150+ Fun Questions to Ask Anyone

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Use these fun questions to add a little spice, intrigue, and laughter into your conversations, and have a great time in the company of your family, friends, or partner – after all, there’s only so much you can talk about the weather!

Fun Questions to Ask

Fun Questions to Ask (list of questions 1-14 from the article).

For Friends

1. What is the first thing you would spend money on if you won the lottery? 

2. Do you believe in ghosts? 

3. What time period would you visit if you had a time machine? 

4. If your life had a theme song, what song would it be? 

5. If you could change your name, what would you change it to?

6. What is your least favorite food? 

7. What is one of your most embarrassing childhood memories? 

8. What have you always wanted to try but never gotten the chance to? 

9. What is your favorite thing that you own? 

10. What is your dream car? 

11. If you could live in a fictional universe, which universe would you choose? 

12. Sunset or sunrise? 

13. What is the most important quality you look for in a friend? 

14. What genre of music is your least favorite? 

15. What member of your family do you consider yourself closest to? 

16. Would you ever get a tattoo? What would it be? 

17. Do you consider yourself to have good handwriting? 

18. What is the silliest reason that you have ever cried?

19. What is or was your favorite subject in school? 

20. What is your signature dance move? 

21. Can money buy happiness? Why or why not? 

22. What is your funniest family tradition? 

23. If you could sleep all day, would you? 

24. What is one conspiracy theory that you believe in? 

To Get to Know Someone

25. If you could relive one moment in your life, what moment would you choose? 

26. Where have you always wanted to travel, and why? 

27. Are you a morning person or a night person?

28. How would you describe your personal sense of humor? 

29. Do you believe in aliens? 

30. What is one thing you like the most about yourself?

31. What is your favorite holiday?

32. What is something you wish you could tell your younger self? 

33. What is your favorite time of day?

34. What is the coolest place you’ve ever traveled to? 

35. What is your favorite hobby? 

36. What is something you collect? 

37. What season is your favorite? 

38. What is the weirdest thing you have ever eaten? 

39. What would the title of your autobiography be?

40. If you could go to any concert for free, what concert would it be? 

41. What is something that never fails to make you happy? 

42. What unreasonable fears do you have? 

43. Do you have a lucky number? If so, what is it? 

44. How would you describe your personal style? 

45. If you had to teach a class in something, what would it be? 

46. What was your most memorable birthday? 

For Coworkers

47. What is one of your favorite memories from work? 

48. Have you ever met a celebrity? Who? 

49. If you could change places with anyone in the world, who would you choose? 

50. What is your dream vacation? 

51. What is your favorite karaoke song? 

52. What reality television show would you like to star in? 

53. What is your biggest pet peeve? 

58. If you had your own podcast, who would you invite as your first guest star?

59. What is your hometown best known for? 

60. Do you prefer the city or the country? 

61. What is the number one thing on your bucket list?

62. If you were to become famous, what would it be for? 

63. What is your favorite tv show to binge? 

64. If you could become fluent in any language, which language would you choose? 

65. What is your hidden talent? 

66. What has been the best year of your life so far? 

67. Do you answer the phone or let it go to voicemail? 

68. What is the luckiest thing that has ever happened to you? 

69. Do you believe in karma? 

70. What is one food you will never try?

71. Would you consider yourself more of a follower or a leader? 

72. What is the longest amount of time you’ve gone without sleeping? 

For Your Partner

73. What is your first childhood memory? 

74. What is your favorite gift you have ever received? 

75. What is the best piece of advice you’ve ever gotten?

76. Have you ever been in a life-or-death situation? 

77. What is one thing you like the least about yourself? 

78. What is your personal definition of love? 

79. What is your all-time favorite movie? 

80. Do you have a guilty pleasure? If so, what is it? 

81. Do you believe that dreams have meanings? 

82. What nicknames do you have? Do you like them? 

83. What is a subject you wish you knew more about? 

84. What would you want to name your future children? 

85. What would you do if you woke up as the President of the United States? 

86. What color would you paint your dream house? 

87. What is the worst date you’ve ever been on? 

88. What celebrity or influencer do you most look up to? 

89. If you had a time machine, would you rather visit the future or visit the past? 

90. What is the best vacation you have ever been on? Why? 

91. Do you prefer listening to audiobooks or reading books? 

92. What is the funniest joke you know? 

93. What was the worst haircut you’ve ever had? 

94. If you had a weekend all to yourself, how would you want to spend your time? 

95. Do you believe in love at first sight?

96. Do you make decisions more with your heart or with your head? 

97. What is a time in your life when nothing went to plan, but you still had a good time? 

98. What was your first impression of me? 

99. What is your favorite memory of us? 

To Ask a Girl

100. What would your ideal weekend look like? 

101. What fashion trend do you absolutely hate? 

102. Would you ever dye your hair? If so, what color? 

103. If you could change one thing in the world right now, what would you change? 

104. What is an unpopular opinion you have? 

105. What is a moment in life that you are the proudest of? 

106. If you could ask your future self one question, what would it be? 

107. What is your favorite scent? 

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

109. What is a career that you would never consider for yourself? Why? 

110. Do you prefer white chocolate, milk chocolate, or dark chocolate?

111. If you had to move to a new country, what country would you choose? 

112. What actress would play the role of you in a movie about yourself?

113. What is the last dream you remember?

114. If you could master one skill, which skill would you choose? 

115. What is your favorite item in your wardrobe?

116. Who is your role model?  

117. Who was your childhood best friend? Are you still friends with them? 

118. What is the saddest movie you’ve ever seen? 

119. What is the best compliment you’ve ever received? 

120. If you could change your past, would you? If so, why? 

121. What color do you wear the least? What about the most? 

122. Do you prefer the mountains or the beach? 

123. If you could switch wardrobes with one celebrity, who would you choose? 

124. What do you wish more people would ask you about?

To Ask a Guy

125. What is one thing that most people don’t know about you? 

126. What is your dream job?

127. Are you a cat person or a dog person? 

128. If you could only eat one food for the rest of your life, what would it be? 

129. Who inspires you? 

130. Do you like rollercoasters? 

131. What is the one song that means the most to you? 

132. What is your funniest childhood memory? 

133. If you were a DJ, what would your DJ name be? 

134. What is a skill or hobby that you want to try? 

135. What is your favorite food to make? 

136. If you had to change your hair color, what color would you choose? 

137. What type of weather is your favorite? 

138. What is your favorite way to travel: by plane, train, or boat? 

139. What is one thing that you would like to be remembered for? 

140. If you had to choose one company to invest money into, which company would you choose? 

141. What is your favorite brand of shoes? 

142. Would you consider yourself a rule-breaker or a rule-follower? 

143. If you had to choose, what would be your last meal? 

144. If you could be good at any sport, which would you choose? 


145. If you could have any superpower, which power would you choose? 

146. What is your favorite dessert? 

147. What would you change about the world, if you could only change one thing? 

148. What is your favorite word? 

149. Have you ever built a snowman? Had a snowball fight? 

150. What is your favorite thing that you own? 

151. What do you think would make a good ice cream flavor? 

152. What is something that always makes you laugh? 

153. If you could make up a new holiday, what would it be?

154. What is something you are most afraid of? 

155. What is your favorite month of the year, and why? 

156. What is your favorite memory? 

157. Who do you look up to most in the world? Why? 

158. Do you prefer staying home or going somewhere new? 

159. What is your favorite song to dance to? 

Directing the conversation is all about the questions you ask, and if you want to keep things fun yet interesting, these 150+ questions are great to have in your back pocket.

Whether you’re on the sofa with your partner, catching up with an old friend, or getting to know a coworker, there’s always a place for fun, less serious conversation to keep a smile on everyone’s face.

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Keep these fun questions for safekeeping by saving this article to one of your conversation starter Pinterest boards.

Fun Questions to Ask (list of questions 1-14 from the article).