Fun Flirty Questions to Ask a Guy Or Your Boyfriend (Over Text or Face-to-Face) – Hot Topics He Can’t Resist

Flirty questions to ask guy

You might be wondering just how you get started conversing with a guy you like; especially if you feel he is the one.

We’ve got great flirtatious questions to ask this guy you have your eye on – they will add some fun and spice when you next chat.

They also take formality and strangeness out of the conversation. 

You feel you get to know your guy better, and the communication gets better, too – keeping you busy for hours.

You will soon discover how attractive a person he is, and he with you by asking him some flirty questions.

Because being an exciting person to each other is a crucial ingredient to a relationship, to begin with!

Even if you are going on your first date, our first question can get you chatting and discovering even more about each other.

You are set up for success with this list of spicy, flirty selections.

Some sound advice, though – don’t just barge into the first question and then continue down the list!

Remember that conversation is an art, and the questions laid out here are meant to build a relationship and not blow it up.

What Will I Learn?

Getting started

1) Find charming questions that you want to start with

Is this a guy you like and want to try and date?

Maybe this is a long-term boyfriend, and you want to have some fun with him!

So choose the right texts for the right stage of your relationship and the type of guy you are dating.

2) Setting the mood

That means the timing must be right. If you knew he was feeling down or ill, you could start with some cheering kind of messages.

Texts won’t work the right way if the timing ‘ain’t right.

If you are just a friend or in a brand new relationship, it won’t be the right time to get too personal – Some of those might scare him off a mile!

3) Just choose a few questions

There are plenty of great ideas from the list, but take it slow.

It shouldn’t feel like an interrogation of your boyfriend.

Read through the list and pick the questions you think would be fun for him.

4) Remember, it’s all about flirting

Keep things fun and light – these are flirty questions meant to build excitement, intrigue, and intimacy and bond you a little closer!

They are there to unpack as you go along – imagine all the lovely conversations for the future.

151 Cute Flirty Questions to Ask a Guy

Girl flirty with guy

1.“What’s your idea of a perfect date? A 5-star restaurant or a picnic on the beach?”

2. “What do you look for in a girl?”

3. “Are you an introvert or an extrovert?”

4. “How do you know if someone is amazing?”

5. “Are you obsessed with something right now?”

6. “Where is the best place to have a first date?”

7. “Have you been working out?”

8. “What’s the perfect way to ask someone out?”

9. “If we went on a date, how would it go?” Check out this video. It’s all about body language to turn a guy on. You will love it!

10. “What emoji do you usually use when you’re flirting?”

11. “What’s the most romantic thing you’ve ever done?”

12. “Do you feel comfortable with someone asking many questions?”

13. “Do you let your friends’ opinions get in the way of your relationships?”

14. “What do you think is your best feature?”

15. “What do you think is my best feature?”

16. “Are you aware of how amazing you are?”

17. “How did you manage to be still single?”

18. “Do you like staying in or going out?”

19. “What are you doing for the rest of your life?”

Want to get a bit more flirtatious?

20. “Are you a romantic person?”

21. “Do your weekend plans include me?”

22. “At what point in a relationship do you let your guard down?”

23. “Pick two words to describe yourself – what are they?”

24. “Are you more drawn to brains or looks?”

25. “Do you like grand gestures?”

26. “What’s the most outrageous thing you’ve done?”

27. “What gift would make you instantly fall in love with someone?”

28. “Do you have any passions? What do you love to do?”

29. “Where is the craziest place you have ever met someone?”

30. “When you return home after a long day at work, how would you want to relax?”

31. “If you could choose any place in the world you’d like to be right now, where would it be and why?”

32. “If you could spend an entire day with me, how would it look?”

33. “Who do you act nice around but secretly dislike?”

34. “What are you looking for in a girl?”

35. “Is there something I can do that would make you hate me forever?”

36. “What brings meaning to your life?”

37. “How often do you change your opinions or how you view the world?”

38. “What excites you?”

39. “When’s the last time you felt butterflies?”

40. How do you make sure you look good before stepping out the door?”

41. “Do you think people treat you differently when you dress in different clothes?”

42. “Do you flip your pillow to feel the colder side?”

43. “Would you feel different about me if I sleepwalk?”

44. “What movie do you wish your life was like?”

45. “If you could do anything in the world, what would you do?”

46. “Are you ticklish?”

47. “What kinds of things do you find repulsive?”

48. “What are your favorite pet names?”

49. “What makes you easily flustered?”

50. “Do you have a celebrity crush?”

51. “Do you feel good about massages?”

52. “Are you a fan of movies?”

53. “Where is your happy place?”

54. “Are you a fan of home-cooked meals?”

55. “Do you prefer a pool or a hot tub?”

56. “Would you rather be invisible or have x-ray vision?”

57. “What’s something you’re bad at? What’s your favorite thing about yourself?”

58. “What’s the worst pickup line you have ever used?

59. “What small pleasures do you enjoy the most?”

60. “Are you a sentimental kind of person?”

61. “How realistic do you think couples in movies and TV are?”

62. “Do you think that guys should always make the first move?”

63. “Between money and love, you would go for?”

Fun Flirty Questions

64. “Do you like me as a friend or something more?”

65. “Where is your favorite place to be kissed?”

66. “What would you do if I kissed you?”

67. “How would you describe your perfect kiss?”

68. “Do you prefer cuddling or kissing?”

69. “What is your biggest turn-off?”

70. “What did you think when you first saw me?”

71. “Do you believe in love at first sight?”

72. “Have you ever kissed someone in the middle of a conversation?”

73. “What was your first kiss like?”

74. “Is there ever a name you consider sexy?”

75. “Do you like it when the girl makes the first move, or would you rather be in control?”

76. “Would you ever go to a nude beach?”

77. “Do you ever get shy around me?”

78. “Do you find tattoos sexy? Have you got any?”

79. “What do you wear to sleep?”

80. “Have you ever had a dream about me?”

81. “How do you feel about being single for a long period?”

82. “What type of flirting do you prefer – via texts or face-to-face?”

83. “Do you feel comfortable sleeping beside someone?”

84. “Have you ever been caught naked by someone?”

85. “If you were swimming in public and lost your trunks, what would you do?”

86. “What was your very first impression of me?”

Now you are getting serious – time for some bigger conversations?

87. “If you could change one thing about yourself, what would it be and why?”

88. “Who was your first love?”

89. “Do you think you know what women want?”

90. “What do you value in a relationship?”

91. “Would you rather be called sexy or smart?”

92. “Do you ever cry when you are happy?”

93. “What’s the most romantic date you’ve ever been on?”

94. “What are your dreams and goals?”

95. “How would you define love?”

96. “Do you believe relationships can survive long distances?”

97. “Is there something crazy that you’ve ever dreamt of doing, but never got the chance to do it?”

98. “How long did your last relationship last?”

99. “How do you tell if you are already in love?”

100. “What does a happy and healthy relationship look like to you?”

101. “Does it bother you if you’re asked for your social media passwords?”

102. “Do you think your family would like me?”

103. “What’s the most embarrassing thing that’s ever happened to you when you were with a significant other?”

104. “How do you know that you just wasted time in a relationship?”

105. “What are some insecurities you have?”

106. “When are you the most “you”?”

107. “Are you willing to be someone’s shock absorber?”

108. “What has been a recurring theme in your life?”

109. “Has money ever been a problem in your past relationships?”

110. “Would you change your religion just to be with someone?”

111. “Do you consider yourself romantic?”

112. “Is there anything that happened in your childhood that still has an effect on you as an adult?”

113. “Is there one thing or secret that would surprise me about you?”

114. “Do you believe in destiny?”

115. “If there’s one thing you could change about yourself, what would it be and why?”

116. “Do you see me in your future?”

117. “What is your biggest regret about your love life so far?”

118. “Are you hopeful about your future?”

119. “How easily do you forgive?”

120. “What is something that scares you daily?”

121. “What’s the best relationship advice you’ve received?”

122. “What questions should partners ask each other before getting married?”

123. “What do you think is the right age to get married?”

124. “How important is it for individuals in a relationship to maintain their separate identities?”

125. “What kind of memories do you want to make together?”

126. “Do you think marriage is only a piece of paper?”

127. “Did you ever have a crush on a teacher?”

128. “What kind of outfit would you like to see me in?”

129. “Have you ever had a dream about me?”

130. “Do you like to be the dominant or submissive partner in a romantic relationship?”

131. “What excites you?”

132. “Do you want a picture of me looking cute or naughty?”

133. “Do you like it when a girl makes the first move?”

134. “Do you have hidden tattoos?”

135. “How do you feel about me not wearing underwear?”

The more erotic flirty questions

Leave the overly flirtatious conversation for when you and your boyfriend are beyond comfortable with each other – when there is true love between you two.

In the early stages, light, flirty questions are what you need to send.

It would be embarrassing if you just started dating to get in deep immediately.

But if you’re in a long-term relationship, here are some to spice up your conversations, but you probably knew them anyway!

136. “What would you do if I put my hands under your shirt?”

137. “Do you ever watch adult videos?”

138. “Can you send me a sexy pic of your favorite body part?”

139. “Can I watch you pleasure yourself?”

140. “Have you ever done it with more than one woman in one day?”

141. “What’s your favorite part of my body?”

142. “What’s your biggest fantasy?”

143. “Do you like it when I talk dirty?”

144. “Do you have dirty dreams about me, and what’s the craziest thing (sexually) you ever dreamed about?”

145. “Would you ever do it on the car?”

146. “Where do you want to touch me right now?”

147. “Do you prefer to give or receive?”

148. “Do you like getting oral?”

149. “What is the longest sex session you’ve ever had?”

150. “Have you ever gotten oral while driving?”

151. “Would you like me to do a striptease for you?”

Frequently Asked Questions (FAQs)

How do I get a guy to like me through text?

  • Show you like him through text.
  • Don’t demand answers straight away.
  • Know when to text.
  • Don’t text the guy you like when you’re drunk.
  • Send positive texts.
  • Start good conversations; never bombarding him.

If a guy likes me, will he text a lot?

Put it like this, he could want to text you a whole lot, but if he does like you, you can expect to hear from him around 3 times a day.

Actually, the more he likes you, the more he’ll text you.

How do I know he is interested in me or just being nice?

When he really looks at you, making eye contact, he likes you and is interested, but if he is just nice and he listens to you, he might be looking around at other things.


Do you have a mad crush on someone?

If you don’t like anything about your life at the moment because you are not getting the person you secretly love, maybe now is the time to think about some of the unbounded positives of life that are waiting just for you to start a new beginning.

And to do that, you need self-motivation and courage.

Start to recharge yourself for a brand new journey.

Remember this important quote, ‘be the one which you wish for’.

If you are deeply in love with someone, you can bring more smiles and joy to his face with some simple words that can be like a ray of sunshine to his world.

Here we have given you some wonderful flirty quotes to start with – Not the erotic ones!

But some friendly questions to your guy that might just take your journey where you never imagined possible!

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