58 Flirty Questions To Ask A Guy You’re Crushing On

woman sitting at home in chair holding phone and texting flirty questions to ask a guy

You’ve got a new crush! This is an exciting time filled with late night texting sessions, awkward moments, and lots of flirting. It’s the phase when you’re first getting to know each other better, which is super exciting, but can be equally as nerve-racking as you both feel each other out and explore your connection. 

One of the least anxiety-inducing ways to handle a new crush is by engaging him in a flirty conversation and have some fun with it. Here’s how to break the ice and bring on the heat at the same time with our top flirty questions to ask a guy! 

Fun, Flirty Questions to Ask a Guy You Like

  1. Where do you work to get that amazing body?
  2. What’s the best joke you’ve ever told?
  3. You have a great smile. Did you ever have braces or are you just dentally gifted?
  4. Do you prefer cuddling up or having a make-out session? 
  5. If we spooned, would you be the big spoon or the little spoon?
  6. Have you ever skinny dipped before?
  7. What do you like most about dating?
  8. Would you prefer a day at the beach or at the movies?
  9. What’s your favorite body part on a woman?
  10.  Where’s the kinkiest place you’ve had sex?
  11. What do you find attractive in a woman?
  12. What do you think is your sexiest feature?
  13. What is your idea of the perfect date?
  14. Do you want to go out with me this Friday?
  15. How are you still single?
  16. How would you describe yourself in three words?
  17. What’s the first thing you noticed about me?
  18. How would you describe me in three words?
  19. In what ways are you attracted to me?
  20. What meal would you cook for me?
  21. How did you get so handsome?
  22. What’s your stance on a woman making the first move?
  23. Do I make you nervous?
  24. What turns you on?
  25. If your house was on fire and you could only save one thing, what would it be?
  26. What clothes do you sleep in, or do you sleep naked?
  27. What was the last thing that made you cry and why?
  28. What makes you laugh the most?
  29. If you could commit one crime and not get caught, what would it be?
  30. How do you define love?
  31. What are you looking for in a relationship?
  32. Have you ever dreamed about me?
  33. Do I make you smile?
  34. What’s the most adventurous thing you’ve ever done…in bed?
  35. Who do you admire?
  36. What’s your favorite thing to do in the world?
  37. Where’s your favorite make-out spot?
  38. What do you like most about me?
  39. What’s your ultimate fantasy?
  40. What does your dream life look like?
  41. What’s your favorite memory?
  42. What’s your favorite TV show of all time?
  43. Do you think you can satisfy me?
  44. If you could have any superpower, what would it be?
  45. Are you going to ask me out or will I have to do the job for you?
  46. What are you dying to ask me?
  47. Do you have a secret?
  48. If we went out on a date, how would it go?
  49. So are you a romantic or a little naughty? Or both?
  50. Where do you like to be kissed?
  51. Where would you like to kiss me?
  52. How would you seduce me?
  53. What’s your favorite love song?
  54. What sexy scene from a movie would you like to recreate with me?
  55. Who would you want to be tied up to for 24 hours?
  56. Do you know that you make me smile?
  57. Boxers or briefs?
  58. Have you fantasized about me?

Next time that you’re not sure what to say to your new man crush, use a fun, flirty question to ask a guy and up your dating game! Depending on the type of conversation you want or the type of connection you’re building, there are more than a few here to choose from. Happy texting! 

Brianne Hogan

Freelance Writer

Brianne is a Canadian freelance writer who’s been writing about dating and relationships longer than any of her relationships. She applies a “do what I say, not do what I do” approach to her articles, and believes you can find Your Person mostly when you aren’t looking. So enjoy your life, and eat lots of cheese (at least that’s her motto). Her byline’s been featured on Thrillist, The Huffington Post, HelloGiggles, Elle Canada, Flare, Awesomeness TV, among others.

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