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140 Naughty and Flirty Questions To Ask A Guy

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

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These flirty questions to ask a guy are perfect to ask a guy you’re seeing or want to take things further with.

The aim of these questions is to start a conversation around topics that increase the sexual tension between the two of you. By using these flirty questions to ask a boy, you’re making it clear you’re interested in them.

How they respond will allow you to gauge whether the attraction is mutual and if you’re suited to one another. We have freaky questions to ask a guy, fun questions and some romantic ones too.

Check out the questions below and see where the conversations they start lead!

Best Flirty Questions To Ask A Guy

1. What’s something that I could tell you that would surprise you? 

flirty questions to ask a guy what's something i could tell you that would surprise you

2. What’s the first thing you notice about a girl when you first meet them?

3. Am I going to see you in the bars this weekend?

4. What do you think my best feature is?

5. After a long day at work, how could I help you relax?

6. Do you like it when the girl takes the lead in the relationship? 

7. Would you rather be good-looking or extremely smart? 

8. Do you know any cool spots in town to hang out and grab a coffee?

9. How do you usually let girls know you like them more than a friend? 

10. Have you ever dreamt of me? If so, what happened in the dream?  

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11. Would you rather I was naughty or nice on our date? 

12. Does your weekend plan involve seeing me?

13. What color of lingerie do you think I’d look hot in?

14. Would you ever consider being in a causal relationship? 

15. How many relationships have you been in before meeting me? 

16. Which part of a woman’s body do you like most?

17. Do you find older women attractive? 

flirty questions to ask a guy do you like older women

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18. What have you imagined doing with me that you’ve never done with anyone else? 

19. Do you always want to be a big spoon, or can we swap?  

20. What’s a temptation you can never resist? 

21. Have you been skinny dipping before? Would you like to try it with me?

22. How would a perfect night look like with me?

23. What’s your biggest turn on? 

24. Would you like me to kiss you all over your body?

25. What is it you like about me?

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

27. Do you like it when a girl comes up to you on a night out and asks for your number? 

28. Should I sleep wearing clothes tonight?

29. What would you love to see me wear?  

30. Are you someone that likes to stay in at the weekend or do you want to go out and party? 

31. What was your first impression of me? 

32. Has your impression of me changed since we first met? 

33. How many other girls do you have a crush on right now? 

34. Do you see yourself as someone confident and forward or shy and not wanting to take the lead?

flirty questions to ask a guy are you forward or shy

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35. If you were to plan a romantic date night for us, what would it look like? 

36. I’m looking for some cool bars to visit this weekend, do you know any?

37. Do you agree that guys should always make the first moves when it comes to initiating intimacy? 

38. What clothing do you like to sleep in?

39. Do you think you thoroughly let your guard down when you’re with me? 

40. What’s the funniest way that you’ve been asked out? 

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

42. Did you imagine me to be like how I am, now you know me better? 

43. What are your plans this week?

44. What’s something you would never do for $1 million? 

45. Are you going to be at the party tonight? 

46. What’s the naughtiest film you’ve ever seen?

47. Do your friends know you’re on a date with me right now? 

48. What qualities do you look for when you’re dating a girl?

49. If you could board a plane with me right now, where would you go? 

50. Do you have any secret fantasies?

51. What’s the most adventurous thing you’ve done? 

flirty questions to ask a guy what's the most adventurous thing you've done

Next: Random questions to ask a guy

52. Do you believe you could fall in love with someone at first sight? 

53. Have you ever dated two girls at the same time?  

54. Do you think you must be friends first to make a relationship work? 

55. I’ve got enough room in bed for a +1, are you going to join me?

56. What famous person do you have a crush on? 

57. What type of girl do you usually go for? 

58. What do you think are your best qualities? 

59. What’s your idea of the perfect date?  

60. Do you see yourself as someone more of an extrovert or introvert? 

61. What naughty thought about me keeps you up late at night?

62. Do you enjoy cuddling? 

63. What’s the bravest thing you’ve ever done?  

64. What’s your main love language when you’re dating someone?  

65. Apart from me, what else are you obsessed with now? 

66. What’s the best place you’ve been on a date? 

67. Do you have to work out a lot to get a body as good as yours? 

68. If we eventually took the next step and went on a date, how do you think it would go? 

flirty questions to ask a guy next stage of the relationship

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69. What’s your go-to flirty emoji? 

70. What types of workouts do you like doing? 

71. Do you like to give and receive messages? 

72. Have you got a double bed?  

73. When are you taking me out on that date? 

74. What are your guilty pleasures in life? 

75. What do you find repulsive? 

76. What’s the best compliment you’ve ever received from someone? 

77. What do you think are some cute things a girl could say to her partner?   

78. What kind of dates do you like? 

Flirty Romantic Questions To Ask A Guy

79. What do you think the most romantic thing you’ve done for someone is? 

80. What’s your love language? 

81. Do you let your family and friends’ opinions get in the way of your feelings in a relationship? 

82. Do you think about me before you go to sleep?

83. How has someone as great as you been single for all this time? 

84. Have you been in love before?

85. At what point in our relationship do you think you will let your walls down? 

flirty questions to ask a guy letting your walls  down

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86. How would your friends describe you in two words? 

87. Are you attracted more to people’s personalities or looks? 

88. Do you like to receive romantic gifts? 

89. What do you think about me when we’re not together? 

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

91. What can you remember about our first kiss?

92. What are you looking for in a girl? 

93. Do you have any crazy passions?  

94. What can make you easily flustered?  

95. What questions do you think all people should ask each other before they get into a relationship? 

96. Are you a giver or a receiver? 

97. When was the last time you had butterflies in a relationship? 

98. What qualities do you dislike in a girl? 

99. What do you enjoy doing in the morning? 

100. How would you seduce me? 

101. What do you think are the best things about being in a long-term relationship? 

102. Does it take you long to trust someone? 

flirty questions to ask a guy does it take you long to trust someone

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103. Have you talked about me to your friends yet? How did you describe me?

104. What’s the best relationship advice you’ve received from someone?  

Fun Flirty Questions To Ask A Guy

105. Do you like being surprised? 

106. How would you like me to surprise you? 

107. What’s the most reckless thing you’ve done for love? 

108. Do you like to see some aggression in the bedroom from a girl? 

109. Do you like it when a woman flirts with you? How does it make you feel?  

110. What gets you excited about our relationship?

111. Do I ever make it into your dreams at night? 

112. What could you never live without? 

113. Do you have anything that you are guilty about?

114. What gets you excited?  

115. What’s something not many people know about you that would surprise me?  

116. What always gets you out of a bad mood and into a good one?

117. What’s something that took your breath away? 

118. What makes you nervous? 

119. Where in the world would you like to go with me?  

flirty questions to ask a guy where would you like to go with me

Next: Kinky questions to ask

120. What were you like with the girls in school? 

121. Tell me what the most embarrassing thing to happen to you was?  

122. What did you think of our first kiss? 

123. What’s one thing you own that has a bizarre history to it? 

124. Where’s the craziest place you’ve had done it? 

125. Have you ever been caught in the nude accidentally?

126. What’s your biggest turn-off when it comes to girls?

127. What does the word foreplay mean to you? 

128. Would you watch a romantic movie with me? 

129. Would you ever get a tattoo with my name on it? 

130. What have you always wanted to be given for your birthday?  

131. What do you think defines you as a person?  

132. What are your top three things to do on the weekend?

133. If I had to say yes to everything you asked me, what questions would you ask?  

134. Do you like flirting?

135. How would you feel about dating a friend’s ex-partner?  

136. Do you and your friends talk about each other’s intimate lives?  

137. Do you like showing affection in public?  

138. Are you ticklish anywhere on your body?  

139. Where’s your happy place?  

140. Do you prefer a steam room or a hot tub?  

Looking For More Questions?

Dirty would you rather questions – A naughty set of questions that will lead to some spicy conversations.

Dirty most likely to questions – Find out what your partner, crush, or the guy you’re seeing really thinks of you.

Funny first date questions – Going on a date with a guy for the first time? Make him laugh with these hilarious questions!

Flirty questions to ask your crush – Take things to the next stage with your crush with these questions!

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.