Hard would you rather questions

40 questions. Genuinely tough but harmless dilemmas, for when the easy ones get too easy.

  1. Would you rather lose all music forever or lose all movies and TV shows forever?
  2. Would you rather always be ten minutes late or always be an hour early?
  3. Would you rather have every movie spoiled before you see it or have every book end one chapter early?
  4. Would you rather give up your favorite food forever or your favorite hobby forever?
  5. Would you rather live without air conditioning or without heating?
  6. Would you rather answer every question with total honesty or never be allowed to ask a question again?
  7. Would you rather have a job you love that nobody has heard of or a famous job you only sort of like?
  8. Would you rather be able to speak every language or play every musical instrument?
  9. Would you rather wear the same outfit every day or never wear the same outfit twice?
  10. Would you rather know all the answers but be unable to explain them or explain things beautifully but sometimes be wrong?
  11. Would you rather lose all your photos or all your saved messages?
  12. Would you rather be stuck on a long flight with no entertainment or stuck in traffic with one song on repeat?
  13. Would you rather always be slightly too hot or always be slightly too cold?
  14. Would you rather skip your favorite season for a year or skip your birthday celebration for a year?
  15. Would you rather never have to sleep or never have to eat?
  16. Would you rather choose every meal you eat but always eat alone or always eat with friends but never choose?
  17. Would you rather live in a tiny apartment in your dream city or a huge house somewhere you find dull?
  18. Would you rather never use a keyboard again or never use a touchscreen again?
  19. Would you rather be the best player on a losing team or the worst player on a winning team?
  20. Would you rather always know what time it is without a clock or always know which way is north?
  21. Would you rather redo one day of your choice every month or skip one day of your choice every month?
  22. Would you rather do all your chores in one long day each week or a little bit every single day?
  23. Would you rather read every terms and conditions page in full or listen to an hour of hold music every week?
  24. Would you rather give up your car or your phone for a year?
  25. Would you rather always hit every red light or always pick the slowest checkout line?
  26. Would you rather have a phone with endless battery but a cracked screen or a perfect screen that dies by lunch?
  27. Would you rather listen to one album for the rest of your life or never hear the same song twice?
  28. Would you rather give up all streaming services or all video games?
  29. Would you rather always remember people's names or always remember where you put things?
  30. Would you rather sit on the floor at every meal or sleep without a pillow for a year?
  31. Would you rather be great at starting conversations or great at ending them gracefully?
  32. Would you rather get every gift you ask for but never be surprised or always be surprised but sometimes miss the mark?
  33. Would you rather have a home with a beautiful garden but no view or an amazing view but no outdoor space?
  34. Would you rather choose your own name all over again or let your best friend pick your nickname forever?
  35. Would you rather win every board game you play or always pick the perfect movie for movie night?
  36. Would you rather be a famous artist whose work is misunderstood or an unknown artist whose work your friends love?
  37. Would you rather have unlimited free books or unlimited free movie tickets for life?
  38. Would you rather be an amazing singer with stage fright or an average singer who loves performing?
  39. Would you rather always think of the perfect reply five minutes too late or a so-so reply right away?
  40. Would you rather be the first person to try every new invention or wait until all the bugs are fixed?

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