73 Flirty Questions to Ask a Guy That Will Make Him Smile, Blush, and Think About You

Flirting doesn’t have to be awkward or over-the-top. Sometimes, all it takes is the right question—something playful, curious, and just a little bit cheeky—to break the ice and get the sparks flying. If you’re looking for fun, flirty questions to ask a guy, whether you’re texting, chatting in person, or sliding into his DMs, these conversation starters will help you turn small talk into something a little more exciting.

Why Flirty Questions Work Better Than Cheesy Pick-Up Lines

Flirty questions are the perfect way to keep things light, fun, and intriguing without crossing any lines. Unlike canned pick-up lines, they feel personal and authentic, inviting him to open up while keeping the vibe playful and charming. They show that you’re confident, interested, and not afraid to add a little sass to the conversation. Plus, they give him a chance to flirt right back—win-win!

73 Flirty Questions to Ask a Guy (That Aren’t Too Obvious)

1. What’s something you think would make me blush if I knew?
2. If I dared you to kiss me right now, would you do it?
3. What’s the most romantic thing you’ve ever done?
4. Would you rather cuddle on the couch or go out for a late-night adventure?
5. What’s something you think is totally attractive but most people wouldn’t guess?
6. How do you know when someone is flirting with you?
7. What’s your go-to move when you like someone?
8. Would you rather go on a beach date or a rooftop dinner?
9. What do you notice first when you like someone?
10. Have you ever been caught checking someone out?
11. If we got stuck in an elevator together, what would you do to pass the time?
12. What’s the most unexpected thing someone could do to make you fall for them?
13. Are you the type to make the first move or wait for someone else?
14. Would you rather I send you a cute selfie or a mysterious text?
15. What song would you dedicate to me right now?
16. If we had to share a dessert, what would you pick?
17. What’s something about you that you think I’d find irresistible?
18. How would you rate yourself as a kisser—scale of 1 to 10?
19. Do you believe in love at first sight, or should I walk by again?
20. Would you rather I make the first move or let you take the lead?
21. What outfit do you secretly think would make me look extra cute?
22. What’s something totally innocent that drives you crazy (in a good way)?
23. If we had a bet and you lost, what flirty punishment would you be willing to accept?
24. What’s the one thing I could say right now that would make you blush?
25. Would you rather have a flirty dance battle or a slow dance under the stars?
26. When you dream about your ideal date, what’s the vibe?
27. What’s the cheesiest thing you secretly find romantic?
28. Would you rather go for a cozy blanket fort date or a moonlit walk?
29. What’s something you’d love for me to dare you to do right now?
30. How do you flirt when you’re crushing hard?
31. Would you rather I steal your hoodie or steal your heart?
32. What’s the best compliment you’ve ever gotten from someone you liked?
33. Would you rather cuddle in hoodies or dance in fancy outfits?
34. If I asked you to teach me something fun, what would it be?
35. What’s the most fun date idea you’ve ever had but never tried?
36. If I told you I was cold right now, what would you do?
37. Would you rather be called handsome or adorable?
38. What’s the most daring thing you’d do on a first date?
39. Would you rather get a flirty text from me during the day or a flirty goodnight message?
40. What’s your idea of a perfect kiss—spontaneous or planned?
41. If we had to do a couple’s costume, what would you suggest?
42. What’s something you wish girls knew about flirting with guys?
43. Would you rather spend a day at an amusement park or a night stargazing?
44. What’s your most “guilty pleasure” romantic movie or song?
45. Would you rather have me as your date for a fancy party or a chill game night?
46. How do you think I’d react if you whispered something sweet in my ear?
47. If I dared you to plan our dream date, what would you do?
48. Would you rather send a flirty meme or a bold pickup line?
49. What’s your favorite way for someone to flirt with you?
50. Would you rather win a staring contest with me or lose on purpose?
51. Would you rather I surprise you with a hug or a flirty wink?
52. What do you think is cuter—someone being shy or someone being bold?
53. Would you rather get a surprise kiss in the rain or under the stars?
54. What’s something completely random that makes you think someone likes you?
55. If I dared you to compliment me right now, what would you say?
56. Would you rather I challenge you to a flirty dare or truth?
57. Would you rather go for a midnight snack date or a sunrise breakfast date?
58. What’s something you secretly want to try on a date but haven’t yet?
59. If I sent you a flirty “thinking of you” text, how would you reply?
60. Would you rather take me out for a romantic dinner or cook for me at home?
61. What’s the silliest thing someone’s ever done to flirt with you?
62. Would you rather have a romantic snowball fight or a cozy blanket fort hangout?
63. If I dared you to make me laugh right now, what would you say?
64. Would you rather cuddle up during a scary movie or a cheesy romantic one?
65. Would you rather I send you a mystery note or a flirty doodle?
66. How do you feel about playful dares on a date?
67. Would you rather surprise someone or be surprised on a date?
68. Would you rather slow dance in the kitchen or under the moonlight?
69. What’s the boldest flirty text you’ve ever sent?
70. Would you rather hear a flirty compliment or a cheesy pickup line from me?
71. Would you rather hold hands during a movie or sneak a quick kiss?
72. Would you rather be the one who starts the flirting or the one who gets surprised by it?
73. If we had to play a flirty game together, what would you pick?

Final Thoughts

Flirty questions aren’t just about getting a guy’s attention—they’re about keeping the conversation playful, light, and full of chemistry. Whether you’re texting, hanging out, or looking for an icebreaker that’s a little more interesting than “Hey, how’s your day?”, these questions add a dash of fun and a whole lot of spark. Go ahead, ask away—and let the flirting games begin!