108 Random Questions to Ask a Guy

We’ve curated an eclectic list of random questions to ask a guy that guarantees a mix of normal, quirky, and outright unexpected.

Whether you’re seeking to dive into intriguing discussions or simply add a dash of unpredictability to your conversations, we’ve got you covered.

Get ready for a rollercoaster of topics – from the usual to the wonderfully weird!

And if you’re hungry for even more, we’ve got random questions to ask a girl or you can explore our random question generator for an endless supply of conversation sparkers.

But wait, there’s more! As you scroll down, you’ll find links to additional sets of questions that promise to keep the conversation flowing and the laughter rolling.

Ready to embark on a journey of endless curiosity? Let’s dive in!

List of Random Questions to Ask a Guy

1. If you could have any animal as a pet, mythical or real, what would it be?
2. What’s the most unusual talent you possess?
3. If you could live in any fictional universe, which one would you choose?
4. What historical figure would you want to have dinner with?
5. Which movie deserves a sequel that never got one?
6. If you were a superhero, what would be your superpower and costume?
7. What’s the weirdest food combination you enjoy?
   
8. If you had a time machine, would you go to the past or the future?
9. What’s the most beautiful place you’ve ever been to?
10. If you could be any character in a video game, who would it be?
11. What’s the most useless talent you have?
12. If you could eliminate one thing from your daily routine, what would it be?
13. What invention do you think will be obsolete in 10 years?
14. If you were a professional wrestler, what would your entrance music be?
15. What’s the oddest job you can imagine having?
16. If you could have any view from your bedroom window, what would it be?
17. What’s the most recent show you binge-watched?
    
18. If you could time travel only once, where and when would you go?
19. What’s the most bizarre thing you’ve ever eaten?
20. If you could communicate with one species of animal, which would it be?
21. What’s the weirdest dream you’ve ever had?
22. If you were a character in a horror movie, what would be your fate?
23. What’s the most interesting fact you know about space?
24. If you were a wizard, what spell would you use most often?
25. What’s your go-to dance move when no one is watching?
26. If you could have any fictional character as a sidekick, who would it be?
27. What’s the strangest talent you wish you had?
    
28. If you could have dinner with any celebrity, dead or alive, who would it be?
29. What’s the weirdest museum you’ve ever visited?
30. If you could have any job for a day, what would it be?
31. What’s the most unusual place you’ve ever slept?
32. If your life was a genre, what would it be?
33. What’s the most ridiculous way you’ve injured yourself?
34. If you could have any vehicle, real or fictional, what would it be?
35. What’s the weirdest tradition your family has?
36. If you could have a conversation with any fictional character, who would it be?
37. What’s the most unique item you own?
38. If you could have any skill instantly, what would it be?
    
39. What’s the strangest talent someone has discovered about you?
40. If you could choose any accent for a day, which one would it be?
41. What’s the most bizarre piece of trivia you know?
42. If you could have any piece of technology from the future, what would it be?
43. What’s the most interesting piece of art you’ve ever seen?
44. If you could have any three people, living or dead, at your dinner party, who would they be?
45. What’s the most peculiar souvenir you’ve brought back from a trip?
46. If you could have any fictional creature as a pet, what would it be?
    
47. What’s the most outlandish goal you’ve set for yourself?
48. If you could switch lives with any fictional character for a day, who would it be?
49. What’s the weirdest job you can think of that someone must do?
50. If you had to survive a zombie apocalypse, what three items would you grab?
51. What’s the most unexpected compliment you’ve ever received?
52. If you could have any famous painting in your living room, which one would it be?
53. What’s the most unusual nickname you’ve ever been given?
54. If you could be an expert in any field instantly, which field would you choose?
55. What’s the weirdest tradition from another culture that you find fascinating?
    
56. If you could have a conversation with any historical figure, who would it be?
57. What’s the most bizarre food you’ve tried while traveling?
58. If you could have any fictional technology, what would it do?
59. What’s the strangest skill you’ve acquired by accident?
60. If you could have any animal’s ability, what would it be?
61. What’s the most unique holiday celebration you’ve experienced?
62. If you could have any fictional vehicle, what would it be?
63. What’s the oddest thing you’ve ever found while exploring nature?
64. If you could have any mythical creature as a protector, what would it be?
65. What’s the most peculiar habit you’ve developed?
    
66. If you could have any historical artifact, which one would it be?
67. What’s the weirdest thing you believed as a child?
68. If you could have any superpower but only for a day, what would it be?
69. What’s the most surprising thing you’ve learned recently?
70. If you could have any exotic pet, legal and safe, what would it be?
71. What’s the most unconventional talent someone you know has?
72. If you could have any piece of clothing from a movie, which one would it be?
73. What’s the most unexpected place you’ve discovered great food?
74. If you could have any movie prop in your home, what would it be?
75. What’s the weirdest fashion trend you’ve ever tried?
76. If you could have any fictional currency, what would it be and what could you buy with it?
77. What’s the most bizarre story you’ve heard from a family member?
    
78. If you could have any animal as your sidekick, which one would it be?
79. What’s the most unusual skill you’ve learned just to impress someone?
80. If you could have any job for a week, what would it be?
81. What’s the strangest food combination that surprisingly tastes good?
82. If you could have any ability from a video game, what would it be?
83. What’s the most peculiar thing you’ve witnessed in a public place?
84. If you could have any fictional weapon, what would it do?
85. What’s the weirdest hobby you’ve ever had?
    
86. If you could have any celebrity narrate your life, who would it be?
87. What’s the most surprising thing you’ve found at a thrift store?
88. If you could have any magical object from a fantasy world, what would it be?
89. What’s the most bizarre conversation you’ve overheard in passing?
90. If you could have any gadget from a sci-fi movie, what would it do?
91. What’s the weirdest piece of advice you’ve ever received?
92. If you could have any mythical weapon, what would it be and why?
93. What’s the most unusual sport you’ve ever tried?
94. If you could have any animal ability, what would it be and how would you use it?
95. What’s the weirdest thing you’ve seen someone do in public?
96. If you could have any historical document, which one would it be?
97. What’s the most peculiar way you’ve celebrated a holiday?
    
98. If you could have any fictional drug from a book or movie, what would it do?
99. What’s the oddest thing you’ve collected over the years?
100. If you could have any futuristic gadget, what would it be and how would you use it?
101. If you could have any fictional vehicle for your daily commute, what would it be and why?
102. What’s the most unusual thing you’ve witnessed while people-watching?
103. If you could have any historical figure as your mentor, who would it be and what would you learn from them?
104. What’s the weirdest habit you had as a child that you’ve carried into adulthood?
105. If you could have any animal’s ability to communicate with other species, which one would it be and why?
106. What’s the most bizarre piece of trivia you’ve discovered recently?
     
107. If you could have any superpower related to time, what would it be and how would you use it?
108. What’s the most unexpected thing you’ve found in the depths of the internet during a late-night browsing session?

More Questions to Ask a Guy