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100+ Random Questions To Ask People

Howard likes having interesting conversations with people and wants others to have them too.

Have your conversations gotten stagnant? Here are some random questions to ask people that could make things more interesting.

Remember that timing and selection are important when asking these questions. Not everyone wants to answer questions out of the blue, or ones that are personal or sound silly. Try to select the question based on how well you know someone and where in a conversation you are.

We've got so many questions here, the next one doesn't even count. Ready?


Random Questions

1. What's the best or worst dream you've ever had?

2. What's the strangest thing you've ever seen someone do?

3. What's the strangest looking thing you've ever done?

4. What's the strangest thing you've heard someone say?

5. What's the best thing you've ever smelled?

6. What's the worst thing you've ever tasted?

7. How do you picture yourself in old age?

8. What's the biggest change you've experienced in life?

9. What's the most beautiful place you've ever been?

10. What's the worst storm you've ever witnessed?

11. What country would you like to live in or retire to?

12. Would you go into space if you could, and why or why not?

13. If aliens came to earth, would you like to be the first to meet them?

14. If you could live in any time in the past, what would it be?

15. If you could jump 100 years into the future, would you go?

16. If you could instantly learn one language, which one would it be?

17. Would you trade 10 years of life for riches?

18. Would you accept a below average income for 10 more years of life?

19. How much money would you need to be set for life?

20. Is it possible to have too much money?

21. What would your dream home be like?

22. If you could be a success in any profession, what would you choose?

23. If you could instantly be a master of any skill or hobby, what would you pick?

24. What was your favorite subject in school?

25. If you had to relive one year of school, which would it be and why?

26. What's the most interesting building you've ever seen?

27. If you could make your living from a YouTube channel, what would it be about?

28. What invention amazes you the most?

29. Have you ever invented something or thought of something that should be invented?

30. Would you trade 25 IQ points for riches?

31. Would you accept a below average income for the rest of your life for 25 extra IQ points?

32. Who's the smartest person you've ever met?

33. Who's the most interesting person you've ever met?

34. If you had to live as an animal but with your brain, what would you be?

35. What's the most interesting animal? Insect?

36. If you could have an ability from any animal, what would you choose?

37. What's the scariest animal? Insect?

38. If you could change one thing about yourself, what would it be?

39. What's your favorite fruit?

40. If the moon was being colonized, would you like to go live there?

41. Would you give up your ability to feel pain?

42. Would you trade 25% of your muscle size to be 50% stronger?

43. If you could instantly play any instrument, what would you choose?

44. If you could automatically be an expert of any martial art, which would you choose?

45. If everyone in the world had to listen to you for one minute, what would you talk about?

46. If everyone in the world had to watch you for one minute, what would you do?

47. If you had to eat all your food from one fast food place for a week, which one would it be?

48. Is there any popular gadget or invention you would take away from everyone if you could?

49. What's the most stupid thing you've ever done?

50. What's the most stupid thing you've ever seen someone do?

51. What fictional family would you join if you could?

52. What do other people find hard that you find easy?

53. If you had to eat the same meal for a week, what would it be?

54. When you were a kid, what did you think you'd be when you grew up?

55. What would you most like to be famous for?

56. What's the most important thing for two people to have in common?

57. What household chore would you never do if you could?

58. What habit would you most like to break?

59. What habit would you most like to start?

60. What do people in general care too much about?

61. What do people in general care too little about?

62. Have you ever lent something you didn't get back?

63. What's the best lesson you've ever learned?

64. What's the most important thing to teach kids?

65. What quality do you like the most in others?

66. What's your best quality?

67. What's your worst quality?

68. Who is the most inspiring person you know or have heard of?

69. What's the funniest movie you've seen?

70. What is your earliest memory?

71. What is something you like but others usually don't?

72. What's your favorite song?

73. Do you think robots will ever be indistinguishable from humans?

74. Have you ever changed your mind about something you thought you'd always believe?

75. Do you have any phobias?

76. Are you unafraid of anything that scares other people?

77. What would you like your epitaph to say?

78. What's your favorite board game?

79. What were you afraid of as a child?

80. Do you collect anything?

81. If you had to commit a serious crime, what would it be?

82. If you were in the Guinness Book of World Records, what would you like it to be for?

83. What historical person would you like to have a conversation with?

84. What fictional character would you like to have a conversation with?

85. Has anyone ever thought you were a hero?

86. What heroic act would you most like to perform?

87. What was the best year of your life?

88. What was the first album or song you bought?

89. If you could remember everything you read in one day, what would you read?

90. What was your favorite toy as a child?

91. If you could spend the day with any celebrity, who would it be?

92. If you could safely have a wild animal as a pet, what would you choose?

93. Would you join a secret society?

94. What the worst name for a person you've ever heard?

95. Is there anything legal that should be illegal or vice versa?

96. Is there anything you used to do that you're now embarrassed by?

97. Would you like someone who had your exact personality?

98. If you were put into an insane asylum, how surprised would friends and acquaintances be?

Would You Rather Questions

99-111. Would you rather:

  • have high heat tolerance or high cold tolerance?
  • explore space or the oceans?
  • spend a day as a dog or cat?
  • have super hearing or super sight?
  • have enhanced taste or enhanced sense of smell?
  • be able to glide or breathe under water?
  • be 50% smarter or 50% funnier?
  • be able to fly or have super strength?
  • be an expert painter, sketcher or sculptor?
  • be an amazing singer or dancer?
  • be a great writer or a great speaker?
  • star in the most popular movie ever or most popular TV show ever?
  • be the writer of the most popular song ever or the singer?


Umesh Chandra Bhatt from Kharghar, Navi Mumbai, India on March 05, 2021:

Interesting compilation.

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