61 Playful Would You Rather Questions for Your Crush to Spark Flirting and Fun

Want to break the ice with your crush without sounding too obvious? “Would You Rather” questions are the perfect way to keep things light, playful, and just a little flirty. They’re a great excuse to get to know each other better while sneaking in some sweet (or cheeky) moments. Whether you’re texting late at night, sitting next to each other in class, or on a casual hangout, these would you rather questions for your crush can make the conversation fun, flirty, and unforgettable.

Why “Would You Rather” Questions Are the Perfect Way to Flirt with Your Crush

Flirting doesn’t always have to be serious or intense. Sometimes, the best way to build chemistry is by keeping things playful and teasing. “Would You Rather” questions let you casually flirt without putting too much pressure on the conversation. They create space for laughter, playful banter, and maybe even some blushing confessions—all while giving you a chance to learn more about what makes your crush tick.

61 Sweet, Silly, and Slightly Flirty Would You Rather Questions for Your Crush

1. Would you rather go on a cozy dinner date or an adventurous day trip?
2. Would you rather get a flirty text from me during the day or a goodnight message?
3. Would you rather be caught blushing or catch me blushing?
4. Would you rather slow dance under the stars or watch a movie under a blanket?
5. Would you rather get a surprise kiss or give one?
6. Would you rather share your favorite song or your biggest secret with me?
7. Would you rather flirt face to face or over text?
8. Would you rather have me make the first move or do it yourself?
9. Would you rather cuddle up watching a scary movie or a cheesy rom-com?
10. Would you rather accidentally call me “babe” in front of friends or have me do it?
11. Would you rather win a cute couple’s game or let me win on purpose?
12. Would you rather get a sweet handwritten note or a surprise snack from me?
13. Would you rather have a crush on someone who makes you laugh or someone who gives the best hugs?
14. Would you rather share a milkshake or a giant pizza with me?
15. Would you rather dance in the rain or cuddle by a fireplace?
16. Would you rather get stuck in an elevator with me or get lost on a hike?
17. Would you rather always have to call me by a cute nickname or let me pick one for you?
18. Would you rather go on a surprise road trip with me or a planned date night?
19. Would you rather tease me or be teased by me?
20. Would you rather have a flirty TikTok duet or a funny couple’s selfie go viral?
21. Would you rather kiss during a fireworks show or under the stars?
22. Would you rather see me in casual comfy clothes or all dressed up?
23. Would you rather play truth or dare or Would You Rather with me?
24. Would you rather steal my hoodie or let me steal yours?
25. Would you rather go for a late-night walk or an early morning coffee date?
26. Would you rather get caught staring at me or catch me staring at you?
27. Would you rather flirt through emojis or playful selfies?
28. Would you rather I send you a flirty meme or a sweet song?
29. Would you rather plan the perfect date or let me surprise you?
30. Would you rather get a flirty compliment from me or a teasing dare?
31. Would you rather have your hand held or your hair played with?
32. Would you rather I dare you to tell me a secret or ask you to share a memory?
33. Would you rather challenge me to a flirty staring contest or a tickle fight?
34. Would you rather write me a poem or draw me a doodle?
35. Would you rather have a cozy picnic or a sunset drive?
36. Would you rather have a crush on someone bold or someone shy?
37. Would you rather get a flirty wink across the room or a note passed under the table?
38. Would you rather share your favorite romantic song or your cheesiest love song?
39. Would you rather do a TikTok dance together or have a karaoke duet?
40. Would you rather get caught sneaking a flirty text or sneaking a smile at me?
41. Would you rather have an awkward first date story or a perfect one?
42. Would you rather hear me say “I like you” first or say it yourself?
43. Would you rather share an inside joke or a secret handshake?
44. Would you rather have me write your name in my notebook or draw a heart next to it?
45. Would you rather flirt during a group chat or in person?
46. Would you rather win a couple’s trivia game or have the best couple’s costume?
47. Would you rather get a playlist of songs that remind me of you or a list of reasons I like you?
48. Would you rather get lost together on purpose or accidentally?
49. Would you rather me call you cute in front of everyone or whisper it just to you?
50. Would you rather do a cheesy couple’s photoshoot or take random selfies?
51. Would you rather we share a secret spot to hang out or a secret handshake?
52. Would you rather flirt with me in person or over Snapchat?
53. Would you rather be stuck in a photo booth or on a Ferris wheel with me?
54. Would you rather have a sweet goodbye hug or a playful nudge?
55. Would you rather send me a flirty dare or accept one from me?
56. Would you rather have our friends ship us or not know at all?
57. Would you rather go on a double date or a secret solo date?
58. Would you rather spend a lazy Sunday cuddling or playing video games together?
59. Would you rather have your name as my phone wallpaper or your selfie?
60. Would you rather kiss in the rain or during a snowstorm?
61. Would you rather be my crush for a day or my date for a week?

Final Thoughts

These would you rather questions are a fun, low-pressure way to sprinkle a little flirtation into your conversations with your crush. They’re playful, sweet, and just cheeky enough to keep things exciting without going overboard. Pick a few, see where the conversation goes, and enjoy the giggles, blushing, and maybe even a little extra spark between you.