150 Random Questions to Ask Someone

Looking for easy ways to kick off a great conversation? These random questions are perfect for getting to know someone better, whether you’re meeting them for the first time or just want to learn more about a friend.

From funny and lighthearted to thought-provoking, these questions cover a little bit of everything. They’re great conversation starters to break the ice, keep things interesting, or even uncover surprising things about someone.

I hope you enjoy!

Fun & Random Questions

1. What’s the strangest food you’ve ever tried?

2. If you could have any superpower, what would it be?

3. What’s your guilty pleasure?

4. If you could travel anywhere right now, where would you go?

5. What’s your favorite childhood memory?

6. What’s the most embarrassing thing that’s ever happened to you?

7. If you could live in any fictional world, where would it be?

8. What’s the worst job you’ve ever had?

9. What’s one movie you could watch over and over again?

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

Deep & Thoughtful Questions

11. What’s something that always brings you joy?

12. What’s the most meaningful gift you’ve ever received?

13. If you could change one thing about the world, what would it be?

14. What’s one lesson life has taught you recently?

15. If you could go back in time, what advice would you give your younger self?

16. What’s one thing you’re really passionate about?

17. How do you want to be remembered?

18. What’s the hardest decision you’ve ever had to make?

19. Who has had the biggest influence on your life?

20. What’s something you’ve learned the hard way?

Personal Preferences

21. What’s your favorite type of music?

22. What’s your favorite book of all time?

23. Are you a morning person or a night owl?

24. What’s your favorite way to spend a day off?

25. What’s your favorite season and why?

26. Do you prefer coffee or tea?

27. What’s your dream vacation destination?

28. What’s your favorite way to relax after a long day?

29. Are you more of an introvert or an extrovert?

30. What’s your go-to comfort food?

Friendship & Relationships

31. What’s your definition of a true friend?

32. What’s your favorite memory of us together?

33. What qualities do you value most in a friend?

34. How do you handle conflict in friendships?

35. Have you ever had a friendship that changed you?

36. What’s something you’ve always wanted to tell me but haven’t?

37. What’s the most important thing in a friendship to you?

38. How do you maintain long-distance friendships?

39. What’s your favorite thing about our friendship?

40. What’s one way we could strengthen our friendship?

Light & Fun Questions

41. What’s your favorite meme right now?

42. If you could be any animal, what would you be?

43. What’s the craziest thing you’ve ever done for fun?

44. What’s your favorite holiday and why?

45. If you had to eat one food for the rest of your life, what would it be?

46. If you won the lottery tomorrow, what’s the first thing you would do?

47. What’s your favorite ice cream flavor?

48. If you could switch lives with any celebrity for a day, who would it be?

49. What’s the best prank you’ve ever pulled?

50. If you could have dinner with any historical figure, who would it be?

Creative & Hypothetical Questions

51. If you could be any character in a movie, who would you be?

52. What’s your idea of a perfect day?

53. If you could invent something, what would it be?

54. If you were stranded on a desert island, what three things would you want to have with you?

55. If you could have dinner with any fictional character, who would it be?

56. What would your superhero name be?

57. If you could time travel, where would you go?

58. If you could relive one moment in your life, what would it be?

59. What’s your dream job if money wasn’t a factor?

60. If you were a famous artist, what kind of art would you create?

Career & Ambitions

61. What’s your dream career?

62. What’s one thing you’d like to accomplish in the next year?

63. What’s one skill you’ve always wanted to learn?

64. If you could start your own business, what would it be?

65. What’s the best advice you’ve ever received about your career?

66. What’s one goal you’re currently working towards?

67. How do you define success?

68. What’s something you’re really proud of in your career?

69. What motivates you to work hard?

70. If you could switch careers without any challenges, what would you do?

Personal Growth

71. What’s something new you’ve learned recently?

72. What’s your biggest personal achievement?

73. What’s one thing you’d like to improve about yourself?

74. How do you handle stress?

75. What’s a fear you’ve overcome?

76. What’s your favorite way to practice self-care?

77. What’s one habit you’re trying to break?

78. What’s something you’ve always wanted to try but haven’t yet?

79. What’s the most difficult challenge you’ve faced in the past year?

80. What’s one thing that’s helped you grow as a person?

Fun Icebreakers

81. What’s your favorite TV show right now?

82. What’s the last movie you saw?

83. What’s your favorite thing to do on a rainy day?

84. What’s your favorite board game or card game?

85. What’s your favorite way to spend a weekend?

86. If you had to describe yourself in three words, what would they be?

87. What’s your favorite place in the world?

88. What’s your favorite emoji?

89. What’s your go-to karaoke song?

90. What’s your favorite snack?

Relationships & Love

91. What’s your idea of a perfect date?

92. What’s your love language?

93. What’s the best relationship advice you’ve ever received?

94. How do you know when you’re in love?

95. What’s the most important quality you look for in a partner?

96. What’s the best thing about being in love?

97. How do you handle disagreements in relationships?

98. What’s something you’ve learned from past relationships?

99. What’s the most romantic thing someone has ever done for you?

100. What’s your favorite romantic movie?

Life Experiences

101. What’s one adventure you’ll never forget?

102. What’s the most spontaneous thing you’ve ever done?

103. What’s something you want to cross off your bucket list?

104. What’s one place you want to visit before you die?

105. What’s the longest road trip you’ve ever taken?

106. Have you ever traveled solo?

107. What’s a life-changing experience you’ve had?

108. What’s the best trip you’ve ever been on?

109. What’s one moment you wish you could relive?

110. What’s the biggest risk you’ve ever taken?

Family & Childhood

111. What’s your favorite family tradition?

112. What’s one thing you’ve inherited from your parents?

113. What’s your favorite childhood game?

114. How would you describe your family in one word?

115. What’s a family recipe you love?

116. What’s one of your earliest memories?

117. What’s the best part about growing up in your hometown?

118. How do you stay connected with your family?

119. What’s your favorite holiday tradition growing up?

120. What’s one thing you admire about your family?

Personal Values

121. What’s your biggest value in life?

122. How do you stay true to yourself?

123. What’s one thing you believe everyone should experience?

124. What’s your biggest priority in life right now?

125. How do you handle setbacks?

126. What’s something you believe in that others might not?

127. What’s your biggest fear?

128. What’s the most important life lesson you’ve learned?

129. How do you define happiness?

130. What’s something you would never compromise on?

Random Fun Facts

131. What’s a random talent you have?

132. What’s your go-to fun fact about yourself?

133. What’s a hobby you’ve always wanted to try?

134. What’s something you’re really bad at?

135. What’s the most random skill you’ve picked up?

136. What’s your favorite random fact?

137. What’s something unusual about you that most people don’t know?

138. What’s your favorite trivia category?

139. What’s your weirdest habit?

140. What’s the most random thing you’ve Googled recently?

Future Plans

141. Where do you see yourself in five years?

142. What’s one thing you want to achieve before the end of the year?

143. What’s your biggest dream for the future?

144. What’s something you’re looking forward to?

145. If you could live anywhere, where would it be?

146. What’s one new thing you’d like to try in the future?

147. What’s your dream for retirement?

148. What’s something you hope to do in the next 10 years?

149. How do you envision your life in 20 years?

150. What’s one thing you’re excited about right now?

Conclusion

With these random questions, you’ll always have something up your sleeve to keep the conversation going. Whether you’re aiming for fun, deeper talks, or just passing the time, these are the perfect conversation starters to help you learn more and connect on a new level. So pull out a few of these questions next time you want to break the ice or dive deeper into getting to know someone!