Are you looking for a list of interesting questions you can use to flirt with your crush?

In this article, we have come up with the best deep questions to ask your crush over text or in person.

You can send them as a flirty text message, a conversation starter, or a pickup line for a guy or a girl.

If you are looking for sweet things to say to a crush or ways to upgrade your flirting game, we’ve got you covered.

Personal Questions to Ask Your Crush

1. What do you do when you are in a happy mood?

2. What do you do when you feel sad?

3. What happens when you are very mad at someone?

4. What do you feel you shouldn’t have done in your life?

5. What would you wish to do but haven’t found an opportunity?

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6. What is your biggest regret in life?

7. What movie would you consider your best ever?

8. What TV show do you often want not to miss?

9. What is your take on big parties vs. small in-house parties?

10. What age do you consider the best in your life?

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11. What age do you feel was the worst in your life?

12. What is the best year of your life?

13. What city in the world do you find irresistible?

14. What is your preference between countryside life vs. busy fast-paced city life?

15. What is your favorite song at the moment?

16. Who is your crush at the moment?

17. How much do you love news and current affairs updates?

18. Which section do you find yourself skipping to first in a newspaper?

19. Who would you like to be president (politician or non-politician) today?

20. What topics do you find most exciting in a discussion?

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21. What is your most frightening experience in life?

22. Where would you love to have your dinner date in town?

23. What is your most common deal-breaker when it comes to dating?

24. Do you believe in fate controlling the outcomes in our lives?

25. What is your take on karma? (You get what you do to others in equal measure on earth)

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26. What rules define your life and daily living?

27. What rules do you have about dating?

28. What is the best gift you have ever received for a birthday?

29. What is the funniest gift you have ever received in your life?

30. What words of kindness have someone ever told you when you needed them the most?

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31. What do you do on a free weekend?

32. What is your greatest fear right now?

33. Do you feel you are living your dream like you wanted when you were a child?

34. What compliment do you receive most often?

35. What do you find yourself spending money on without caring?

36. What type of people do you enjoy hanging with the most?

37. What is your take on religion?

38. What is love to you?

39. What is beauty to you?

40. What does being a good person mean to you?

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41. What do you feel most proud of in your life?

42. What does home mean to you?

43. Are you extroverted or more introverted?

44. What are your daily routines in life?

45. Which book would you suggest everyone read?

46. Do you think kindness should be applied to everyone or close friends only?

47. What is your worst character that you strongly wish to change?

48. What would you wish to achieve in this world before you die?

49. What motivates you to want to achieve your life goals?

50. When last did you feel awe? What happened?

Deep Questions to Ask Your Crush

If you are looking for deep, meaningful, and flirty questions to ask your crush to see if they like you, these questions should give you a headstart.

51. What kind of people in life don’t you have respect for?

52. What is your take on p#rn?

53. What is your take on sex before marriage?

54. Who do you often feel if had met them before, your life would be different?

55. What is your take on rebounds and second chances in general?

56. What is your take on beauty vs. brains when it comes to dating?

57. What is your preference between money vs. character when it comes to relationships and marriages?

58. What do people underrate about you?

59. What one thing don’t most people know about you?

60. What do you find strange that most people find normal?

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61. How do you define a best friend? Do you have one person you consider your best friend right now?

62. What do you often find irresistible in someone you already are attracted to?

63. What is your definition of a gentleman?

64. What is your definition of a lady?

65. What is the one lesson you have learned so far in life?

66. What is the number one lesson you have learned about friends?

67. Would you rather love someone or be loved instead?

68. What do you believe is a modern-day hoax in life that most people don’t see?

69. Would you love to live forever? Why?

70. Have you ever had a dream you wished to not wake up from? What was the dream about?

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71. What should your ideal date wear for a dinner date?

72. Have you ever had a heartbreak?

73. How is heartbreak different from disappointment for you?

74. What do you do when heartbroken to help you heal fast?

75. What do you like that most people find strange?

76. Do you have something that most people never believe about you when you tell them?

77. What is one thing most people don’t know well about you?

78. Who are you mostly being mistaken for?

79. What is your naughty secret?

80. Are you more of an outgoing or reserved person?

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81. Would you rather be known for being sexy or for being smart?

82. What was your first impression of me? Has anything changed since?

83. Who should make the first move between a guy and a lady?

84. Have you ever tried or thought of making the first move on someone you like?

85. What is the most beautiful place you’ve been to and wished to go to again?

86. How do you tell when you like someone as a friend vs. when you like them as more than a friend?

87. What will your parents be very surprised to learn about you?

88. What is the nicest I have ever said to you?

89. Have you ever been mistaken for something you are not? What was it and how did you go about it?

90. How do you deal with persons who intentionally piss you off?

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91. What is the one thing you have never told anyone in your life?

92. What is the lamest excuse you have ever given for not wanting to go out?

93. Have you ever fallen out of love? What happened?

94. What lessons have you learned from your past relationship(s)?

95. What is one thing people think you are that you are not?

96. What are the craziest pick-up lines someone has ever used on you?

97. Does your name have any specific meaning?

98. What is your imagination of a completely perfect relationship?

99. What will you go for between money and love?

100. How much do you like “funny questions to ask your crush”?

Questions to Ask Your Crush Over Text

Asked at the most appropriate time, these good flirty questions will allow you to get to know your crush better.

101. Would you rather date for money or for fame?

102. What is the craziest thing you’d wish to try out?

103. What are your thoughts about someone having a side chick?

104. If your best friend cheats, would you cover up for them?

105. What makes a good relationship go bad easily?

106. How do you know when it’s time to move on?

107. Is it a good idea for people to be asking about others’ body counts when starting to date?

108. What is the one thing you admire about your parent’s relationship?

109. Would you rather date a younger or older person?

110. What do you consider boring when it comes to bedroom matters?

111. How do you respond to a body count question?

112. What is the craziest adult movie you have ever watched?

113. Have you ever done it in someone’s house?

114. How often should a dating person make out?

115. What is sweeter between s#x and romance?

116. What is the craziest bedroom style you have thought of trying for a long time?

117. Have you ever thought of someone else while making out?

118. Who is the one person you are struggling to get out of your mind?

119. Should people take a break from relationships after a breakup?

120. Have you ever moved in with someone before?

121. What do you think about a lady proposing?

122. Is ghosting the best way to break up with someone?

123. Have you ever ghosted someone?

124. Would you rather talk dirty over a phone call or erotic chat over a text message?

125. Have had to choose between two people at one point in your life?

126. Have you ever regretted not letting someone know you like them?

127. What is your biggest regret when it comes to dating?

128. What are the most common lies guys easily fall for?

129. Who do you look up to for relationship advice?

130. What are some of the common lies girls easily fall for?

131. What is a deal-breaker for you when it comes to bedroom matters?

132. What you ever had an encounter with a bedroom bully?

133. What is your worst s#x encounter story?

134. What are your views on friends with benefits?

135. What are your views on the materialistic types of relationships?

136. What is your no go zone when it comes to bedroom matters?

137. What is your worst encounter with an STI, if any at all?

138. Do men cheat more than women?

139. What is your view on long-distance relationships?

140. Do you believe in the existence of soulmates?

141. Do women cheat more than men?

142. Would you rather drink or smoke?

143. Have you ever hooked up in a club?

144. How likely are you to date a bartender?

145. How long should normal s#x last?

146. What is the longest you have ever stayed without s#x?

147. How often should dating people make out?

148. Can people date without s#x?

149. What is the one addiction you are struggling with?

150. Have you ever smashed with your best friend’s partner?

151. Have you ever smashed with a married man?

152. Have you ever smashed with a married woman knowingly?

153. What are some of the common lies married people tell?

154. What are some of the things you keep on lying to yourself about?

155. Have you ever snatched your best friend’s partner?

156. What passes as betrayal in a relationship?

157. What is the clearest sign that he loves you?

158. How do you know if someone is flirting with you?

159. What are some of the necessary lies to tell in a relationship?

160. What is the clearest sign that she loves you?

There you have your truth questions to ask your crush.

The questions are short. You can simply copy and paste them into your messaging app and send them right away.

Looking forward to a smooth convo with him or her with no roadblocks? Try out these smooth questions to ask your crush guy.