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169 Interesting First Date Questions To Ask Your Date

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

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First date questions are important to consider as what you ask the other person on a date has a bearing on how well it’s likely to go.

It’s important to remember that this list isn’t a one-stop shop for all the questions you should ask on a first date. The purpose of this list is to provide a range of first date conversation starters to help the date go smoothly.

Once you’ve done that, a natural conversation can develop as you respond to each other’s answers. Asking a series of random questions is a surefire way to annoy and confuse your date.

If there are a few lulls in the conversation, this is only natural. Everyone’s a little nervous when meeting someone for the first time, no more so than when you’re on a first date.

If this happens, you have a huge list of first date questions to fall back on should such a situation arise.

Don’t forget a conversation is a two-way street. As well as asking your own questions, don’t forget to elaborate on your own answers and ask follow-up questions too.

Best First Date Questions

While this is by no means the definitive list of the best questions to ask on a first date, these are some good questions to get you started.

Similar to Questions To Get To Know Someone, you want a few basic and more in-depth questions to start the conversation so you can learn more about the person opposite you.

1. How do you like to spend your free time?

2. Who’s your favorite musician?

3. What would be your perfect evening?

4. What are some things everyone should try at least once?

5. What hobbies would you like to get into if you had the time and money?

6. If you could live anywhere in the world where would it be?

7. What would be your dream job?

8. What was the last book you really enjoyed?

9. What’s your favorite type of cuisine?

10. Would you rather go on holiday near a beach or the mountains?

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11. What world issue do you care about the most?

12. Are you an early starter or more of a night owl?

13. Tell me 3 things you look for in a partner?

14. What’s the last TV show you binge-watched?

15. What are the top five things on your bucket list?

16. What hobbies are you really enjoying right now?

17. What topics are you most interested in at the moment?

18. What’s your earliest childhood memory?

First date questions childhood memory

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19. Where’s your family from, and do you have any siblings?

20. What are you best known for among your friends?

21. Which states would you most like to visit on vacation?

22. Is there anything in life that really annoys you?

23. How would your friends best describe you?

24. What kind of music are you into?

25. Where was the last place you went on vacation?

26. What food have you always wanted to try?

27. Have you had any embarrassing moments recently?

28. Do you like going to live music events?

29. If you could have three people, dead or alive, over for drinks, who would they be?

30. What would be your perfect morning routine?

Good Questions To Ask On A First Date

If you’re looking for some more great first date questions, this selection will allow you to keep the conversation ticking along as you look to get to know the other person.

Some of these are thought provoking questions, while others are more basic in nature. But they’re all designed to keep your date on track!

31. What’s your favorite meal to make from scratch?

32. Who was your crush growing up?

33. Are you more of a night owl or a morning person?

34. What do you think about comedy nights, are you into them?

35. What behaviors in someone are a deal-breaker for you when dating?

36. What’s the longest relationship you’ve been in?

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37. What’s one of your happiest moments this year?

38. Is there a place you’d consider ‘home’?

39. What topic could you talk about for hours without getting bored?

40. What’s your favorite Pixar film?

41. Are you into reading? What was the last book you read?

42. What app could you not live without?

43. Where is your favorite place near where you live?

44. What was the last TV series you binge-watched?

45. Can you tell me any random facts about yourself?

46. If you had all the money in the world, how would you fill your days instead of working?

47. Do you have any allergies?

48. What’s one topic you could talk about forever?

49. What would the perfect holiday look like to you?

50. Is there anything you’re interested in learning about or improving in the future?

51. What are your greatest strengths and your greatest weaknesses?

52. How did you and your best friends get to know each other?

53. What makes you different from other people?

54. What’s your favorite romantic movie?

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55. What are your top ten favorite movies?

56. Who’s your role model in life?

57. What’s your proudest moment?

58. What’s your favorite alcoholic drink?

59. Where would you love to travel to?

60. What’s your go-to song when you need a dance?

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

62. What surprising thing has happened to you this year?

63. What’s a talent not many people know you have?

64. What nickname did you have in school?

65. What pet would you love to have?

66. What’s your favorite hot drink?

67. What could you do every day and never get bored of it?

68. What’s the most fascinating fact you know?

69. Do you prefer being indoors or outdoors?

70. Would you ever volunteer, and if so what would you do?

71. If you only had one week to live, what would you do?

72. Would you rather collect things or memories?

73. Where is your family from?

74. Would you ever live in a different country?

Cheeky First Date Questions

75. Where can our first weekend away be?

first date questions weekend away

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76. What nicknames do you have from when you were younger?

77. What’s the most ridiculous thing you’ve done because you were bored?

78. What’s your go-to funny story?

79. Where do you think this date is going?

80. Do you think emotional intimacy is important for physical intimacy?

81. What was the worst relationship you’ve been in?

82. What do you find attractive about me?

83. Do you have any dating horror stories?

84. If you were a porn star, what would your porn star name be?

85. What’s the cheesiest pickup line you have ever used or heard of?

86. What’s your love language?

87. What’s your best chat-up line?

88. Do you think opposites attract when it comes to dating?

89. What weird fetishes do you have?

90. What’s the craziest thing you’ve done for love?

91. Do you think love, at first sight, is possible?

92. How do you know that someone’s into you?

93. If you were in a karaoke bar, what would be your song of choice?

94. Tell me a fantasy you have?

95. What do you think about a girl making the first move?

96. If you could spend a day as the opposite sex, what would you do?

97. What would you do with the additional hours in the day if you didn’t have to sleep?

98. Have you ever kissed on your first date?

99. Do you have a dirty secret?

Funny First Date Questions

These questions are great to use at any point and can lighten the mood and strip away any tension either of you might feel.

First dates can be nerve-wracking, and similar to what if questions, these questions will allow you to discuss some irreverent talking points which will reveal more than you might realize about your date.

100. What’s your best joke?

first date questions joke

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101. What movie could you watch repeatedly and never get bored?

102. If there was a competition for everyday activities, what would you have a good chance of winning?

103. What’s the worst joke you’ve ever heard?

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

105. What’s the longest you’ve ever slept for?

106. Does your star sign match your personality?

107. What’s been the most significant plot twist in your own life?

108. What’s the weirdest place you’ve ever been to?

109. What makes a date fun in your eyes?

110. Will you swipe left or right on me after this date?

111. What animal do you think you could have been in your past life?

first date qusetions past life animal

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112. What fad did you never really understand?

113. What machine or appliance in your house frustrates you the greatest?

114. What’s the most embarrassing injury you’ve had?

115. What’s the funniest chat up line someone has used on you?

116. What are your thoughts on ghosts?

117. What do you think makes a good first date?

118. What’s happening today, that in 30 years people will look back on and find hilarious?

119. What’s your go-to hangover food?

120. What are your thoughts on pineapple on a pizza?

121. If you could only use only one Harry Potter spell, which one would you choose?

122. What’s your strangest quirk?

123. What would your friends think of me?

124. What’s something you’ve tried, but will never do again?

125. What’s your most useless talent?

126. Have you ever had to leave a date early? If so, how did you do it?

First date questions bad first date

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127. What’s the most hilarious/crazy thing you’ve ever done?

128. If you had to spend 10 days wearing the same pair of clothes, what would you wear?

130. Do you think that cats are secretly out to get us?

129. What’s the weirdest thing you’ve ever eaten and liked?

131. What’s the most embarrassing thing you’ve Googled?

132. If there were a zombie apocalypse tomorrow, what would you do? 

133. If you didn’t know my name, what would you call me?

134. What was the longest time you have ever waited to pick up some food that you’ve dropped on the floor?

135. What sports would be funniest if the athletes had to be drunk while playing?

136. What’s the most embarrassing thing that happened to you in school?

137. What would make an excellent ice cream flavor?

138. Are eyebrows considered facial hair?

139. What animated character would you date if you had to choose?

140. If Cinderella’s shoe fit perfectly, why did it fall off?

141. Have you ever sent a text to the wrong person?

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142. What background track would you choose if you were about to get into a fight?

143. What would your DJ name be?

144. Have you ever pulled any good pranks?

145. When was the last time you were in the hospital?

146. Which celebrity do you wish was your BFF?

147. Have you ever drunk texted someone?

148. What accent can you mimic?

149. What’s the silliest fear you have?

150. What’s the most embarrassing way you’ve been injured?

151. What’s the last thing you did that took you out of your comfort zone?

152. Do you believe in regrets and do you have any?

153. What pets have you had?

154. What are your favorite restaurants in the area?

155. What would you do if you won $10 million?

156. Who’s the most famous person you’ve met?

157. What’s your favorite movie?

158. Who’s your favorite author?

159. If a movie was made about your life, which actor/actress would play you?

160. What’s your most memorable family holiday?

161. What’s your favorite way to unwind?

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162. What sports did you play when you were younger?

163. What book do you think would make a great movie?

164. Which wild animal do you think is the cutest?

165. Do you have any phobias?

166. What’s the best gift you’ve ever received?

167. What’s your favorite sports team?

168. What wrong assumptions do people make about you?

169. What city have you always wanted to visit?

Looking For More Questions?

Flirty Snapchat questions – If you’re chatting with someone over Snapchat, here are some questions you can ask to spice up the conversation.

Flirty would you rather questions – A great game you can play to add an element of fun to any date!

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.