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150 Flirty Questions To Ask Your Crush

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These flirty questions to ask your crush will help you to get sparks flying between you and the person you’re attracted to. It can be hard to know what to ask someone you like, and even more so if you want to make the conversation a little flirty. That’s why we’ve curated this list of naughty questions to ask your crush.

They’re designed to be asked once you’ve got to know your crush and feel comfortable moving the topic towards a more spicy nature.

With many things to ask your crush relating to their desires, their past experiences, and some of their naughty fantasies, if the guy/girl is into you, you could be in for some spicy conversations!

Best Flirty Questions To Ask Your Crush

1. Tell me something that you’ve never told anyone? 

flirty questions to ask your crush tell me something you've not told someone before

2. What impression did you get when you first met me? 

3. What’s the first thing you notice about a person’s physical look when you meet them?

4. What physical feature do you usually notice first about someone?

5. What’s the best chat-up line someone has used on you? 

6. What qualities do you look for when you are dating someone?  

7. Do you have a favorite clothing color or style?

8. How would you let someone you have a crush on know you liked them? 

9. Do you have a favorite outfit for relaxing at home?

10. Describe your personality in three words? 


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11. What’s the most romantic thing you’ve done for a crush in the past? 

12. Do you enjoy spending time together in the same space?

13. Have you ever had an embarrassing moment you can laugh about now?

14. Would you rather be known as confident or intelligent?

15. What’s one quality you find especially attractive in people? 

16. What’s the most unusual daydream or goal you’ve had?

17. Are you a big cuddler? 

18. What type of things help you feel comfortable around someone? 

flirty questions to ask your crush what makes you feel comfortable

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19. Are you ticklish? 

20. What’s something strange you find attractive? 

21. What do you think is my best feature? 

22. Which love language do you identify with the most? 

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

24. If I invited you to hang out late one night, would you be up for it? 

25. Do you prefer coffee dates or heading out to a few bars?

26. Do you enjoy talking to me or hearing from me? 

27. Can I take you out on a date this weekend?

28. What’s the most unusual place you’ve ever been on a date or outing?

29. If we were to watch a movie together, what would you like to watch?

30. Do you have any favorite bars in town? 

31. How come you’ve been single for all this time? 

32. Do you have any favorite coffee spots in town right now?

33. How likely are you to want to carry on dating me? 

34. You look great in that profile picture, where was it taken?

35. What are the top five most essential things in your life currently? 

36. Do you have fears when it comes to dating? If so, what are they? 

flirty questions to ask your crush do you have dating fears

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37. What’s one thing people who know you would say about your love life? 

38. Do you think you give people a positive first impression? 

39. Is it essential for you to feel appreciated in a relationship? 

40. How would you describe me to someone? 

41. Are you someone who’s materialistic and likes high-value gifts? 

42. Do you have a close relationship with your family? 

43. Any plans for the weekend?

44. How important is celebrating special occasions like birthdays and Christmas? 

45. Has there ever been a situation where your opinion on girls or guys changed? 

46. Do you think that each human has their perfect partner out there? 

47. What’s the worst location I could take you on a date? 

48. Are you more playful or serious in a relationship? 

Fun Questions To Ask Your Crush

49. If you could go anywhere in the world with me, where would you go? 

50. Do you have a favorite way to unwind before sleeping? 

51. What would you least like to do for $1 million? 

52. What’s something you’re bad at that you wish you were good at? 

53. What’s the strangest compliment you’ve received from someone? 

54. What celebrity would you love to have a date with? 

flirty questions to ask your crush what celebrity would you date

55. What would your search history tell me about you? 

56. What color do you think I wear most often?

57. What always makes you smile? 

58. What guilty pleasures do you have? 

59. What do you think is the best thing about being in a relationship? 

60. What can you tell me about your first crush? 

61. Do you have a cute side? 

62. What would an ideal date look like to you? 

63. What do you like to do to de-stress? 

64. What are you passionate about? 

65. What’s the sweetest thing you’ve done for an ex-partner? 

66. Are you someone who actively goes and speaks to other people on a night out? 

67. Where on your body would you like to get a tattoo? What would it be of?

68. What’s not an attractive habit to have? 

69. Do you like sharing style opinions with a partner?

70. What’s something meaningful you’d like to experience in a relationship one day?

71. What are the most attractive qualities that someone can have? 

72. Do you enjoy close, comforting moments with people you care about? 

flirty questions to ask your crush do you enjoy cuddling

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73. Have you ever been mistaken for someone famous? 

74. What do you like about me? 

75. Have you ever tried online dating? 

76. Which language do you think is the most romantic?

Deep Questions To Ask Your Crush

77. What’s something about me that always sticks in your mind? 

78. What’s something most people don’t know about you?

79. Are you someone that people go to in a crisis? 

80. When was the last time you were in awe at something you saw?  

81. How have you dealt with heartbreak in the past? 

82. Is there anything that most people dislike that you don’t mind? 

83. If I were to take you for dinner this evening, what outfit would you wear? 

84. What’s your definition of a true gentleman?  

85. What’s your definition of a true lady? 

86. What are your thoughts on commitment in relationships? 

87. What are your weaknesses and positives?  

88. What book, TV series, or film had the most significant impact on your life? 

89. What does true beauty look like to you?  

Dirty Questions To Ask Your Crush

90. Do you prefer playful humor or serious conversations when flirting? 

91. Do you get your looks from your Mom or Dad?

92. Have you ever enjoyed playful texting with someone you like?

93. Have you ever wanted to invite someone over to spend more time together? 

94. Have you ever been on a memorable or awkward movie date? 

95. What are your thoughts on different relationship styles? 

96. Do you prefer cozy settings or bright, energetic environments?

97. Do you prefer spontaneous plans or carefully planned ones? 

98. How important is emotional connection on a first date? 

99. How do you know when a relationship is ready to move forward? 

100. Are you confident about your body? 

101. What do you think is one of my best qualities? 

102. What personal trait do people compliment you on most? 

103. What do you think helps a relationship succeed and grow? 

104. Have you ever questioned or explored what you’re attracted to? 

105. What’s the most adventurous thing you’ve done in a relationship? 

106. What color do you associate with me?

107. Do you enjoy playful teasing or light-hearted flirting? 

108. Do you have any fun hobbies or collectibles?  

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Freaky Questions To Ask Your Crush

109. How do you stay so attractive? 

110. Are there times when you find you’re attracted to the wrong/bad people?  

111. How can I get to know you better? 

112. How are you so good at just being you? 

113. Do you enjoy evening dates or daytime dates with an activity? 

114. What physical features do you look for in someone before dating them? 

115. What have you enjoyed most about the time we have spent together? 

116. What would your reaction be right now if I told you I had deep feelings for you? 

117. Would you try something adventurous with me? 

118. Do you work out every day to look that beautiful? 

119. If I told you how I really feel about you, how would you react?  

120. Take me on your ideal date?  

121. How long do you take to get ready before a night out? 

122. If we spent a whole day together, how would you start it? 

123. Would you rather relax on the beach or hike and explore?  

124. Do you like guys who are forward and tell you exactly what they’re feeling? 

125. All couples have cute names for each other; what would you call me? 

126. How much do you enjoy massages?

127. Have you felt like this about someone you’ve just met before? 

128. Do you think you’re the most attractive and best catch out of all of your friends? 

129. What do you think people think about age gaps between adults in relationships?

130. Do you prefer playful affection or calm, comforting moments? 

131. What’s the best and worst first message you’ve received on a dating app?

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132. Have you ever done something silly as an adult for someone you liked?

133. Can you remember your first ever date? How was it? 

134. Do you think it’s ever ok to lie to your partner? 

135. If you could add anything to your life right now, what would it be? 

136. Do you think the universe wanted us to meet? 

137. What’s your star sign? 

138. What’s the most romantic movie scene, in your opinion? 

139. What’s something you’re desperate to ask me but you’re apprehensive about doing so? 

140. What’s your go-to flirting emoji? 

141. Are you a stubborn person? 

142. Do you think piercings look good on people?

143. Are you someone who’s sentimental?

144. What’s the best thing about spending quiet time with someone you trust?

145. How do you feel about having children one day? 

146. How about I take you out this weekend? 

147. What’s your survival guide for any relationship? 

148. Who was your first serious adult relationship?

149. Have you always been single? 

150. What has failure in past relationships taught you? 

Looking For More Questions?

Second date questions – If things go well with your crush, these are the questions you should ask on the next 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.

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