Dating crisis is real. These fun questions might save your next date

Let’s address the elephant in the room: we are currently in the middle of a dating crisis. Specifically, a crisis where many people have somehow forgotten how to ask questions on dates. And yes, it’s widespread. I’ve genuinely lost track of how many friends have recapped a date by saying, “It was fine, but they barely asked me anything about me.”

So if you’ve ever been hit with the classic, slightly awkward “So… is there anything you want to ask me?”, this list of fun date questions is absolutely for you. Honestly though, it’s for anyone who’s going on dates and actually wants to get to know the person sitting across from them. Which, let’s be real, is the entire reason dates exist in the first place.

Whether you’re on a FaceTime call, grabbing drinks, or taking a casual walk, first dates can feel nerve-wracking. But they’re also supposed to be fun. Having a few playful, engaging questions ready can ease the pressure, keep the conversation flowing, and help you genuinely enjoy yourself. The questions below were created with two goals in mind: helping you learn more about your date and giving you something to laugh about together.

Because humor is attractive. It builds connection fast. Dating expert Damona Hoffman, host of the Dates & Mates podcast, has said that laughter is one of the most powerful ways to bond and ease tension, whether you’re breaking the ice on an awkward first date or strengthening an existing relationship.

That said, you don’t need a perfectly rehearsed comedy routine. Dating coach Alexis Germany reminds us that being funny isn’t about trying too hard, it’s about trusting your natural sense of humor. Whether you’re into puns, dad jokes, or pop culture commentary, lean into what feels natural. Just don’t overdo it.

So without further ado, here are 200 fun, entertaining, sometimes unhinged questions to ask on your next date. Prepare for laughs, possibly the full-body kind.

200 Fun Questions to Ask on a Date

1. What’s the most basic thing about you?

2. What’s the most embarrassing song you secretly love?

3. What’s the funniest lyric you’ve ever misheard?

4. What kind of drunk are you—oversharer, emotional mess, or chaotic energy?

5. Which Taylor Swift era do you belong to?

6. According to astrology, what’s your worst trait that’s painfully accurate?

7. What’s your ultimate comfort food when you’re sad?

8. What’s the most unhinged thing you’ve done this year?

9. If you had to change your name, what would you pick?

10. If you could rename me, what name would you choose?

11. What condiment deserves to be banned forever?

12. What’s the weirdest social media challenge you’ve ever tried?

13. Who’s the most chaotic person in your family?

14. If you became famous, what would it be for?

15. What’s something you’re genuinely terrible at?

16. What’s something you hope your parents never find out?

17. Do you believe in ghosts?

18. Would you rather aliens or robots take over the world?

19. Which social media app should disappear?

20. If you got canceled, what would it be for?

21. What’s the cringiest thing you’ve ever posted online?

22. If you could start a rumor about yourself, what would it be?

23. What celebrity couple annoys you the most?

24. Which celebrity would actually make a good president?

25. Which celebrity would be the absolute worst president?

26. Where’s the worst possible place to get dumped?

27. What’s your go-to opening line on dating apps?

28. Do you believe rats secretly run cities?

29. If you could only listen to one song forever, what would it be?

30. Which celebrity couple do you think will break up next?

31. Who would you want to write your obituary?

32. Who would play you in a movie about your life?

33. Which The Office character are you?

34. What’s a TV show everyone has seen except you?

35. Astrology debate: Is Lana Del Rey a Cancer or a Gemini?

36. What genre would your life movie be?

37. Coke or Pepsi?

38. Who’s your problematic favorite celebrity?

39. Which horror movie stereotype would you be?

40. What sex position is overrated?

41. What sex position is underrated?

42. Which Sex and the City character are you?

43. If you were arrested, what would the charge be?

44. Who’s your celebrity hall pass?

45. Who’s your most niche celebrity crush?

46. What’s your favorite meme of all time?

47. What would your middle school crush think of you now?

48. Would you be friends with your middle school self?

49. Would you date your middle school crush today?

50. What’s the weirdest thing you do when you’re alone?

51. What’s the weirdest thing a roommate has caught you doing?

52. Are you a good liar?

53. What job are you unqualified for but confident you could handle?

54. What would your therapist say about you to their friends?

55. What would your boss say about you?

56. If you could live in another decade, which would it be?

57. Who’s the most overrated celebrity right now?

58. How would your third-grade teacher describe you?

59. What’s the dumbest thing you’ve cried over?

60. If you had to wear one Halloween costume forever, which would it be?

61. If you switched bodies with an ex for a day, what would you do first?

62. Have you ever been caught stalking someone online?

63. How often do you stalk your exes on social media?

64. Who was your first celebrity obsession?

65. If you were a cocktail, what would you be?

66. Which streaming service is essential—and which should die?

67. What’s the most embarrassing drunk moment you’ve had?

68. Would you rather be 15% hotter or 50% smarter?

69. What movie scene always makes you cry?

70. What’s your favorite excuse to cancel plans?

71. What emoji do you hate the most?

72. Which emoji describes you best?

73. How many tries did it take to pass your driver’s test?

74. What subject were you worst at in school?

75. What’s the cringiest dating app message you’ve received?

76. Are you a “sexy baby” or a “monster on the hill”?

77. Which Disney princess could you beat in a fight—and which would destroy you?

78. What was your pandemic hobby?

79. What was the last thing you Googled?

80. What’s something you learned way too late in life?

81. Would you rather reveal your porn history or food delivery history?

82. What would your presidential slogan be?

83. Who would be your VP?

84. Which historical figure would you want to be?

85. Which ex would you tolerate being stuck in an elevator with?

86. If you could relive one year of your life, which one?

87. Who’s your fictional crush?

88. Would you rather your mom or your crush see your search history?

89. What’s the worst dating app?

90. Have you ever been banned from one?

91. Kindle or physical books?

92. What was the first song you downloaded?

93. What was the most embarrassing song on your last Spotify Wrapped?

94. What would you name your signature perfume?

95. Taylor Swift, Beyoncé, or Rihanna?

96. Which of Henry VIII’s wives would you be?

97. What podcast would you love to guest on?

98. What yearbook superlative should you have won?

99. Which social platform do you use most?

100. What’s your most irrational fear?

101. What’s the longest you’ve gone without sleep?

102. Who would you swap lives with for a day?

103. Do you think anyone has you muted on Instagram?

104. Which Kardashian/Jenner life would you steal?

105. Which early-2000s reality show should come back?

106. Are reboots good or overdone?

107. What’s the weirdest rumor you’ve heard about yourself?

108. What was your worst first date?

109. Are you relieved or disappointed when plans get canceled?

110. What was the last lie you told?

111. Ice cream or pizza—pick one to give up.

112. Which millennial trend needs to die?

113. What’s the correct way to text “okay”?

114. What band deserves a reunion?

115. What’s the weirdest gift you’ve received?

116. What’s the weirdest gift you’ve given?

117. Have you ever crashed a wedding?

118. Whose wedding would you object at?

119. What was your funniest prank call?

120. What weird thing did you do for fun as a kid?

121. What’s your weirdest turn-on?

122. Caffeine or sugar—which could you quit?

123. Diet Coke or Coke Zero?

124. How long did your longest Monopoly game last?

125. What was your worst impulse purchase?

126. Which Mean Girls character were you in high school?

127. Has someone ever walked in on you?

128. What hygiene habit are you lazy about?

129. What do you lie to your doctor about?

130. What lie did you successfully tell your parents?

131. What’s the most trouble you got into as a kid?

132. What are you secretly a pick-me about?

133. What’s the best way to break up with someone?

134. Which dating app cliché annoys you most?

135. Would you wear your prom dress to your dream wedding?

136. What was the nerdiest thing about you growing up?

137. What’s the wildest thing you did to make someone jealous?

138. Where’s the strangest place you’ve hooked up?

139. What’s your go-to bagel order?

140. What’s the cringiest drink to order at a bar?

141. What sex myth did you believe as a kid?

142. What’s the most embarrassing song on your sex playlist?

143. What TV show can you quote endlessly?

144. Does pineapple belong on pizza?

145. If you could change zodiac signs, which would you pick?

146. Why are mirror selfies embarrassing in public but fine online?

147. What slang word needs to retire immediately?

148. Which celebrity do you irrationally dislike?

149. What would you name your Ben & Jerry’s flavor?

150. Would your favorite teacher be proud of you?

151. What’s the biggest lie you got away with?

152. What was your mom like at your age?

153. What’s your favorite first-date question?

154. What would your pen name or stage name be?

155. Who were you in a past life?

156. What’s your most controversial food opinion?

157. What’s your worst habit?

158. Where are you usually found at a party?

159. Are you a good wedding guest?

160. Who’s your dream plus-one?

161. What nickname would you give yourself?

162. What basic skill do you somehow lack?

163. What’s the most annoying gym behavior?

164. What show would you love to guest star on?

165. Would you let friends set you up?

166. What’s the theme song of your life?

167. What movie adaptation beat the book?

168. Five close friends or 1,000 followers?

169. What do your Spotify and Netflix say about you?

170. TikTok fame or a Grammy?

171. Grammy or Oscar?

172. Oscar or Emmy?

173. What’s your best dad joke?

174. What was the first R-rated movie you saw?

175. What word did you pronounce wrong forever?

176. Tell me about your best worst school photo.

177. What was your AIM screen name?

178. What awful middle school trend did you follow?

179. What do you overbuy constantly?

180. What pop-psych advice weirdly helped?

181. Influencer: dream job or nightmare?

182. Best WiFi name you’ve seen?

183. If you were a wrestler or superhero, what’s your name?

184. Go-to karaoke song?

185. What book do you pretend you’ve read?

186. What would your vanity license plate say?

187. How many hours a day are you on TikTok?

188. What’s embarrassing but shouldn’t be?

189. What kind of grocery shopper are you?

190. What’s the dumbest way you’ve hurt yourself?

191. What childhood belief lasted too long?

192. What’s the dumbest lie you told as a kid?

193. What’s something surprising about you?

194. Socks during sex—yes or no?

195. How long do you wait to pee during a good show?

196. What’s the grossest food thing you’ve done?

197. Have you ever been attracted to a cartoon character?

198. What would your memoir be called?

199. Is a hot dog a sandwich?

200. Be honest—what’s the question you hope people ask you on dates?