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200 Random Questions To Ask Anyone For Unpredictable Conversations

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

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Random questions to ask are fun because they often lead to some weird and wacky conversations whether it’s with friends or people you’ve just met.

The genius of random conversation starters is that they can throw people off guard and lead them to give answers that are a bit more truthful.

Our random questions to ask friends and anyone else cover a range of topics. They can be asked to acquaintances new and old.

If you want to have fun and quirky conversations, this is the list of questions for you.

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Random Questions To Ask Anyone

1. If you were gifted three wishes, what would you wish for and why?

random questions to ask anyone gifted three wishes

2. If you could bring one famous person back from the dead, who would it be and why?

3. Would you rather be a gold medallist in the Olympics or score the winner in a soccer world cup final?

4. If you had a choice of living on Earth or living on Mars, which would you choose and why?

5. If you could travel back in time, what year would you go back to and why?

6. Do you think humans will evolve to look different in the future? What changes will there be to our bodies?

7. What food would be the worst to be allergic to?

8. What’s the most beautiful country you’ve travelled to?

9. If you could have any talent in the world, what would you choose to have?

10. If the world was on the brink of a zombie apocalypse, what weapons would you choose to defend yourself?

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11. What’s the most embarrassing situation you’ve been in?

12. How would you prove you were from the past if you were transported with no clothing or identification in the future?

13. Have you ever broken the law? If so, what did you do and were you caught?

14. If you could swap lives with one of your friends, who would it be and why?

15. What movie could you watch every day for the rest of your life without getting bored?

16. If you could remove one invention from the world, what would it be and why?

17. Have you ever accidentally been caught naked?

18. What’s the worst thing that could be made illegal?

19. If you had the chance to interview one leader of the world, who would it be and why?

20. If you had the money and power, how would you tackle climate change?

21. If you were going to rob a bank, which of your friends would you take with you?

22. What fictional character do you wish were real?

23. What world event would you go back to and change the outcome?

24. What infection/disease would you most like to come up with a cure for?

25. What animal would you be most scared to meet in the wild?

You might also like: Interesting conversation topics

26. What do you think is the meaning of life?

27. When we die, what do you think happens?

28. If you had to pick one animal to back you up in a fight, which animal would you choose and why?

29. Would you rather have the ability to breathe underwater or to be invisible?

30. What are the five most beautiful things in the world?

31. Do you think heaven and hell exist?

32. What accomplishment do you cherish over all the rest?

33. What is always guaranteed to get you in a bad mood?

34. What activity always makes you bored?

35. Would you give mouth-to-mouth to a homeless person if they were dying?

36. What is the spiciest food you’ve ever eaten?

37. What was the last magazine you subscribed to?

38. What would be the worst torture you could receive?

39. What size of bed do you have?

40. What do you admire in life?

41. What was the last mistake you made?

42. What type of cheese is the best?

43. If you were a leader of a cult, what initiation would you introduce?

44. In a word, sum up COVID-19?

45. What do you think about cruise holidays?

46. Knowing what you know now, do you the internet was a good invention?

47. What name would you hate to have been called by your parents?

48. How would the world be different if both females/males were clones of yourself?

49. If you created a public holiday, what would you call it, and when would it be?

50. Have you ever been on a luxurious holiday?

You Might Enjoy The Table Topics Conversation Starters Game on Amazon!

random questions to ask anyone luxury holiday

You might also like: Questions to ask old people

51. What is perfectly legal but creepy?

52. What’s something invisible to the naked eye that you wish people could see?

53. What movie were you most disappointed with?

54. What was your favourite cartoon growing up?

55. Who is your favourite basketball player?

56. What food would taste awful mixed together?

57. If you were able to stop time, what would you do first?

58. What supercar would you own if money was no object?

59. Why do we drink another animal’s breast milk?

60. If conscription into the military was brought back, which out of the Navy, Army or Air Force would you join, and what would your job be?

61. Do you think if the purge were real, it would make the world a better, safer place?

62. If you could turn into an inanimate object, what would it be and why?

63. What has been your favourite Netflix series?

64. What’s the best insult you’ve ever used?

65. If you were a professional boxer, what song would you choose for your ring walk?

66. What was your favourite video game growing up?

67. Who are the greatest musicians ever to live?

68. If you could pick your nickname, what would it be?

69. What are the three most great movies of all time?

70. Who would you like to trade lives with for the day?

71. Which historical figure would you like to have been?

72. What’s a great book you recently read?

73. What was your favourite childhood book?

74. What has been your favourite family vacation?

75. What milkshake flavour do you like the most?

Next: Questions that make you think

76. Do you see yourself as a leader or a follower?

77. Do you ever talk to pieces of furniture in the house? If so, what do you say?

78. What is your favourite time of day?

79. What one word would you use to describe all of your friends?

80. Would you rather win an Oscar or an Olympic Gold medal?

81. What strange noise do you love that most people don’t?

82. What’s the strangest thing in your freezer?

83. What pet peeve do you have?

84. What’s your favourite topping on a burger?

85. Would you complete a man versus food challenge?

86. If you were to collect anything, what would it be and why?

87. What do you like to do on a rainy day?

88. What food looks delicious but tastes terrible?

89. Do you sleepwalk or talk?

90. What has been the best live concert you’ve been to?

91. How do you feel when someone interrupts you while you’re trying to concentrate?

92. Have you ever lied about your age?

93. Have you ever googled your name?

Random Questions To Ask A Guy

If you’re looking for some questions to ask the guy in your life, the following are what you’re after. These random questions to ask a guy will throw up some interesting answers.

94. What would you do first if you found out that you won the lottery?

95. How do you want people to remember you after you are no longer here?

96. If you could go to a bar with three famous people past/present, who would they be and why?

97. Why do men have hair on their bodies?

98. Instead of war, what alternative ways could countries settle their feuds?

99. What film did you last cry at?

100. What dreams and ambitions do you have for your future?

random questions to ask anyone dreams and ambitions

You might also like: Personal questions to ask a guy

101. What’s the funniest thing you’ve seen happen in sports?

102. Do you have a celebrity crush? If so, who is it?

103. When in your life have you felt most in control?

104. If you could speak to the world for 15 minutes, what would you have to say?

105. What phobias do you have?

106. If you could be fluent in any other language, which one would it be?

107. What is the funniest film you’ve seen?

108. If you had to pick your best hairstyle through the years, which one would you choose and why?

109. If you could name your album, what would you call it and why?

110. If you could teleport anywhere right now, where would you go?

111. Would you prefer the world to have zero gravity or friendly alien inhabitants?

112. What’s your guilty pleasure?

113. What’s your earliest memory?

114. What’s your favourite fast-food restaurant?

115. What has been the worst first date you’ve been on?

116. What’s the strangest smell you’ve ever come across?

Random Questions To Ask A Girl

117. What is the weirdest thing you’ve ever fallen in love with?

118. What would you choose as your first dance song?

119. If you could pick any superpower, which would you choose and why?

120. How would you commit the perfect crime?

121. What’s the longest you’ve kept a secret for?

122. What character in the film bridesmaids are you most like?

123. Are you someone that leaves reviews? What has been the funniest review you’ve left?

124. What is more important to you, adventure or stability?

125. What item in your home could you never live without?

random questions to ask anyone home item you couldn't live without

Next: Deep questions to ask a girl

126. If you could have any animal as a pet, what would you choose?

127. Would you rather have a fantastic singing voice or be an award-winning actress?

128. Who’s your favourite actor/actress?

129. What’s your worst habit?

130. Would you rather be YouTube famous or Instagram famous?

131. What does success look like to you?

132. Which person in your life taught you the most?

133. If you were offered the role of president of the United States, would you take it?

134. Did you ever get in trouble in school? If so, what was it for?

135. What animal would you want to be reincarnated as?

136. What advice would you give to your younger self?

137. If you were a ghost, who would you haunt?

138. What’s your most embarrassing drunken moment?

139. What is the best ice cream topping?

140. What is the most interesting fact you know?

141. Would you rather be a famous director or a famous film music composer?

142. Would you rather be feared by everyone or loved by everyone?

143. Would you rather be trapped in a museum or zoo overnight?

144. Do you prefer waterparks or theme parks?

Deep Random Questions

145. If you had three days to live, what would you do in the days you had left?

146. What was the last risk you took in life?

147. What’s top on your bucket list?

148. What is your most treasured memory?

149. Has your life gone the way you thought it would?

150. What is the best thing about your life right now?

random questions to ask anyone best thing in life

You might also like: Thought-provoking questions

151. What in life brings you the most joy and happiness?

152. What policies from the opposition political party do you agree with?

153. What’s your outlook on life?

154. Do you care what people think of you?

155. What holds you back from achieving your goals?

156. What has been the most spiritual moment in your life?

157. What lesson did you most recently learn?

158. What are your thoughts on fate?

159. What was the last tough decision you made?

160. If you could ask your future self anything, what would it be?

161. What has been your most humbling moment?

162. What food do you always crave?

163. Would you sacrifice yourself for a stranger?

164. What memory always has the power to cheer you up when you think of it?

165. What book made you into a better person?

166. What animal do you think will be the next to go extinct?

167. Do you believe there is life on other planets?

168. What skill would you most like to improve?

169. What makes you feel loved in life?

170. Would you ever take someone back if they cheated on you?

171. How does someone lose your trust?

172. Do you think karma exists?

173. Have you ever experienced DeJa’Vu?

Funny Random Questions To Ask Your Friends

174. Would you rather own a motorboat or a speedboat?

175. What animal would you like to shrink to the size of an ant and keep as a pet?

random questions to ask anyone tiny animal

Next: Good questions to ask

176. What is something that is in fashion now that in 10 years will be highly embarrassing?

177. What was the worst way you ended a relationship?

178. If you had to make a cashier laugh at check out, what three items would you buy?

179. What is something that you have refused to share with anyone until now?

180. What is your most embarrassing moment as a child?

181. What piece of clothing from Michael Jackson’s collection do you think you could pull off the most?

182. What dance move do you always fall back on if all else fails in the club?

183. If animals could talk, which animal would be the most annoying?

184. What’s the strangest piece thing you’ve ever seen in someone’s home?

185. Which animal would not be missed if it went extinct?

186. What’s the scariest movie you’ve ever watched?

187. If you could breed any two animals together and be guaranteed offspring, which animals would you choose?

188. If you had the power to ban one tv series currently on now, which would it be and why?

189. Have you ever felt uncomfortable wearing something in public? If so, what was the piece of clothing?

190. If you could shrink any household item and carry it in your pocket at all times, what would it be and why?

191. What is the most pointless fact you know?

192. What are the most awkward/embarrassing things to buy from the supermarket?

193. If you were a stand-up comedian, what would be your opening joke?

194. How many pigeons would it take to kill a lion?

195. Where has been the strangest place you’ve urinated in public?

196. If you could choose an alternative to hands, what would you pick?

197. For $1000, would you go on TV naked?

198. What’s the best pre-night out drinking game and why?

199. If you could have plastic surgery to enlarge one part of your body, what would you choose and why?

200. What’s the worst thing you’ve ever found in your food?

Looking For More Questions?

Questions to get to know someone – A more conventional list of questions to find out more about someone.

Open-ended questions – If you want to have a longer and more introspective conversation, these questions will do the trick.

Yes or no questions – Questions that can be answered either with a yes or a no. Ideal if you want to get to know someone quickly.

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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.