101 Flirty Questions To Ask A Guy

Have you ever tried to flirt with your crush, but found yourself tongue-tied? Or maybe you’re looking for ways to get to know your boyfriend a little better?

Either way, this list of flirty questions to ask guys will open up doors in your relationship, no matter what stage you’ve reached. 

Asking these questions can help you gain a deeper understanding of him as a person, while also developing your bond. Knowing him better will give you a new appreciation for his strengths and a better understanding of his point of view. 

The only downside is you’ll wonder why you didn’t read this sooner.

101 Flirty Questions to Ask a Guy

Ready to get started? Grab a pen and paper and write down your favorite questions.

Or better yet, print this entire article and keep it handy so you can surprise your guy with a new question every day.

Cute Flirty Questions to Ask Your Boyfriend

Just because he’s your boyfriend doesn’t mean you already know everything you need to know about him.

And these cute flirty questions to keep it light while you learn useful information about each other. 

1. When did you know you liked me? Where were we/What were we doing at the time?

2. What’s your idea of a perfect date? Where would we go? What would we do?

3. What is your love language?

4. What does love mean to you? How do you know someone loves you?

man and woman flirting outside flirty questions to ask a guy

5. What color do you think I look best in? What style of clothing?

6. What song would you compare our relationship to?

7. What was your favorite part of the day today?

8. Where do you feel safest? Is there a person you feel most comfortable with?

9. What was your first impression of me?

10. What’s your favorite activity to do to unwind or relax?

11. What’s your favorite memory that we shared?

12. What couples activity would you like to try? Ex: Couples yoga, crafting challenges, etc.

13. What three words would you use to describe me?

14. If we had to spend the day together in one place, where would we go?

15. Do you like using pet names? Are there any in particular that you prefer?

16. What’s your funniest childhood memory?

17. What’s one word that you’ve noticed me using excessively? Are there any words that you tend to overuse?

18. Name three things that never fail to make you smile.

19. What’s something you could talk about forever? What topic are you most passionate about?

20. Do you prefer kissing or hugging?

21. What’s the biggest deal-breaker in a relationship?

22. What’s your favorite mindless activity? Ex: Coloring, Watching TV, Reading, etc.

23. What’s your favorite grounding activity? Ex: Yoga, Meditation, etc.

Flirty Questions to Ask a Guy You Like

If you like this guy, and he’s willing to answer some questions, the following will give you a peek into the way his mind works — as well as whether he’s into you, too (though you might have to rely on body language for that). 

24. What’s your favorite TV or book couple?

25. What, in your opinion, is the best feel-good song?

26. Who knows you better than anyone?

27. If you could be a master of any one skill, what would it be?

28. What’s the nicest thing someone could say to you?

29. What accomplishment are you most proud of?

30. What’s something that not many people know about you?

31. Do you believe in love at first sight? Why or why not?

32. Do you prefer movie dates or restaurant dates?

33. What makes you laugh?

34. Do your friends have any nicknames for you? Do you like them, or would you like to change them?

35. Do you prefer a sweet breakfast or a savory one? What foods do you like to start your day with?

36. Do you like big romantic gestures or simple ones?

37. When something good happens, who’s the first person you want to tell?

38. If something bad happens, who do you confide in?

39. What’s your favorite kind of pie? Who makes the best?

40. Do you like to keep your birthday simple, or do you like to throw a party?

41. Do you like spicy food? What’s the spiciest thing you’ve ever tried?

42. How do you like your eggs? What foods do you like to combine them with?

couple laughing while lying on bed flirty questions to ask a guy

43. If you could be famous, what would you want to be famous for?

44. What was your favorite extracurricular activity in school?

45. What’s your zodiac sign? Does your personality reflect your sign?

46. What’s your favorite board game?

47. If you had $500 to spend on anything, what would you do?

48. Which fictional character do you most identify with?


More Related Articles:

77 Questions To Ask Your Significant Other For A Closer Connection

23 Signs A Guy Is Really Into You

29 Fun And Creative Long-Distance Date Ideas


Fun Flirty Questions to Ask a Guy

Picture yourself just having a fun conversation with a guy, and suddenly, your mind goes blank. And now he’s giving you that dreaded questioning look. That’s why it’s good to keep fun questions like the following handy.  

49. Are you a roller coaster person or a ferris wheel person?

50. If you could live in any fictional world, which would you choose?

51. What’s the craziest date you’ve ever been on?

52. If the world was ending tomorrow, what would you want to do today?

53. What do you consider to be your greatest skill?

54. What would you try if you knew you couldn’t fail?

55. What’s your dream vacation? How would you get there?

56. What’s on your bucket list?

57. Who would you want to be trapped in an escape room with?

58. Describe your life up to this moment in five words.

59. What’s the craziest dream you’ve ever had?

60. Do you like baking or cooking better?

61. Would you rather learn self-defense or gymnastics?

62. If you could learn any language, what would it be?

63. What was your favorite game to play as a child?

64. On Thanksgiving, what food are you most likely to go for first?

65. What’s the weirdest inside joke you’ve ever had?

66. What’s your preferred clothing style? Do you like to get all dressed up?

67. What’s your favorite candy bar?

couple laughing while holding ice cream flirty questions to ask a guy

68. Do you like to dance? Would you say you’re good at it?

69. What’s your favorite thing about the outdoors?

70. If you had to move to a foreign country, which would you choose?

71. If you could have any superpower, what would it be?

72. Who’s your favorite superhero?

73. What, in your opinion, is the most underrated song?

74. What story cliché do you actually like?

75. What’s an old movie that you think everyone should see?

Flirty Questions to Ask a Guy Over Text

You’ve met. You’ve hit it off. And now, you’re texting each other!

Congratulations for getting this far, but the flirty questions don’t have to wait for face-to-face time. Use the following questions to keep the flirtation going. 

 76. What three words would you use to describe yourself?

77. What’s your favorite emoji?

78. What’s your biggest pet peeve?

79. What’s your favorite season? Why?

80. Who do you look up to the most?

81. What’s your favorite ice cream flavor?

82. What’s your favorite holiday? How do you like to spend it?

83. What’s your favorite movie to watch with friends or company?

84. What’s your favorite feel-good movie for when you’re feeling down?

85. What’s your favorite holiday movie?

86. What’s your favorite thing to do at a party?

87. Who’s your favorite actor?

88. What’s your favorite song?

89. Where are you sitting and what are you wearing right now?

90. What emojis would you use to describe your day?

91. Will you send me a gif that captures your current mood?

92. Do you have any pets?

93. Do you prefer phone calls or texting?

94. If you could have anything for dinner, what would it be?

couple laughing while holding cups flirty questions to ask a guy

95. What does your name mean?

96. Will you send me a screenshot from your favorite show?

97. What’s your favorite social media site?

98. What app do you use the most?

99. Do you like dark chocolate or milk chocolate?

100. What’s your favorite kind of cheese?

101. Who was your first crush and why did you like her?

How will you use these flirty questions to ask a guy?

The guy you like will be blown away by your interest in his thoughts and perspective. 

With these flirty questions for him, you can gain a better understanding of the way his brain works, while also seeing the way he looks at the world. 

Of course, if he brushes off your questions and keeps dragging the conversation into safer territory (for him), that’s a definite red flag. 

But if he’s game, and he answers the questions to the best of his ability, there’s no telling what you’ll learn about each other — especially if he asks you to answer them, too.

This list will also give you some ideas for dates, gifts, or any simple gestures.

Make sure to keep this list on hand in case you need a way to deepen your connection.

May you both enjoy learning more about each other. 

Barrie Davenport
 

Barrie is a certified life coach and Wall Street Journal bestselling author. She has been a featured writer for The Huffington Post, Maria Shriver, and Zen Habits. She is the creator of six popular self-improvement courses. She writes books on relationship skills, emotional abuse, mindfulness, and more.

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