100 Flirty [And Cute] Questions To Ask Your Boyfriend

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Flirty questions are fun and cute. They keep the relationship alive and full of banter without getting overly sexual.

Whenever you’re around your boyfriend, just pull out this list and have a great time together!

Table of Contents

1. Have you always liked me as more than a friend?

How has he always seen you? Has he known that he wanted to be your boyfriend from the moment he laid those soft eyes on you?

example of a girl asking her boyfriend flirty questions

2. Where do you like to kiss me the most, my cheek or my forehead?

Hopefully he isn’t just a lip boy.

3. Where do you like me to kiss you?

Does he like those neck kisses and bites as much as you do?

4. How would you describe our most perfect kiss?

Is it the same as yours? Or is his something you nearly forgot about?

5. Do you believe in love at first sight?

Or does he believe in lust at first site?


6. What were your first thoughts when you saw me?

Was he drawn to you like a magnet with your looks or did he think wow, this girl really lights up the room!

For any of my LGBT readers, check out my complete guide to getting a gay boyfriend!

7. What were your first thoughts when you talked to me?

Did he think you were funny, witty, intelligent, sweet, sarcastic?

But wait… I’m sure you’re the sweetest girl he’s ever met, so here are some other types questions you may need for other occasions:

  1. Questions to ask on a first date
  2. Deep questions to ask a guy
  3. Funny first date questions 
  4. Sexual questions to ask your boyfriend

But hey, if you’re dead set on finishing this article right now, just keep reading and come back to these later!

8. Kisses or cuddles?

Both, duh!

9. Do you ever get nervous around me?

Does he blush still when he talks to you about the serious things? Does he still try and impress you but at the same time feel totally himself around you?

10. Do I give you butterflies?

Do they swarm in his belly and make him giddy and full of life?

11. Would you like it if I got tattoos?

Does he like the classic and simple style or someone a little rough?

dirty-flirty questions can make a guy fall in love with you even more

12. Have you ever had a dream about me?

Did he travel with you across the globe? Have a family with you?

13. What does holding me feel like?

Chocolate chip pancakes with maple syrup running down the side? Pigs in a blanket?

14. What is your first thought in the morning when you wake up next to me?

Does he think about how lucky he is to have someone like you in his life?

15. If we got married where would you take me on the honeymoon?

Would he take you to the best beach in the world? Or a little cabin with the mountains surrounding you? Or somewhere with it all?

16. If I had to move far away would you follow me?

Is he a hopeless romantic? Risking it all for his love?

17. Do you think we are soulmates?

Or does he think all that is silliness?

18. Would you introduce me to your family?

Is he secretive about you or open about it all?

19. Why do you think we met? What’s the reason?

Does he believe that everything happens for a reason?

20. Do you remember what happened the day we met?

Does he have any idea or is his memory rubbish?

21. What made you want to be my boyfriend?

Is he going to name something about looks… or something far deeper?

22. Is there a song that makes you think of me? What it it?

Does he always hear one song on the radio or on his phone that makes him think of you?

23. Would you like to dance in the rain with me?

Does he go out of his way to make your life full of precious memories?


24. Do you like holding my hand in public?

How does he feel about PDA?

25. If you could describe me in three words what words would you use?

Notice if he names physical, mental, emotional or spiritual language.

26. What is your favorite nickname I use on you?

How does he feel about pet names? Too cheesy?

27. What is your favorite pet name to call me?

What does he like calling you? Something special or something generic like babe?

asking flirty questions over text will get you many dates with a guy you like

28. Do you like my body odor?

Does he think you smell like roses and all things sweet?

29. What is something I do unintentionally that you love?

Is it the way you scrunch your nose, or use your hands a certain way when you say something?

30. What is your favorite quirky trait of mine?

What is that off thing about you that he loves oh so dearly?

31. Have you ever written a song or a poem about me?

Is he a hidden creative?

32. Do you like when I text you?

Or is he more of an in person kind of guy?

Kind of a flirty question to ask over text as he may reply that he only likes pics of… you know what!

33. Does it make you sad to see me sad?

Does he truly feel? Does he lack empathy or have it?

34. Would you risk your life to save mine?

Is it you before him?

35. Do you think I’m cute?

Hopefully… that should be one of the reasons he is dating you…

36. Do you think I’m pretty?

Once again… hopefully he does.

37. Do you think I’m sexy?

If you like dirty-flirty type questions, this one is for you and of course he does, he’ll probably blush!

after asking a cute-flirty question, your boyfriend will sweep in to kiss you

38. Would you take me on a picnic date?

Under the stars he shall say.

39. When you’re alone do you think about me?

Or is he a what’s in front of me is what I think about type?

40 What’s your deepest secret?

How dark is his past?

41. Would you take me on a trip with you and your friends?

Are his compartmentalizing skills beyond what you can handle?

42. Do you get jealous when I talk to other guys?

A little jealousy is cute, a lot not so much!

43. Curvy girls or slim girls?

Hopefully whatever kind of girl you are.

44. Straight hair or curly hair?

Those blonde locks or that pin straight brown?

45. Hair up or down?

Half up, half down!

46. Makeup or no makeup?

Natural or made up?

47. Do you like napping with me?

Those cuddles though.

48. Do you like when we cook together?

Is he the chef or the sous chef?

49. Do you enjoy going to the gym with me?

Does he lift you while you’re there?

50. What is something you’re thankful for, other than me?

Cute cute cute. His family and friends.

51. What is one of your best talents?

Other than making girls like you fall for him…

52. How do you define love?

He should define it by how he feels about you.

53. What is one thing you truly fear?

Great flirty “truth or dare” type question!

If he picks truth, you’ll find out if it’s about not living life to it’s fullest or maybe he’s terrified of leaving you.

On the other hand, if he picks dare, tell him that he needs to kiss you hand in public like a nice, cute boy!

54. What do you want to do with me before we die?

What does he dream of doing with you in his final moments?

55. What color looks best on me?

Does he like you in a certain color best, to is he happy with any and all of them?

56. What is something that sets me apart from other people?

What do you do that makes you you for him?

57. What actress is my look-alike?

Does he see someone else who looks like you?

58. Do you like my outfit?

He loves it honey.

59. What is your favorite body part on me?

Does he like those long legs, or that round booty?

60. What is your favorite body part on yourself?

Does he like his arms? His muscles?

61. What is the kindest thing you have ever done?

How is his definition of kindness different than your own?

62. Would you consider us romantic or spontaneous?

Or is there a perfect mix of both?

63. Love or money?

If he says money honey, run!

64. Want to know a secret?

Tell him something sweet!

65. Did you ever have a teacher crush?

Did he ever fall for a teacher? They say you like the people who teach you the lessons!

66. What do you wear to sleep?

Is he naked?

67. What are you thinking about right now?

He is thinking about all the things you’re asking him!

68. Would you go to a nude beach with me?

He would indeed. Any man would.

69. Do you think you’re funny? Tell me a joke.

Is his funny actually funny though?

asking a flirty question is sometimes about letting your boyfriend amuse you

70. Are you a heart breaker or the heart broken?

Does he do the breaking up or is he the broken up?

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

Invisibility, x-ray vision, flying?

72. Would you rather spend a day at the beach with me or hiking a mountain?

Chill and relaxed or go go go?

73. Would you rather introduce me to your parents or your siblings?

Who is he most proud of?

74. Purple or green?

Random, but flirty nonetheless.

75. Would you rather be in the land of the midnight sun or the daytime moon?

24 hours of sun or moon?

76. How many pictures of me do you have on your phone?

Does he save all the selfies you send him?

77. How many pictures of us do you have?

Does he have any framed by his nightstand?

78. Are you ticklish?

Go for it, get him. Get the sides!

79. How did you get such a great smile?

Does he blush? Is it from the braces or naturally a 100 watt smile?

80. Would you rather be the big spoon to the little spoon?

To hold or to be held, that is the question…

81. What are you dying to ask me?

Is there anything he has been holding back?

82. Boxers or briefs?

Maybe commando!

83. Do you like the chase?

Is it in his bones, that natural hunter gatherer stuff? Or is he more evolved?

84. You know you drive me crazy, right?

He’ll do something crazy here, on cue.

85. Do you like it when I make the first move?

Does he sometimes like to be chased?


86. Do you like looking in the mirror?

How big is his ego? Do you stroke it?

87. Are you drawn more towards my looks or my personality?

Chances are your looks got his attention and your personality made him stay.

88. What is the craziest thing you have done for a girl?

Stayed, haha, joke’s on you!

89. If you could teleport us anywhere in the world where would it be?

This is one he has most likely thought of!

90. Do you like being single or with me more?

Obviously you, duh!

91. Do you have any regrets about your love life?

Is he happy with his past lovers and the lessons he has learned?

92. Would you make out with me in the library behind the bookshelves?

It’s hot. Brains and making out.


93. Who makes you happiest?

You do. Always you.

94. Are your parents as attractive as you?

Wait for him to pop out their picture.

95. Do you prefer the pool or the hot tub?

Anywhere with you.

96. Would you like to go in the sauna with me?

Naked sauna time is the way to go. Sweat out all those toxins.

97. Do you like to party? Big ones or small gatherings?

Is he happiest alone with you or in a group with you?

98. Does drinking make you frisky?

What does he want to do with you or to you when he drinks?


99. Are we the best couple?

And the cutest couple award goes to…

100. Would you like to make music together?

Music about each other with each other, nothing more romantic or intimate than that!


These are some flirty and fun questions to ask your partner that will light up their day and remind them why they’re so attracted to you in the first place. Monotony kills the passion, so come back to the innocent spark with these!

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About the author 

Coach Colt here, the founder of Dating Armory, your go-to source for no-nonsense, practical relationship advice. I'm a bisexual male in a same-sex open relationship and a researcher in sex, love, and relationships with 7+ years of experience. I specialize in helping both men and women navigate the crazy world of dating.

Don't miss my other guides packed with practical dating advice (no bullshit repeated Platitudes) and tons of real life examples:

My Top 57 First Date Ideas That Always Work (As a Dating Coach)

Are Coffee Dates Good? It (Kinda) Depends

17 Basic Coffee Date Tips (From a Dating Coach)

How to Get a Gay Boyfriend: 25 Tips That Work