Date night Would You Rather questions turn small talk into real conversation. Some are playful, some are thoughtful, and all are clean, so they work on a first date, a dinner date or a cozy night in.
How to play
Take turns asking over dinner. After each answer, ask one follow-up question like “why?” or “has that ever happened to you?”. The best stories come from the follow-ups. Want to play online instead? Press the Play button above to vote on each question and see what percentage of players agreed with you.
60 Date Night Would You Rather Questions
1. Would you rather go to a fancy dinner or go to a food truck festival?
Candlelight or street food.
Vote and see results →2. Would you rather watch a romantic movie or watch a comedy movie?
Swoon or laugh.
Vote and see results →3. Would you rather cook dinner together at home or order takeout and build a blanket fort?
Chefs or cozy.
Vote and see results →4. Would you rather go stargazing or go to a rooftop cafe with city lights?
Real stars or city stars.
Vote and see results →5. Would you rather have a picnic date or have a museum date?
Sunshine or culture.
Vote and see results →7. Would you rather take a dance class together or take a cooking class together?
Moves or meals.
Vote and see results →9. Would you rather go on a sunset walk or go on a sunrise hike?
Evening glow or morning glow.
Vote and see results →10. Would you rather have a board game date or have a video game date?
Cards or controllers.
Vote and see results →11. Would you rather visit a bookstore and pick books for each other or visit a record store and pick songs for each other?
Stories or sounds.
Vote and see results →13. Would you rather have a themed date night at home or go out somewhere you have never been?
Creative or adventurous.
Vote and see results →14. Would you rather share one big dessert or order two different desserts and swap halfway?
Sharing is caring either way.
Vote and see results →15. Would you rather take a boat ride or take a hot air balloon ride?
Water or sky.
Vote and see results →16. Would you rather go to an art class and paint each other or go to a pottery class together?
Portraits or pots.
Vote and see results →17. Would you rather plan a surprise date or be surprised by a date?
Planner or guest.
Vote and see results →18. Would you rather have a karaoke date or have a trivia night date?
Sing or think.
Vote and see results →19. Would you rather go to a drive-in movie or go to a fancy cinema with recliners?
Classic or comfy.
Vote and see results →20. Would you rather go to a farmers market and cook what you buy or go to a fancy grocery store and pick a mystery dinner?
Fresh or fun.
Vote and see results →21. Would you rather ask each other 36 deep questions or play would you rather all night?
Deep or fun.
Vote and see results →22. Would you rather write each other a letter on date night or make each other a playlist?
Words or songs.
Vote and see results →24. Would you rather have a candlelit dinner at home or have a candlelit dinner in a restaurant?
Home or out.
Vote and see results →25. Would you rather do a puzzle together or build a LEGO set together?
Pieces or bricks.
Vote and see results →26. Would you rather go to a pumpkin patch or go to a flower farm?
Fall date or spring date.
Vote and see results →27. Would you rather have a spa night at home or have a movie marathon at home?
Relax or binge.
Vote and see results →28. Would you rather take a cooking challenge with a mystery ingredient or bake a cake from scratch together?
Chopped or bake-off.
Vote and see results →29. Would you rather take silly photos in a photo booth or take nice photos at a beautiful place?
Goofy or gorgeous.
Vote and see results →30. Would you rather go to a sports game or go to a play at the theater?
Cheers or applause.
Vote and see results →31. Would you rather go on a double date or go on a date just the two of you?
Group fun or one-on-one.
Vote and see results →32. Would you rather have a date at the beach or have a date in the mountains?
Sand or snow.
Vote and see results →34. Would you rather have dinner with no phones or have dinner where you text only in emojis?
Present or playful.
Vote and see results →35. Would you rather recreate your first date or plan a date you have never done before?
Nostalgia or newness.
Vote and see results →36. Would you rather have a breakfast date or have a late-night dessert date?
Early or late.
Vote and see results →37. Would you rather go to a cooking show taping or go to a TV game show taping?
Behind the scenes either way.
Vote and see results →38. Would you rather have a scavenger hunt date around town or have a mystery dinner date?
Explore or solve.
Vote and see results →39. Would you rather learn a magic trick for your date or learn a song on guitar for your date?
Wow or serenade.
Vote and see results →40. Would you rather try a new restaurant every date night or have one favorite restaurant forever?
Explorer or regular.
Vote and see results →41. Would you rather go on a bike ride date or go on a kayak date?
Pedal or paddle.
Vote and see results →42. Would you rather make homemade pizza together or make homemade sushi together?
Dough or rice.
Vote and see results →43. Would you rather spend date night volunteering or spend date night taking a class?
Give or grow.
Vote and see results →44. Would you rather go to a fair with games and rides or go to a fancy garden?
Fun or flowers.
Vote and see results →45. Would you rather dress up in your fanciest clothes or wear matching pajamas?
Gala or cozy.
Vote and see results →46. Would you rather have a dessert-only dinner date or have a breakfast-for-dinner date?
Sweet or brunchy.
Vote and see results →47. Would you rather go on a road trip for a day or have a staycation in a hotel?
Drive or stay.
Vote and see results →48. Would you rather watch the sunset from a hill or watch the city lights from a tall building?
Nature or skyline.
Vote and see results →49. Would you rather plan date nights by spinning a wheel or take turns planning every date?
Chance or turns.
Vote and see results →50. Would you rather have a date where you only speak in movie quotes or have a date where you only ask questions?
Funny or curious.
Vote and see results →51. Would you rather go to a jazz club or go to a live acoustic cafe?
Smooth or soft.
Vote and see results →52. Would you rather learn to make fancy coffee together or learn to make fancy milkshakes together?
Coffee art or milkshake art.
Vote and see results →53. Would you rather have date night at an arcade or have date night at a bowling alley?
Tickets or strikes.
Vote and see results →55. Would you rather take a cooking class from another country or take a dance class from another country?
Taste the world or dance the world.
Vote and see results →56. Would you rather have a stay-at-home movie night with homemade popcorn or go to the cinema with all the snacks?
Home or theater.
Vote and see results →57. Would you rather make a bucket list together or make a vision board together?
Plans or dreams.
Vote and see results →58. Would you rather have a date by the fireplace or have a date on a balcony?
Warm or breezy.
Vote and see results →59. Would you rather go to an escape room or go to an axe throwing place?
Puzzles or bullseyes.
Vote and see results →60. Would you rather have a date with no plan at all or have a date planned to the minute?
Wing it or schedule it.
Vote and see results →Frequently asked questions
How do you play date night Would You Rather?
Read a question out loud, everyone picks one of the two options, and each person explains why. No answering "both" or "neither". You can also tap a question here to vote online and see how other players chose.
Are these date night questions family friendly?
Yes. Every question on WouldYouRather.info is clean and safe for kids, classrooms, families and work events.
How many date night questions are there?
This page has 60 date night Would You Rather questions, and we add new ones regularly.