50 Valentine’s Day Would You Rather Questions: Creating Magical Moments [Free Printable Checklist]

Valentine's Day Would You Rather Questions free PDF


Valentine’s Day is just around the corner, and it’s the perfect time to plan a celebration filled with love and romance. In this post, we’re excited to bring you 50 enchanting “Valentine’s Day Would You Rather” questions that will add a touch of magic to your celebration.

Additionally, we’ll be embedding a video featuring these questions, and for your convenience, we’re offering a free printable checklist to make planning even easier. Let’s dive into the world of choices and make this Valentine’s Day truly special!

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Valentine’s Day Would You Rather Questions

1. Flowers or Chocolates:
Kick off your celebration with a classic dilemma – a bouquet of fresh flowers or a box of decadent chocolates?

2. Romantic Dinner or Home-cooked Meal:
Set the tone for the evening: a romantic dinner at a fancy restaurant or the intimacy of a home-cooked meal? Check out The Date Night Cookbook for romantic dinner recipes and ideas.

3. Handwritten Love Letter or Digital Message:
Explore the charm of a handwritten love letter or the convenience of a heartfelt digital message.

4. Red Roses or Mixed Bouquet:
Express your feelings with classic red roses or opt for a burst of colors and variety with a mixed bouquet.

5. Candlelit Dinner or Movie Night In:
Create a cozy atmosphere with a candlelit dinner or enjoy a relaxed movie night at home. Scented candles can contribute to creating a more soothing and enchanting ambiance, making them a unique and intriguing Valentine’s Day present.

6. Sunset Walk or Starry Night Stroll: Would you prefer a romantic stroll during the colorful hues of a sunset or the magical ambiance of a starry night?

7. Spa Day or Adventure Date: Indulge in relaxation with a spa day or ignite excitement with an adventurous outing? A gift card for a spa and wellness experience is an ideal choice for a Valentine’s Day present as well.

8. Breakfast in Bed or Fancy Brunch: Start your day with cozy intimacy by having breakfast in bed or indulge in a luxurious brunch experience?

9. Love Songs Playlist or Romantic Movie: Set the mood with a curated love songs playlist or immerse yourselves in the magic of a romantic movie night.

10. Poetry Reading or Love Song Singing: Celebrate the arts by either reading romantic poetry together or singing your favorite love songs.

Valentine's Day Would You Rather Questions free PDF

Valentine’s Day This or That Questions

11. Heart-shaped Pizza or Classic Margherita: Add a playful touch with heart-shaped pizza or savor the timeless flavors of a classic Margherita. Get a heart-shaped pizza pan if you’re into making it yourself.

12. Homemade Dessert or Store-bought Treat: Show your culinary skills by preparing a homemade dessert or opt for a delightful store-bought treat. Need ideas for what to bake, check out Claire Saffitz’s Simple Recipes for Dessert People.

13. Hot Air Balloon Ride or Beach Picnic: Soar to new heights with a hot air balloon ride or enjoy a cozy beach picnic.

14. Dancing Under the Stars or Slow Dance: Create magical moments by dancing under the stars or cherish the intimacy of a slow dance at home.

15. Surprise Gift or Planned Activity: Surprise your partner with a thoughtful gift or plan a memorable activity for your celebration.

16. Wine Tasting or Craft Beer Sampling: Explore your palate with an elegant wine tasting or discover unique flavors with a craft beer sampling.

17. Morning Cuddles or Evening Snuggles: Choose between the coziness of morning cuddles or the warmth of evening snuggles. Enjoy your sweet and comfortable time in matching pajamas for couples.

18. Hand-in-hand Walk or Linked Arms: Enhance your connection with a hand-in-hand walk or opt for the sweet simplicity of linked arms.

19. Vintage Love Letters or Modern Texts: Dive into the romantic past with vintage love letters or stay connected in the present with modern texts.

20. DIY Craft Night or Art Gallery Visit: Unleash your creativity with a DIY craft night or appreciate the works of others at an art gallery.

Would You Rather: Valentine’s Day Edition

21. Heart-shaped Pancakes or Waffles: Start the day with a loving touch – heart-shaped pancakes or the delightful crunch of waffles.

22. Polaroid Pictures or Professional Photos: Capture the moment with the charm of Polaroid pictures or invest in professional photography.

23. Romantic Getaway or Cozy Staycation: Embark on a romantic getaway or create a cozy staycation experience at home.

24. Comedy Show or Romantic Play: Laugh together at a comedy show or immerse yourselves in the romance of a theater play.

25. Stargazing or City Skyline View: Marvel at the beauty of the night sky with stargazing or enjoy the urban charm of a city skyline view.

26. Matching Outfits or Complementary Colors: Show your unity with matching outfits or opt for a coordinated look with complementary colors.

27. Cooking Together or Ordering In: Bond in the kitchen by cooking together or savor the simplicity of ordering in.

28. Ferris Wheel Ride or Carousel Spin: Experience the thrill of a Ferris wheel ride or enjoy the whimsy of a carousel spin.

29. Love Poem or Love Song Dedication: Express your feelings through the written word with a love poem or dedicate a special song.

30. Board Game Night or Puzzle Challenge: Fuel friendly competition with a board game night or embrace collaboration with a puzzle challenge. These 3D puzzles make for fantastic and distinctive Valentine’s Day presents, fostering delightful bonding moments.

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Valentine's Day Would You Rather quiz
Valentine's Day This or That Questions

Valentine’s Day Would You Rather Quiz

31. Chocolate-covered Strawberries or Fondue: Indulge in sweet delights with chocolate-covered strawberries or elevate the experience with fondue.

32. Salsa Dancing or Ballroom Dancing: Spice up the night with energetic salsa dancing or embrace elegance with ballroom dancing.

33. Breakfast in Pajamas or Brunch in Fancy Attire: Choose between a laid-back morning with breakfast in pajamas or a stylish brunch in fancy attire.

34. Arcade Games or Mini Golf: Enjoy a playful date with arcade games or test your precision with a round of mini-golf.

35. Beach Sunset or Mountain Sunrise: Witness the beauty of nature with a romantic beach sunset or a serene mountain sunrise.

36. Sweet or Savory Valentine’s Treats: Indulge your taste buds with a choice between sweet or savory Valentine’s treats.

37. Memory Lane Walk or Future Plans Talk: Take a stroll down memory lane or engage in a heartfelt conversation about future plans.

38. Roller Skating or Ice Skating: Experience the joy of movement with roller skating or the icy charm of ice skating.

39. Love Notes Hidden or Love Notes Openly: Express your affection by either hiding love notes for your partner to find or openly sharing your sentiments.

40. Horseback Riding or Bike Riding: Enjoy the outdoors with a romantic horseback ride or a leisurely bike ride together.

Delightful Choices for Valentine’s Day

41. Chocolate Fondue or Cheese Fondue: Indulge in the richness of chocolate fondue or savor the savory delight of cheese fondue.

42. Sunrise Hike or Sunset Cruise: Connect with nature by choosing between a refreshing sunrise hike or a serene sunset cruise.

43. Breakfast in Bed or Breakfast at a Café: Begin the day with intimacy by having breakfast in bed or embrace the charm of a café.

44. Wine and Cheese Night or Beer and Pretzels: Create a delightful evening with wine and cheese or go for a casual vibe with beer and pretzels.

45. Poetry Writing Together or Reading Aloud: Share creative moments by writing poetry together or enjoy the beauty of spoken words by reading aloud.

46. Picnic in the Park or Picnic on the Beach: Choose between the lush greenery of a picnic in the park or the soothing sounds of a beach picnic.

47. Movie Marathon at Home or Theater Date: Curate your cinematic experience with a cozy movie marathon at home or elevate it with a date night at the theater.

48. Art Museum Visit or Sculpture Garden Stroll: Immerse yourselves in culture with an art museum visit or appreciate the outdoors with a sculpture garden stroll.

49. Couples Massage or DIY Massage: Relax and unwind with a luxurious couples massage or opt for a more personal touch with a DIY massage at home.

50. Starlit Campfire or Fireplace Snuggle: End your day with a touch of warmth – a starlit campfire or a cozy fireplace snuggle.

Valentine’s Day Would You Rather Quiz Video

Grab your partner, or friends, or treat yourself to a solo celebration, and join us on exploring this journey of love and ultimate Valentine’s Day choices.

Free Printable Checklist

Valentine's Day This or That questions free PDF

We’re offering a free printable checklist of all 50 “Valentine’s Day This or That” questions to make your planning easier. Download and print it to guide you through a romantic and memorable celebration.


These 50 Valentine’s Day Would You Rahter questions are designed to inspire romantic moments and help you create lasting memories on this special day. Feel free to mix and match, and don’t forget to check out the video featuring these questions.

Whether you’re in a relationship, celebrating with friends, or enjoying some self-love, these choices are sure to make your Valentine’s Day special. Share your favorite picks in the comments, and may your celebration be filled with love, joy, and enchanting moments! Happy Valentine’s Day!

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