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60+ Would You Rather Questions to Ask Your Boyfriend

Cute, funny and thoughtful questions to learn more about him.

These Would You Rather questions to ask your boyfriend are cute, funny and sometimes a little deep. Use them over text, on date night or on a long drive to find out how he really thinks, and maybe win a few debates.

How to play

Ask him a question and guess his answer before he replies. If you guess right, you pick the next date. Over text, send one question a day and keep the best answers. 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 Boyfriend Would You Rather Questions

1. Would you rather have me cook you dinner or have me plan a surprise day out?

Home-cooked love or a day full of surprises.

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2. Would you rather watch a game together or play a video game together?

Fan mode or player mode.

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3. Would you rather go on a hike with me or go to the movies with me?

Fresh air or popcorn.

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4. Would you rather have me surprise you at work with lunch or have me leave notes in your car?

Lunch delivery or windshield love notes.

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5. Would you rather have a weekend fishing trip together or have a weekend city trip together?

Quiet lake or busy streets.

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6. Would you rather get a handwritten letter from me or get a playlist made by me?

Words or songs.

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7. Would you rather learn to cook my favorite meal or have me learn to cook yours?

Who is the chef in this relationship?

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8. Would you rather have me wear your hoodie forever or have me steal the blanket every night?

Two classic girlfriend crimes.

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9. Would you rather go to a concert of my favorite band or go to a game of your favorite team?

Whose world are we stepping into?

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10. Would you rather spend a lazy Sunday in bed watching shows or spend Sunday trying a new activity?

Couch or adventure.

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11. Would you rather have a pet dog together or have a pet cat together?

Walks or purrs.

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12. Would you rather build furniture together or paint a room together?

Teamwork test either way.

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13. Would you rather have me cheer you on at every game or have me make your favorite snacks for every game?

Loudest fan or best snack chef.

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14. Would you rather take a road trip with only your playlist or take a road trip with only mine?

Who controls the music decides everything.

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15. Would you rather go camping in a tent or go "glamping" in a cabin?

Roughing it or comfy outdoors.

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16. Would you rather have me be better than you at video games or have me be better than you at sports?

Which loss would bug you more?

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17. Would you rather get matching jackets or get matching sneakers?

Couple style goals.

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18. Would you rather spend our anniversary at a fancy dinner or spend it at the place we first met?

Fancy or nostalgic.

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19. Would you rather have me know all your friends' names or have me get along great with your family?

Both matter. Which one first?

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20. Would you rather grill burgers together in the backyard or make homemade pizza together?

Backyard chef or pizza night.

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21. Would you rather win a game night against me or win a cooking contest against me?

Bragging rights in which arena?

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22. Would you rather get a surprise gift for no reason or get a big gift on your birthday?

Random love or planned love.

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23. Would you rather go to a car show with me or go to an art museum with me?

Engines or paintings.

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24. Would you rather plan our next vacation or let me plan it?

Leader or passenger.

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25. Would you rather have me text you good morning every day or have me call you every night?

Morning love or night love.

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26. Would you rather watch a horror movie with me or watch a rom-com with me?

Scared hugs or sappy smiles.

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27. Would you rather go to a theme park together or go to a water park together?

Roller coasters or water slides.

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28. Would you rather have a bromance with my brother or have my dad as your best friend?

Making my family your family.

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29. Would you rather teach me your favorite hobby or learn my favorite hobby?

Teacher or student.

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30. Would you rather go on a double date with your best friend or go on a double date with my best friend?

Whose friends are more fun?

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31. Would you rather have breakfast together every Saturday or have dinner out every Friday?

Weekend start or weekend kickoff.

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32. Would you rather always pick the movie or always pick the restaurant?

Which choice matters more to you?

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33. Would you rather be called a cute nickname in public or keep nicknames private?

Proud or private.

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34. Would you rather have me show up at your game with a sign or have me show up with snacks for the whole team?

Loud love or tasty love.

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35. Would you rather build a treehouse together or build a backyard fire pit together?

Childhood dream or cozy nights.

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36. Would you rather get a massage after a long day or get your favorite meal after a long day?

Relax or refuel.

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37. Would you rather go on a fishing trip or go on a snowboarding trip?

Patience or speed.

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38. Would you rather have me plan a surprise party for you or have a quiet birthday with just me?

Big crowd or just us.

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39. Would you rather dance at a wedding together or sing karaoke together?

Moves or mic.

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40. Would you rather watch the sunrise together or watch the stars together?

Early or late romance.

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41. Would you rather have our first trip be to the beach or have it be to the mountains?

Waves or peaks.

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42. Would you rather go go-karting or go bowling?

Speed or strikes.

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43. Would you rather have me wear your jersey or have me wear your favorite color?

Fan gear or your color.

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44. Would you rather have a secret handshake together or have a secret code word together?

Move or word.

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45. Would you rather take a dance class with me or take a cooking class with me?

Steps or recipes.

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46. Would you rather spend a day doing everything I like or spend a day doing everything you like?

Fair trade?

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47. Would you rather get a care package from me when you are sick or have me come over and take care of you?

Box of love or in-person love.

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48. Would you rather go to an escape room together or go to a trampoline park together?

Brains or bounce.

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49. Would you rather have me know your coffee order by heart or have me know your favorite song by heart?

Details that make you feel loved.

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50. Would you rather ride a tandem bike together or paddle a canoe together?

Teamwork on wheels or water.

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51. Would you rather have me laugh at all your jokes or have me tell you the truth when a joke is bad?

Fan or honest critic.

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52. Would you rather cook breakfast together or order brunch together?

Kitchen fun or restaurant fun.

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53. Would you rather get a photo album of our memories or get a video of our memories?

Pages or playback.

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54. Would you rather have a Netflix night every week or have a game night every week?

Watch or play.

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55. Would you rather go on a hot air balloon ride or go on a helicopter tour?

Slow and floaty or fast and loud.

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56. Would you rather have me surprise you with tickets or have me surprise you with a weekend away?

Event or escape.

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57. Would you rather go to a farmers market together or go to a flea market together?

Fresh food or treasures.

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58. Would you rather do a puzzle together or build a LEGO set together?

Pieces or bricks.

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59. Would you rather have our song be a slow song or have our song be a fast song?

Romantic or fun.

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60. Would you rather spend a holiday with my family or spend a holiday with yours?

Which table first?

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Frequently asked questions

How do you play boyfriend 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 boyfriend questions family friendly?

Yes. Every question on WouldYouRather.info is clean and safe for kids, classrooms, families and work events.

How many boyfriend questions are there?

This page has 60 boyfriend Would You Rather questions, and we add new ones regularly.

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