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150 Random Questions To Ask A Guy

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

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If you’re looking for topics to talk about with the men in your life, then our collection of random questions to ask a guy are just what you need.

You might think it’s hard to strike up conversations with guys, but it’s really not that difficult. Even things to ask a guy that might seem odd can lead to some interesting chats.

The questions we’ve listed below are from a variety of different topics and backgrounds. We have some deep ones and some weird ones, jumbled into one big random selection!

These are just the questions you need to start light-hearted and deep conversations with any guy you meet!

Best Random Questions To Ask A Guy

1. If you were stranded in the wilderness, would you be able to survive for a month?

2. Who was your childhood crush?

3. Where was the best place you’ve ever been on holiday?

4. What’s the weirdest thing you’ve ever eaten?

5. What would be the ultimate pizza topping?

6. Who’s your favorite sports star?

7. If you were the ruler of your own country what would be the first law you would introduce?

8. What’s the most fun thing someone could have in their backyard?

9. If you had to take me on a spontaneous adventure trip tomorrow morning where would we go?

10. Have you ever been kicked out of a bar? If so, what happened?

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11. Would you rather be the hero in a film or the villain?

12. What’s your funniest memory from the last month or two?

13. What language have you always wanted to learn?

14. Could you eat 10,000 calories in a day? What food would you eat?

15. How many chickens could you take on in a fight and win?

16. How many shots of tequila do you think you could drink in a night out?

17. Are you more into weight lifting or cardio when you exercise?

18. What would be the top 5 bars you would choose for a bar crawl nearby?

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19. If there was a zombie apocalypse, what would be your weapon of choice?

20. Would you date an older woman? If so, how much older?

21. If you could jump on a plane and be anywhere by the morning where would it be?

22. If you won the lottery, what would be the first thing you’d buy?

23. If you could swap places with any person in the public eye, who would it be?

24. What’s the one thing you would like to change about yourself?

25. What’s more important, personality or looks?

26. What’s the fullest you’ve ever been?

27. What would you do if you could turn invisible?

28. What would be the funniest thing to fill a piñata with?

29. What’s your go-to karaoke song?

30. What’s the most useful thing your parents taught you?

31. Who’s your biggest idol?

32. If you were a girl, what would you be called?

33. Could you survive in the wilderness for a month?

34. Who would win in a fight between you and Rocky Balboa?

35. What would happen if you gave up social media for a year?

36. Could you survive if you were stranded at sea for ten days?

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37. What would be the first thing you said to an alien?

38. What’s the worst thing you’ve ever eaten?

39. Would you rather be best mates with Donald Trump or Vladimir Putin?

Random Questions To Ask A Guy To Get To Know Them Better

40. What’s the most embarrassing moment that sticks of your life so far?

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

42. What movie made you cry with laughter?

43. What’s the worst alcoholic drink combination you can think of?

44. What swear word would you make up, and what would it mean?

45. If you woke up as a pigeon, what would you do?

46. If you could come back as any animal after death, what animal would you come back as?

47. What types of behaviour make you think a person is really creepy?

48. What’s the strangest dream you’ve had?

49. What superpower would you least like to have?

50. Does your star sign match your personality? If so, why?

51. What would be your dream career?

52. If you had a magic lamp, what three wishes would you ask for?

53. Where in the world would you hate to visit?

54. What’s your favorite dinosaur?

Random questions to ask a guy favourite dinosaur

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55. Suppose you had the choice of your parents walking in on you having sex or your boss. Who would you rather?

56. If you could break any law without any consequences, which one would it be and why?

57. What’s your favorite sounding word?

58. What’s the worst pain you’ve ever experienced?

59. What’s the drunkest thing you’ve ever done?

60. If you could collect anything, what would it be and why?

61. What’s the strangest thing you’ve ever done?

62. What’s the most embarrassing thing about your body?

63. If you had to dye your hair a different color, what color would you go with?

64. Is there anything you thought you were awesome at but you’re actually awful at?

65. What’s the most amount of money you’ve spent on a night out?

66. What are your go-to driving songs?

67. What was the last thing you fixed by yourself?

68. What would be the most incriminating thing the police would find if they raided your house?

69. What does your ideal day look like?

70. What alcohol could you drink all night without being hungover the following day?

71. If you were a drag artist, what would you specialize in on stage?

72. What is your most awkward breakup?

Random questions to ask a guy awkward breakup

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73. What would your first music album be called?

74. What was your first-ever job?

75. What would be your worst job?

76. What phobia would be the worst to have?

77. In your head, how old do you think you are?

78. What video game could you play repeatedly?

79. What body part do you hate working out?

Random Questions To Ask A Guy To Start A Conversation

80. Who’s the most overrated musician of all time?

81. Which cartoon character did you have a crush on when you were younger?

82. What’s the proudest moment of your life?

83. Would you rather snore or sleepwalk?

84. If you could get drunk with one person, dead or alive, who would you choose and why?

85. Do you think Bigfoot exists?

86. What would be the first thing you did if you came back as a ghost?

87. What bad habit do you have that people get annoyed at?

88. If you could live in a video game, which game would it be and why?

89. What time in history would you love to go back to?

90. What is your dream car?

Random questions to ask a guy dream car

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91. What would your special wrestling move be?

92. Would you ever eat insects?

93. What are your thoughts about visiting North Korea?

94. If teleportation was real, where would you go?

95. What do you think the world is currently missing?

96. Which three friends would you climb Everest with?

97. What cartoon world would you love to live in?

98. What celebrity annoys you the most?

99. What’s the worst purchase you’ve ever made?

100. If you could take any invention as your own, which would it be and why?

101. What’s your best drinking game?

102. What card game are you best at?

103. What chance do we have of reversing global warming?

104. How would you be remembered at your funeral?

105. What in the future do you think will be made illegal?

106. What would you teach in school?

107. What would be the first thing you would do in Area 51?

108. Would you take someone else’s life to save your own?

Random questions to ask a guy life saving

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109. What would you rather have? A first-class ticket to Mars or be in the next Avengers film?

110. What would be your tactics to survive the hunger games?

111. What are your thoughts on lab-grown meat?

112. What do you consider to be the best form of transport?

113. What food could you not live without?

114. What three things would you take onto a desert island?

115. What war would you rather of been involved in? The First World War or the Second World War?

116. Why do men get addicted to video games?

117. What diet trend have you followed?

118. What comic book would you love to read?

119. What secret club would you like to belong to?

120. What horror movie as a kid scared you the most?

Random Questions To Ask A Guy You Like

121. Who would you love to be stuck in an elevator with?

122. What things make you jealous?

123. What do you look for in a woman?

124. What would you say if I told you I was a virgin?

125. Would you rather your partner read your text messages or look at your internet search history?

126. What are your thoughts on camping?

Random questions to ask a guy camping

127. How many sexual partners have you had?

128. Would you have started a relationship with any of your teachers?

129. When have you overreacted to something minor?

130. Do you have any strange fetishes?

131. If you could go anywhere in the world right now, where would you go?

132. What secret talent do you have?

133. What’re the top 5 things on your bucket list?

134. If you had to be described as any animal in bed, what animal would it be and why?

135. What was it like losing your virginity?

136. Would you date an alien?

137. What would you do if you woke up a woman?

138. Would you go on holiday on your own? If so, where would you go?

139. Describe your perfect first date?

140. What female name do you find the sexiest?

141. What chat-up line works the most for you?

142. What odd routine do you have before going to bed?

143. Who’s your celebrity lookalike?

144. What’s the most embarrassing thing that’s happened on a work night out?

145. What would be your first dance song at your wedding?

146. If you had 10 million dollars, what would you buy first?

147. What are your thoughts on having ten wives?

148. What’s something you wouldn’t do no matter how much persuasion you got?

149. What strange things would someone find in your room?

150. What’s a dealbreaker for you when it comes to relationships?

Looking For More Questions?

Dirty Questions to Ask a Guy – A dirtier collection of questions that could lead to sparks flying between you and him.

Questions Girls Are Afraid To Ask Guys – Ask the questions to guys you’ve always wanted to but never got around to doing.

Questions To Ask Your Crush – Got a crush on someone? Here’s a list of useful questions to ask them.

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.