76 Flirty Questions To Ask A Guy To Keep Him Interested

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This blog post is all about flirty questions to ask a guy.

flirty questions to ask a guy

Hard as it always is, catching your guy’s eye was the easy part. But now that you’ve grabbed his attention, you’re wondering what you can do to hang onto it and move your relationship forward. So how do you find out more about him without ringing the alarm bells in his tiny male brain?

The answer is that you get serious…. about flirting, which is using playful banter to get the information you really need and want to know. Here are flirty questions to ask a guy to get you started on your quest towards a tighter and more satisfying relationship.

Fun And Flirty Questions To Ask A Guy

Let’s start with a little bit of gentle verbal foreplay. These are simple flirty questions to ask a guy and which will generally leave the door open for him to ask you back.

1. What’s your middle name? Every middle name comes with a story all its own.

2. Have you been working out? Deep down, everybody likes to talk about themselves so draw him out with this easy entree.

3. Should guys always make the first move? Flirting with him is actually the first move but he doesn’t realize it.

4. What’s your favorite pick-up line? Free pass, pal. Let’s hear it.

5. What’s the craziest thing you’ve ever done? You are about to see the real goofy guy inside that T-shirt.

6. What’s your favorite thing to eat in bed? Talk about a double entendre.

7. What 3 words would you use to describe yourself? Don’t ask unless you are prepared to respond in kind.

8. Do you look more like your mom’s or your dad’s side of the family? Sounds innocent enough but he can’t answer without spitting out a lot of valuable information about himself.

9. What weird food combination do you like? You might just meet your soul mate with this one question.

10. What’s the worst thing you ever bought? This always brings out the laughter on both sides.

11. What movie character reminds you of yourself? Only one way to prove it.

12. Beach or mountains? There’s a great leading question.

13. Name a song that you like but pretend to your friends that you don’t. Gives you something to hum while you creep under the covers.

14. Growing up, did you want to be an astronaut or a fireman? Be sure you find out why.

15. What’s your favorite book? If he gives you a blank stare, be afraid, very afraid.

Life Questions

The first group of questions are hardly flirtatious in themselves but are intended to get the conversation going and to make him feel at ease. Now is your chance to drill down a bit further. Here are more flirty questions to ask a guy that focuses more on life.

16. Did we first meet by chance or did you go out of your way? The answer is either very romantic or very flattering.

17. Am I your usual type? This will be answered with some form of prevarication but you’ll learn a lot about why he feels the need to say what he says.

18. What’s your biggest turn-off? An exchange of prisoners is in order.

19. Are you ticklish? Dying to get your hands on him? Now’s the perfect chance.

20. What are your favorite pet names? And no, we aren’t talking dogs and cats here.

21. When was the last time you felt really scared? Almost as good as seeing a spooky movie together.

22. What was the last thing you had to do that you didn’t want to do? He’s about to share a really private part of himself so be gentle.

23. If you could go anywhere in the world, where would it be? It better not be the Croquet Hall of Fame, unless he’s kidding.

24. If you found a hundred dollar bill on the floor right now, what would you do with it? You’d better have a Benjamin stashed in your bra just in case it’s something good.

25. Name the best compliment you ever got and was it really deserved? No participation trophies here.

26. Is there anything in your life you wish you could do over again? You might not want to hear the answer so use this one carefully.

27. If you could be a superhero, which one would it be? Calling your inner nerd.

28. Name your worst pet peeve. And take careful notes.

29. How do you think I see you? What do you think I expect you to be?

30. What’s the one thing in life you wish you’d done but never did? Regrets, I’ve had a few…

Intimate / Dirty Questions

dirty questions to ask a guy

Now we are getting down into the real meat of flirty behavior. This is where you wanted the conversation to go in the first place but jumping right in runs the risk of scaring off all the fish or turning them into instant piranhas. Here are some dirty questions to ask a guy.

31. What the farthest you ever went on a first date? Fast and furious, or slow and easy.

32. What is the wildest place you ever had sex? Care for a rerun?

33. Did you ever have a crush on one of your teachers? And what was she wearing.

34. What is your idea of the perfect dream date? Hint, hint, hint.

35. What color bed would you like to see me lying on? What looks good with “hot”?

36. Which do you prefer: short skirt or tight jeans? Or short shorts.

37. Are you a boob guy or a booty guy? Hey, they’re all boobs but you know that already.

38. Any tattoos I’ve never seen before? No, that isn’t your mother’s name underneath that skull.

39. Where’s your favorite place to be kissed? Not talking Milwaukee here.

40. Name the most romantic thing you ever did for somebody. Better be good.

41. Name the most romantic thing anybody ever did for you. Better not be good because you’ll have to top it.

42. What’s the longest you’ve ever been in love? Better be more than a week, bub.

43. If we had a pair of handcuffs, would they go on me or on you? Or on both of us.

44. What’s the easiest way to turn you on in a public place? Filed away for future reference.

45. Back seat of the car or out on the grass? Don’t wear anything white when you ask this.

Flirty Questions To Ask A Guy Over Text

questions to ask a guy over text

Flirty texts are all about making sure that he’s thinking of you and that he knows you’re thinking of him even though he isn’t here with you right now. Here are some questions to ask a guy over text.

46. If we were together right now, what would we be doing? Hard to answer in 140 characters.

47. What’s your favorite thing about today? It better be something involving a text.

48. Tell me something you’re too shy to talk about in person. Gonna be great or ewwww.

49. Close your eyes and think of me. What am I wearing? All good answers here.

50. I’m going to send you a picture of me. Cute or naughty? He’d better answer real quick.

51. If I put my hands under your shirt, where would yours be? No pockets allowed.

52. Guess what color my underwear is today? If he says, “Well, it’s Tuesday…” then you need to shake things up a bit.

53. About tonight, red or black lingerie? Count on it, he’s coming home early.

54. Name something we should learn to do together. He already knows how to gut a fish so you’re safe.

55. What do you like best about me? Use only sparingly.

56. If I was an emoji, which one would I be? Hey, we’re texting here.

57. If you were an emoji, which one would you be? Fair’s fair.

58. I’m thinking about when we’re together again. Not exactly a question.

59. What song reminds you of me? “She’s a maniac” is not allowed.

60. I can think of better things than texting each other. More of an invitation than a question.

Would You Rather Questions

Time to play a little Binary Option theory. Check out these flirty questions to ask your crush!

61. Would you rather I tore your shirt off or demurely unbuckled your belt?

62. Would you rather take my clothes off or have me strip down in front of you?

63. Would you rather order in Chinese or take me out to dinner?

64. Would you rather see me dress up as a maid or a nazi?

65. Would you rather have sex at night or in the morning?

66. Would you rather have me in front of the fireplace or in the shower?

67. Would you rather be tied up or blindfolded?

68. Would you rather we both take today off or work extra hard and take Friday off?

69. Would you rather have candles or a disco ball?

70. Would you rather do something special with a feather or with whipped cream?

71. Would you rather go to a concert or a dance club?

72. Would you rather ride horses or rent go-karts?

73. Would you rather go shopping with me or wait in the car?

74. Would you rather send flowers or chocolate if you were sorry?

75. Would you rather receive edible underwear or a pet raccoon if I was sorry?

And for the big bonus round…

76. Would you rather meet me for drinks after work or go without sex for the next month?

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