150 Freaky & Flirty Questions to Ask Your Crush

Asking boring questions will lead to boring conversations, so why not have some fun with your crush instead?

One of the easiest ways to build chemistry with your crush and get to know them along the way is to ask them more intimate and suggestive questions.

The ideas that we will share with you will work best if you are already very comfortable with your crush and you want to take things to the next level.

You can ask these questions either in person when hanging out alone at the bar or by texting them to your crush at night when they are not busy.

However, keep in mind that the examples below are not ideal for someone you just met.

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It is important to build some rapport and comfort with a person before they will be ready to open up and talk about these intimate topics.

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Examples of Freaky and Dirty Questions to Ask Your Crush

Examples of Freaky and Dirty Questions to Ask Your Crush

1. What is something you would be really embarrassed to get caught doing?

2. What’s the most embarrassing thing that’s ever happened to you in a bedroom?

3. What is your favorite type of cuddling?

4. How many times you’ve done it in a day?

5. What’s the craziest thing you would be willing to do in a bedroom?

6. What is your favorite part of a woman’s body?

7. If you could describe my body with one word, what would it be?

8. Do you like to be spanked?

9. Do you like to be submissive or dominant?

10. What’s your favorite type of underwear?

11. Do you have any fantasies you’d like to try?

12. How do you feel about cuddling?

13. What is your favorite thing to do in the bedroom?

14. Do you like using protection or do you like raw?

15. If I was in bed with you right now, what would you do?

16. When was the last time you made love with someone?

17. What is the hottest thing someone did to you?

18. Does my outfit turns you on?

19. What is something you are really shy about?

20. What do you think about the “friends with benefits” concept?

21. When is the last time you were in a long-term relationship?

22. How do you react when people refer to you as hot?

23. What’s your favorite part of a girl’s body?

24. What turns you on the most?

25. How many people have you slept with?

26. Did you ever do it while skinny dipping?

27. Do you think personality is important or is it just physical attraction?

28. Do you prefer flings or relationships?

29. What is your definition of dirty talking?

30. Do you like to experiment in a bedroom?

31. When was the last time you did it in front of the mirror?

32. How would you rate yourself as a lover?

33. What do you do if you showed up to meet your blind date and you are completely turned off by them?

34. Do you consider yourself a player?

35. What is the craziest thing you did to get someone’s attention?

36. How many people have you kissed before?

37. Have you ever dated more than one person at once?

38. What did you learn from your relationship with your ex?

39. Is it a turn-off if your date is fat?

40. Is it a turn-off if your date is poor?

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41. Do you like people with tattoos and piercings?

42. Have you ever had a crush on any one of your friends?

43. How ideal 🍆 should look?

44. Do you prefer to date older or younger women?

45. Which actress or actor would you sleep with?

46. Have you ever had a one-night stand?

47. Do you see yourself ever getting married and having children?

48. What is the ideal size for a man’s 🍆?

49. Do you prefer big or small 🍒?

50. Do you prefer long or short hair on a woman?

51. Would you sleep with a married woman?

52. What do you think about girls who wear short skirts?

53. How do you like your men?

54. What does your ideal woman look like?

55. How often do you go out to the bars to meet women?

56. If you had to change something about your body what would it be?

57. Which part of your body are you most self-conscious about?

58. What was your first intimate experience like?

59. When was the last time you touched yourself?

60. What is the best way to a woman’s heart?

61. What is the most memorable intimate experience that you have had?

62. Do you go to adult clubs?

63. Do you like waking up with someone else or alone?

64. What was the longest time you have ever waited to sleep with someone?

65. What would you do if we were stranded on an island?

66. How many relationships have you had?

67. How old were you when you had your first kiss?

68. What is the most romantic thing you have done for your past partners?

69. How many times per week do you like to do it?

70. What was the worst date you have ever been on?

71. What is the most expensive thing you have ever bought for your ex?

72. How would you feel if I got undressed right now?

73. Do you prefer to do it in the morning, afternoon, or night?

74. What do you do to keep things fresh in a relationship?

75. What is your favorite piece of underwear?

76. How old were you when you made love for the first time?

77. What is the best compliment a guy could give you?

78. Is it weird to make out with a person you just met?

79. What turns you on when you see someone from across the room?

80. What is your ideal romantic location?

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81. Is there anything that you refuse to do on a first date?

82. What is the craziest thing that happened to you while dating someone?

83. Do you like to kiss on the first date?

84. How long can you go without doing it?

85. What do you like to do when you are alone?

86. What’s the best and worst thing about being single?

87. Which part of your body can I touch without you getting turned on?

88. What is your idea of a perfect first date?

89. Do you like playing truth or dare?

90. How would you rate your intimate life?

91. How would you rate your kissing skills?

92. What’s the worst pick-up line you’ve heard?

93. What’s the funniest pick-up line you’ve heard?

94. What turns you on more: The first kiss or a great massage?

95. Who was your crush when you were in high school?

96. Would you describe me as attractive, hot, or beautiful?

97. Can you climax just from kissing?

98. If I were to kiss you right now, where will I start?

99. How excited are you right now on the scale from 1 to 10?

100. What was the first thing that turned you on about me?

101. Have you ever tried it with another couple?

102. What is the furthest you have gone with a girl or guy on a first date?

103. Have you ever been dumped?

104. Would you consider having an open relationship?

105. What are your thoughts on cheating?

106. What is the fastest you have ever gotten intimate with someone?

107. If we were together, what would we be doing?

108. What do you need to see in order for you to think that a woman is attractive?

109. Do you like to cuddle in bed when you sleep?

110. What is your favorite activity to do after making out?

111. Which part of my body do you like to see the most?

112. When choosing between love and lust, which one will win?

113. Is intimacy an important factor in a relationship? Why or why not?

114. What is your definition of a fling?

115. How good was your first time?

116. If you could be in any other person’s body, who would it be?

117. If you are on a date with me, what would we do next?

118. If you had to choose between an adult movie star and an exotic dancer who would you date?

119. How good are you in bed?

120. What is your favorite way to make love?

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121. How much money would it take for you to sleep with someone you are not attracted to?

122. What do you consider to be the best part of being in a relationship?

123. Do you like lap dances?

124. Is there anything that you want me to do but afraid to ask?

125. What do you think about when you are making out with someone?

126. Are you more comfortable in the bedroom with someone who is more dominant or more submissive?

127. If you had a chance to go back and change one thing in your dating life, what would it be?

128. Have you ever done it over the video call?

129. How would you feel if I told you that I am attracted both to men and women?

130. What is the most daring thing that you have ever done in a bedroom?

131. What would you do if we were skinny dipping right now?

132. Are there any fantasies that you have never been able to fulfill?

133. What was your longest lovemaking session?

134. What kind of underwear do you wear?

135. What color is your bra?

136. What is your favorite movie to watch when cuddling on a couch?

137. When you make love, do you prefer it to be gentle, passionate, or rough?

138. How long have you been single?

139. What are your weaknesses when it comes to women?

140. What is your favorite color of underwear?

141. Do you like doing it in a shower?

142. If I was a fruit, which fruit would I be?

143. If today was your last day, what would you want to do with me?

144. Do you think that the first time should be special or can it be just a quickie like in the movies?

145. What would you want me to wear in a bedroom?

146. Have you ever broken up with someone because of incompatibility in a bedroom?

147. How would you try to attract me if we met in a bar?

148. What would you do to me if I were at your place?

149. How do you feel about public displays of affection?

150. What is your favorite way to be kissed?

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