn’t matter, where in the world would you choose to live?
  27. What is your biggest regret in life?
  28. If you could change anything about your face, what would you change?
  29. Do you have a book that you simply could not put down?
  30. What television show do you wish you could see more of?
  31. If your life were a sitcom, what would the title be?
  32. Did you ever walk in on anyone naked?
  33. Out of all the pet-peeves you have, which one do you think is the strangest?
  34. Is it better if you beg for forgiveness or ask for permission?
  35. Are you superstitious? If so, what are you superstitious about?
  36. Have you ever kissed a boy?
  37. What are the nicest things anyone has ever said to you?
  38. What is the nicest things you have ever said to anyone?
  39. What are your four major weaknesses?
  40. Are you spiritual or religious in any way?
  41. Which do you think is better – a book or a movie?
  42. What’s your favorite song?
  43. If you could write a song, what would it be about?
  44. If you were a waiter and the customer was rude to you, would you do something bad to their food?
  45. How do you handle a person if you don’t like them?
  46. Where would you prefer to live – the beach, city or country?
  47. Do you think of yourself as being naughty or being nice?
  48. Do you have a favorite food?
  49. What type of food do you absolutely hate?
  50. If you had a choice to pick only one meal to eat for the rest of your life, what would you choose?
  51. If you were abandoned on an island, what would you do?
  52. What is your dream job?
  53. What is your funniest childhood memory?
  54. What is your most embarrassing memory ever?
  55. What is your biggest fear?
  56. If you were able to read minds, whose mind would you like to read?
  57. Based off of my personality and body parts, what nickname would you give me?
  58. In school, did you ever cheat on a test? If so, which subject?
  59. Did you ever have a crush on a teacher?
  60. What’s the funniest person you know?


These questions are meant to be used as a starting point and are not a set-in-stone list that you must ask the guy. You can take this list and use it as a guideline – pick and choose what you want. It may even inspire you to come up with questions on your own.