Would you rather questions

Pick who's playing and how bold to go. Every question has two answers worth defending.

Who are you with?
What mood?
How many?

  1. Read one out.
  2. Everyone picks a side.
  3. The fun is in the why, so ask it.

Want them spicier? Spicy would you rather questions

All 99 would you rather questions

Light

  1. Would you rather never use your phone at dinner again or never order dessert again?
  2. Would you rather be able to talk to animals or speak every human language?
  3. Would you rather give a toast at every wedding you go to or never be invited to one?
  4. Would you rather have a rewind button or a pause button for your life?
  5. Would you rather always be 10 minutes early or always 20 minutes late?
  6. Would you rather have a personal chef or a personal assistant?
  7. Would you rather give up cheese or chocolate forever?
  8. Would you rather sneeze glitter or hiccup bubbles?
  9. Would you rather have a theme song every time you walk into a room or a laugh track for everything you say?
  10. Would you rather be the funniest person in the room or the smartest?
  11. Would you rather give up music or give up movies and TV?
  12. Would you rather explore the deep ocean or outer space?
  13. Would you rather have your dream job with a two-hour commute or an okay job five minutes from home?
  14. Would you rather never wait in line again or never sit in traffic again?
  15. Would you rather have perfect weather on every day off or the best table at any restaurant?
  16. Would you rather be able to fly but only a foot off the ground, or turn invisible but only when nobody is looking?
  17. Would you rather speak only in rhymes for a day or sing everything you say?
  18. Would you rather have a dog that can talk or a cat that does your chores?
  19. Would you rather eat your favorite meal every day for a year or never eat it again?
  20. Would you rather be an extra in a famous movie or the star of a terrible one?
  21. Would you rather spend a year traveling with no plan or a year at home with no obligations?
  22. Would you rather never do laundry again or never wash another dish?
  23. Would you rather have free flights for life or free groceries for life?
  24. Would you rather play any instrument by ear or draw anything from memory?
  25. Would you rather have a house in the countryside or an apartment in the middle of the city?
  26. Would you rather spend a day in 1926 or a day in 2126?
  27. Would you rather only be able to whisper or only be able to shout?
  28. Would you rather host dinner for 12 every week or never host again?
  29. Would you rather know how every movie ends before you watch it or never be able to finish one?
  30. Would you rather always lose your keys or always forget why you walked into a room?
  31. Would you rather live in a treehouse or on a houseboat?
  32. Would you rather be great at small talk or great at public speaking?
  33. Would you rather have the world's best coffee every morning or the world's best bed every night?
  34. Would you rather win an Olympic medal or an Oscar?
  35. Would you rather always have wet socks or always have a pebble in your shoe?
  36. Would you rather have your life narrated by a sports commentator or a nature documentary host?
  37. Would you rather have a fridge that restocks itself or a suitcase that packs itself?
  38. Would you rather have a slide in your home or a secret room?
  39. Would you rather work from a beach with bad Wi-Fi or an office with a perfect view?
  40. Would you rather have every meeting turned into an email or every email turned into a meeting?
  41. Would you rather give a presentation in your pajamas or without any slides?
  42. Would you rather sit next to a coworker who talks nonstop or one who never replies?
  43. Would you rather have a desk by the window or a desk by the snacks?
  44. Would you rather run a team of 10 or work alone on something you love?
  45. Would you rather only have meetings before 9:00 am or only after 5:00 pm?
  46. Would you rather have dinner with your favorite author or your favorite musician?
  47. Would you rather be the friend who plans every get-together or the one who says yes to all of them?
  48. Would you rather have a first date at a fancy restaurant or a street food market?
  49. Would you rather have a partner who's a great cook or a great dancer?
  50. Would you rather plan every date for the rest of your life or never plan one again?
  51. Would you rather sleep on a couch for a month or go without hot showers for a month?
  52. Would you rather have to hop everywhere or skip everywhere?

Deep

  1. Would you rather have dinner with your 10-year-old self or your 80-year-old self?
  2. Would you rather live in a city you love with no friends there, or a city you dislike with all your friends?
  3. Would you rather have a perfect memory or be able to forget anything you choose?
  4. Would you rather always say exactly what you're thinking or never be able to speak your mind?
  5. Would you rather be the best player on a losing team or the worst player on a winning team?
  6. Would you rather be remembered for your kindness or your achievements?
  7. Would you rather have a few close friends or lots of good acquaintances?
  8. Would you rather relive your best day once more or never have a bad day again?
  9. Would you rather have one huge adventure a year or a small one every week?
  10. Would you rather know what everyone thinks of you or never know what anyone thinks of you?
  11. Would you rather redo one decision from your past or get a glimpse of your life in 10 years?
  12. Would you rather live one life that lasts 200 years or five lives of 40 years each?
  13. Would you rather have a job you love that pays little or a job you don't mind that pays a lot?
  14. Would you rather always be honest even when it hurts or always be kind even when it means bending the truth?
  15. Would you rather spend a year somewhere new where nobody knows you or a year back where you grew up?
  16. Would you rather have the courage to try anything or the patience to finish everything?
  17. Would you rather be a great listener or a great storyteller?
  18. Would you rather master one skill completely or be pretty good at 20 different things?
  19. Would you rather be known at work for your ideas or for how you treat people?
  20. Would you rather have a mentor who's brutally honest or one who's endlessly encouraging?
  21. Would you rather do work that's always interesting or work that's always calm?
  22. Would you rather have your family live next door or a flight away?
  23. Would you rather keep every photo you've ever taken or every message you've ever received?
  24. Would you rather have a quiet life with no surprises or a messy life full of stories?
  25. Would you rather know all the answers or always have good questions?

Bold

A little daring, never explicit

  1. Would you rather always know when someone is lying or always get away with lying?
  2. Would you rather be stuck in an elevator with your boss or your ex?
  3. Would you rather have your search history read out at a family dinner or your group chat read out at work?
  4. Would you rather be set up on a blind date by your best friend or by your family?
  5. Would you rather kiss in the rain or slow dance in the kitchen?
  6. Would you rather share a toothbrush or a phone with your partner for a month?
  7. Would you rather say "I love you" first or hear it first?
  8. Would you rather be caught singing alone in the car or rehearsing an argument out loud in the shower?
  9. Would you rather have your family sit in on your next work meeting or your coworkers sit in on your next family dinner?
  10. Would you rather accidentally reply-all to the whole company or send your manager a voice note meant for a friend?
  11. Would you rather perform a song you wrote at an open mic or read your teenage poetry out loud?
  12. Would you rather give an honest review of every gift you've ever received or confess every white lie you told last year?
  13. Would you rather let your best friend choose your next tattoo or your next partner?
  14. Would you rather do karaoke in front of your whole office or stand-up comedy in front of strangers?
  15. Would you rather let a friend read your texts for an hour or pick your outfits for a week?
  16. Would you rather have your most embarrassing moment become a meme or your proudest moment be forgotten?
  17. Would you rather go skydiving or swim with sharks?
  18. Would you rather eat a bug or sing on live TV?
  19. Would you rather tell everyone here your most embarrassing nickname or your worst habit?
  20. Would you rather spend a night alone in a haunted house or a week without talking to anyone?
  21. Would you rather say yes to every invitation for a month or no to every invitation for a month?
  22. Would you rather ask someone out in front of a crowd or be asked out in front of a crowd?

Questions about the questions

How do you play would you rather?

One person reads a question with two options. Everyone picks one and explains why, and any answer counts if you can defend it.

What makes a good would you rather question?

Two options that are both tempting or both a little awful, so nobody can answer in a second.

Try them on new people

Every week Timeleft seats small groups of strangers for dinner, coffee or a walk, with conversation prompts built in.