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160 Flirty First Date Questions

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

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Flirty first date questions are a great way to find out more about your date. They’re useful at gauging whether there’s a spark between the two of you.

First dates can be nerve-wracking and you always want to make a good impression. That can lead you to play it safe and not ask some juicy first date questions.

But this is a mistake.

By asking some naughty first date questions you can get to know your date better. You’re also likely to get a hint of whether they’re interested in you or not.

If you ask some of these questions below you can get to know your date better, find out if they’re interested or not and have a whole lot of fun too!

Best Flirty First Date Questions

1.  What’s the most daring thing you’ve done on a first date in the past?

flirty first date question on what the most daring thing you've done on a first date in the past

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

3. When you first saw me, what attracted you most? 

4. What naughty secrets do you have if any? 

5. Have you ever done something embarrassing in public? 

6. How important is it for your partner to be kinky? 

7. What’s the strangest place you’ve been intimate with someone?

8. Do you have any unfulfilled fantasies?  

9. What’s the most shocking pickup line you’ve heard?

10. How would you describe a perfect first date?

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11. Have you ever kissed someone before on a first date? 

12. Do you like a planned kiss or one that comes out of nowhere? 

13. Did you get your good looks from your Mom or Dad?

14. If you could date any celebrity, who would it be? 

15. What do you think about casual flirting?

16. Is there anything that always turns you on?  

17. How do you show someone you’re into them? 

18. What signs do you look for to see whether someone is into you? 

19. What’s the first thing you notice when you meet someone on a first date? 

20. Do you think love, at first sight, is a real thing? 

flirty first date questions do you think love at first sight is real

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21. Do you think each person has a soulmate? 

22. What do you like/dislike about the dating scene? 

23. How do you find dating apps? 

24. What’s your funniest first date story? 

25. Do you believe everyone is destined to meet their true love?

26. Do you think the saying ‘opposites attract is true when it comes to dating? 

27. Are you someone that likes to use cheesy/cute nicknames for your partner? 

28. What do you think about public displays of affection? 

29. Do you think about what our first kiss will be like?

30. Are you someone that’s open to trying new things? 

31. What’s more important, deep emotional intimacy or physical intimacy?  

32. Do you want to go on a second date with me?  

33. Can you remember the first-ever date you went on? How did it go? 

34. Do you like flirting with people? 

35. Where can you see us both after this date? 

36. What’s the most romantic thing anyone has ever done for you? 

37. Can you name five things that always cheer you up when you’re down? 

38. How would you rate this date out of 10? 

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

40. What’s going through your mind right now during this date? 

flirty first date questions what's going through your mind on this date

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41. Do you think all your walls are down when it comes to meeting new people? 

42. Are you always this fun to be with?  

43. If your friends could describe you in 3 words, what would they say? 

44. What will you tell your family and friends about this date? 

45. What is your usual type when it comes to dating? 

46. Do you want to know a secret of mine? 

47. Are you someone that likes to party all night long or someone that wants to curl up on the sofa and watch Netflix? 

48. Shall we get out of here and go to a bar? 

49. If someone famous could play you in a movie about your life, what actor/actress would you choose? 

50. What have you learned from previous relationships? 

51. How would you describe yourself in one word? 

52. Do you ever get moody, or are you someone that’s always on a high? 

53. Have you been a good or bad girl this year? I’m asking for Santa! 

54. Do you like people that ask lots of questions?  

55. What did you find interesting about my dating profile? 

56. Where are the five top places you would like to travel with me? 

57. Do you think people around you class you as a hopeless romantic? 

58. When did you last get butterflies for someone? 

59. What do you think love is? Have you experienced it before? 

60. Have you ever been heartbroken, or have you always been the one to break hearts? 

flirty first date questions have you ever been heartbroken

Next: Flirty would you rather questions

61. Has anyone told you how attractive you are? 

62. What’s your biggest turn-on and biggest turn-off? 

63. Rank the three most essential things in your life right now? 

64. What’s the most fun you could have on a date? 

65. Do you think you’re an adventurous person? Are you feeling adventurous tonight? 

66. What’s your favorite thing to do for fun? 

67. Can I plan the date next time? 

68. Would you make the first move on a first date if you thought the other person would reciprocate? 

69. Do you like my flirting game? 

70. Knowing what you do now, would you still swipe right on me? 

71. What qualities do you find attractive in any potential partner? 

72. Are you someone that enjoys cuddling?  

73. What was your first kiss experience like?

74. Can you fit me into your busy schedule this weekend? 

75. Does anyone you know have a perfect relationship? If so, what makes it perfect? 

76. How would you react right now if I told you I liked you? 

77. What expectations did you have before coming on this date? 

78. Were you nervous about meeting me at all? 

Flirty First Date Questions To Ask A Guy

 79. Are you someone that classes themselves as an introvert or extrovert? 

80. What’s something that you’re really obsessed with right now? 

flirty first date questions what are you obsessed with

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81. If you could choose anywhere in the world, where would be the best place to take someone on a first date? 

82. How do you show someone you’re comfortable with them? 

83. In the past, do you think your parent’s opinions have got in the way of you finding love? 

84. What do you think is your best physical feature? 

85. What are your plans for the rest of your life? 

86. Do you think you’re a romantic person at heart? 

87. Do you think you have enough time to commit to a relationship right now? 

88. At what point in a relationship do your walls start to come down? 

89. Do you like girls that make grand gestures? 

90. What’s the most outrageous thing you’ve ever done? 

91. What gift could I get you that would make you instantly fall in love with me?  

92. What passions do you have? Do you think we could do them together?  

93. Do you always play hard to get?  

94. Where’s the strangest place you’ve ever met someone? 

95. When you have a stressful day at work, what do you like to do to relax at home? 

96. If you were to plan an entire day with me, how would it look? 

97. What are you really looking for now in your life? 

98. Has anyone told you what amazing eyes you have? 

99. What’s something you would never forgive someone for? 

100. What brings happiness and meaning to your life right now? 

flirty first date questions what brings happiness to your life

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101. Are you someone that changes their opinions quickly? 

102. What excites you about me? 

103. What’s your self-care routine? 

104. How do you make yourself look this good before you leave the house? 

105. Do you think your bed is big enough for both of us? 

106. How would you feel about me if my main group of friends were all guys? 

107. Are you someone that gets jealous easily? 

108. What movie do you wish your life could be more like? 

109. Are you a ticklish person? 

110. What traits in a person do you find repulsive? 

111. What would your cute nickname be for me? 

112. What situations tend to make you flustered? 

113. Do you have a celebrity crush right now? 

114. Do you like to receive all-over body massages? 

115. What’s the worst chat-up line you’ve ever used? 

116. Have you ever hit on a girl when their partner has been in the same room? 

117. What small things in life do you enjoy the most? 

118. Are you a sentimental person? 

119. What famous couple do you think we could be like? 

120. What’s more important to you, money or love? 

flirty first date questions what's more important money or love

Next: Dirty questions to ask a guy

121. Do you think you could see me as more than just a friend? 

122. Where’s your favorite place to be kissed on your body? 

123. Have you ever kissed someone mid-talking?  

124. Have you ever found yourself on a nudist beach? 

125. Have you been shy around me at all this evening? 

126. Do you find tattoos attractive?  

127. What do you usually wear to sleep in? 

128. How do you feel about being single for all this time? 

129. Do you like to send naughty messages to people? 

130. Would you feel comfortable sleeping next to me? 

131. Have you ever been caught naked in public before? 

Flirty First Date Questions To Ask A Girl

132. You don’t have a crazy ex-boyfriend, do you? 

133. Do you think men are intimidated by you? 

134. What’s your favorite drink? 

135. Can I see you again and get to know you more? 

136. Do you like trying new things, or are you someone that likes to stick to familiar things? 

137. If you could be a man for the day, what would you do? 

138. Do you find yourself being attracted to bad guys or good guys usually? 

139. What does the perfect male body look like in your eyes? 

140. If you could ask me anything right now without me judging you, what would you ask? 

flirty first date questions what would you ask me if you could ask me anything

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141. Be honest, do you go for people based on looks or personality? 

142. If tonight was your last night on earth, how would you spend it with me? 

143. Are you someone that gets hung up on past events, or are you always looking to the future? 

144. Did you think about calling this date off this evening? 

145. What song best describes you, do you think? 

146. What’s your go-to flirty emoji? 

147. You look so amazing. Where did you get your outfit from? 

148. Do you like receiving compliments from guys? 

149. Do you have any hidden talents? 

150. What’s something unusual you find attractive in people? 

151. Do you think people’s first impressions of you are usually correct? 

152. What’s your favorite meal to cook for someone you like? 

153. Would you prefer me to call or text you going forward after our date? 

154. Have you got any cool playlists you can share with me? 

155. What’s been the highlight of your day today? 

156. What accent do you find most attractive? 

157. If you had to guess my favorite drink, what would you think it was? 

158. What’s your biggest deal-breaker in any relationship you have? 

159. What would you pay any amount of money for? 

160. When it comes to meeting new people, do you follow your heart or your brain? 

Looking For More Questions?

Fun Date Ideas – Looking for some great ideas for your next date? We’ve got you covered!

Questions to ask your crush – If you’re on a first date with your crush, here are some useful questions you can ask them.

Dating icebreaker questions – Some useful questions to ask your date if you feel the conversation is falling flat.

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.