50 Valentine’s Day Would You Rather Questions to Add Fun, Laughter, and Love to Your Day

Valentine’s Day doesn’t have to be all roses, chocolates, and candlelit dinners. Sometimes, the best way to celebrate love (or just have a laugh at love’s expense) is with a playful game of “Would You Rather.” These Valentine’s Day-themed questions are sweet, silly, and just the right amount of spicy—perfect for couples, friends, or anyone who wants to add some fun and connection to the day of love.

Why Valentine’s Day Would You Rather Questions Are the Perfect Icebreaker

Whether you’re on a first date, hanging with your galentines, or cozying up with your long-term love, these questions help you break the ice, share laughs, and maybe even discover something new about each other. They spark playful debates, giggles, and “Wait, you’d really pick that?!” moments that make Valentine’s Day a little more memorable and a lot more fun.

50 Fun, Flirty, and Sweet Valentine’s Day Would You Rather Questions

1. Would you rather receive a handmade card or a fancy store-bought one?
2. Would you rather get chocolate or flowers on Valentine’s Day?
3. Would you rather go on a romantic dinner date or have a cozy movie night at home?
4. Would you rather receive a surprise date night or plan the perfect one yourself?
5. Would you rather have a Valentine’s Day picnic at the beach or in a cozy cabin?
6. Would you rather get 100 tiny Valentine’s cards or one giant one?
7. Would you rather get a serenade in public or a private love song at home?
8. Would you rather write a love poem or receive one?
9. Would you rather get candy hearts or heart-shaped pizza?
10. Would you rather have a Valentine’s Day themed karaoke night or dance party?
11. Would you rather wear all red or all pink on Valentine’s Day?
12. Would you rather watch a romantic comedy or an action movie on Valentine’s Day?
13. Would you rather have dinner by candlelight or fairy lights?
14. Would you rather celebrate with a big group or just your special someone?
15. Would you rather get a giant teddy bear or a box of mystery chocolates?
16. Would you rather cook dinner together or order in your favorite takeout?
17. Would you rather have a Valentine’s Day scavenger hunt or a cozy at-home spa night?
18. Would you rather make Valentine’s Day cookies or cupcakes?
19. Would you rather give out Valentine’s to your entire class or just your crush?
20. Would you rather have a heart-shaped pizza or heart-shaped pancakes?
21. Would you rather get a gift you hinted at or a total surprise?
22. Would you rather cuddle up in blankets or go on an adventurous date?
23. Would you rather spend Valentine’s Day in Paris or New York City?
24. Would you rather write love notes for each other or make a playlist of love songs?
25. Would you rather make chocolate fondue or have strawberry shortcake?
26. Would you rather have an awkward Valentine’s blind date or no date at all?
27. Would you rather give or receive homemade gifts?
28. Would you rather get a cute stuffed animal or a handwritten love letter?
29. Would you rather have a Valentine’s brunch or midnight dessert date?
30. Would you rather get caught kissing under mistletoe (in February!) or be serenaded by friends?
31. Would you rather get a bouquet of roses or a bouquet of your favorite snacks?
32. Would you rather spend the day baking together or crafting Valentine’s gifts?
33. Would you rather do a couple’s TikTok dance challenge or a funny love-themed prank?
34. Would you rather have matching Valentine’s Day pajamas or T-shirts?
35. Would you rather go ice skating hand-in-hand or ride bikes together?
36. Would you rather have a surprise love letter mailed to you or hidden in your backpack?
37. Would you rather win a Valentine’s Day couple’s trivia or a karaoke battle?
38. Would you rather have dinner on a rooftop or by the fireplace?
39. Would you rather get a candy heart with your crush’s name or have them like your post?
40. Would you rather create a Valentine’s TikTok together or make a scrapbook?
41. Would you rather get a chocolate fountain or a popcorn machine for your date night?
42. Would you rather spend Valentine’s Day in pajamas all day or get all dressed up?
43. Would you rather spend the day writing love poems or decorating cupcakes?
44. Would you rather have a Valentine’s game night or a movie marathon?
45. Would you rather send a flirty Valentine’s text or a cute video message?
46. Would you rather get serenaded by your crush or your best friend?
47. Would you rather plan a dream vacation with your Valentine or an epic local adventure?
48. Would you rather get a mystery box of love letters or a jar of sweet compliments?
49. Would you rather host a Valentine’s party or have a chill night for two?
50. Would you rather send anonymous Valentine’s cards to your crush or your best friends?

Final Thoughts

Valentine’s Day is the perfect excuse to play, flirt, laugh, and connect—whether you’re single, taken, or somewhere in between. These Valentine’s Day “Would You Rather” questions are an easy, light-hearted way to sprinkle some extra fun into your celebrations, your group chats, or your cozy nights in. Because love should always come with a side of giggles.