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100 Weird Questions To Ask A Guy

A photo of Tom who is the Co-Founder of Questions About Everything

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If you want to get a deeper insight into the man in your life, these weird questions to ask a guy will provide you with some interesting things to talk about.

Whether you ask them to a random boy or your boyfriend, you’re sure to end up with some strange, and at times, stupid conversations!

Not all of them are stupid questions to ask a guy, but some of them stray close to the edge. We have some interesting things to ask the guy in your life!

If you’re looking for weird questions to ask your boyfriend or just a random guy, this list has all the bizarre questions you’ll ever need.

Best Weird Questions To Ask A Guy

weird questions to ask a guy desert island

1. What celebrity would you love to be stuck on a desert island with?

2. What strange phobias do you have?

3. What would your last meal on death row be?

4. What do you dislike most about being a man?

5. If you could have a drink with anyone from history, who would it be and why?

6. Where’s the strangest place you’ve been on a date?

7. What’s the strangest thing you’ve been to the hospital for?

8. What’s the longest you’ve been without sex?

9. If you were the opposite sex for the day, what would you do first?

10. Would you rather live in a world without sport or a world without women?

11. What accents can you do?

12. Do you have any strange fetishes?

13. What’s the strangest work experience you’ve ever had?

14. What’s the worst country you’ve traveled to?

15. Were you ever attracted to one of your teachers?

weird questions to ask a guy teacher

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16. If money was no issue, what invention would you like to come up with?

17. What would you do if you woke up tomorrow as a baby but had all your recent memories and experiences?

18. What’s a strange thing that turns you on?

19. What’s the most bizarre fact you know?

20. What type of funeral would you like to have?

21. How often do you drive somewhere and not remember how you got there?

22. What was the most pointless subject in school?

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weird questions to ask a guy pointless school subject

Next: Flirty Would You Rather Questions

23. What’s your favorite part of your body?

24. What was the most pointless rule you had in your house as a child?

25. What medical breakthrough would you like to see in your lifetime?

26. What game do you dominate when you play it?

27. What scene from a movie scarred you for life?

28. Who’s the most overrated band or musician?

29. What’s the most boring activity you do with your partner?

30. What would be your specialty dish if you owned a restaurant?

31. What part of your body would you like to be robotic?

32. Would you go onto an alien spaceship if they invited you on?

33. What would your perfect man cave have in it?

weird questions to ask a guy man cave

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34. Who would win in a fight between James Bond and Chuck Norris?

35. If you could have a miniature version of any wild animal, what would you choose?

36. If you could create a new sea creature, what would it be called/look like?

37. When was the last time you drooled in bed?

38. What’s the ugliest piece of clothing you own?

39. What’s the longest amount of time you have been awake?

40. Would you still eat meat if you had to kill the animals yourself?

41. If you had to choose, which historical war would you have taken part in?

42. What’s one thing you will never buy again?

43. Who’s the most overrated film producer?

44. What’s your worst social media experience?

weird questions to ask a guy social media

Next: Questions to Ask Your Crush

45. What was the last thing you did that made you and others cringe?

46. How often does your brain go on autopilot?

47. What cheap item massively exceeded your expectations?

48. What do you think should be made illegal that isn’t?

49. Do you have any restaurant horror stories?

50. If you could be a fly on the wall of any building, where would you go?

51. Where’s the cheapest place to buy sanitary towels?

52. What would you do to occupy your time in prison?

53. What was the most embarrassing thing you’ve had to do out of politeness?

54. What’s one thing you’ve done to a person that you’d hate them to have done to you?

55. What age would you like to live until?

weird questions to ask a guy age expectancy

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56. What extreme sport would you love to do but are too scared to try?

57. What gives you motivation every time you wake up?

58. Is the area where you grew up famous for anything?

59. What celebrity couple would you like to be your Mom and Dad?

60. What fact do you wish you had never learned?

61. What would people say about you in your funeral speech?

62. What regrets do you have in life?

63. Have you ever made any strange life decisions?

64. Do you think the invention of alcohol was a good thing?

65. What view would you love to have out of your toilet window?

66. Would a movie about your life be a one-hit-wonder, or would there be a sequel?

weird questions to ask a guy movie

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67. Which one of the Avengers do you think you could take in a fight?

68. What’s the most useless piece of knowledge you know?

69. What event in your life makes you ashamed?

70. If you were the newly appointed world leader, what would you change first?

71. Have you ever cheated or been cheated on?

72. Would you rather live in permanent darkness or permanent winter?

73. Do you think ghosts exist?

74. What would you have written on your tombstone?

75. What conspiracy theory do you think is true?

76. Is your life how you imagined it would be as a child?

77. Tell me your favorite joke?

weird questions to ask a guy joke

Next: Random Questions To Ask a Guy

78. Who do you consider to be your hero?

79. How do you think your ex-partner would describe you?

80. What would be the worst thing you could put into a pinata?

81. What would be your way of seeking revenge on someone you dislike?

82. How do you show someone you love them?

83. Do you believe that someone hears you when you pray?

84. What age do you feel now?

85. Do you enjoy being at home or traveling around the world?

86. Do you prefer Coke or Fanta?

87. What’s your first ever picture on Facebook?

88. If you had no money concerns, what business would you startup?

weird questions to ask a guy business

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89. If you were reincarnated as a vegetable, which vegetable would you want to be?

90. What was your first swear word?

91. What movie quotes have you used in real life?

92. Which celebrity do you think you look like the most?

93. Would you like to watch hockey without a referee?

94. At what age do you want to retire?

95. What sport do you wish you were world-class at?

96. What’s the worst car you’ve owned?

97. What are your thoughts on a 4-day working week?

98. If you owned a luxury yacht, what would you call it?

99. Have you ever had a crush on your best friend’s mom?

100. What do you think of women who fart in front of you?

Looking for more questions?

Questions girls are afraid to ask guys – The questions women daren’t ask men. Dare you ask these questions to the guy in your life?

Dirty questions to ask a guy – Want to take things up a notch or two between you and the man in your life? These questions are designed to do just that!

A photo of Tom who is the Co-Founder of Questions About Everything

Tom Stevenson

Co-Founder of Questions About Everything

Tom is a travel writer and Co-Founder of Questions About Everything. He grew up in the UK and enjoys spending his time traveling to new places, supporting Liverpool FC, and blogging about his adventures. He spent two years teaching English in Barcelona and frequently utilized question games and conversation starters as part of his lesson plans. As an EFL teacher, he took full responsibility for planning and delivering lessons, frequently employing creative and diverse questions to engage the children in conversation. Learn more about Tom on our About page.