Hard Would You Rather Questions

Most would you rather questions have an obvious winner. These don't. This set collects 87 hard would you rather questions where both sides cost you something real: knowing the future or changing the past, being famous or being truly happy, living a hundred years or reliving your best year forever. They're clean and thoughtful, and they're built to make you stop, frown, and actually think before you tap.

Hard questions are great for smaller groups who like a good debate, like a dinner table, a philosophy club, or a late-night road trip. They also make surprisingly good journal or discussion prompts for older students. After you choose, check the vote split. The best questions in this set land close to fifty-fifty, which tells you it really was a tough call for everyone.

How to play

1. Read the question and take a full ten seconds before answering.
2. Pick the side you'd live with, not the one that sounds cooler.
3. Talk through what you'd be giving up with your choice.
4. See the vote split and find out how divided other players were.

All 87 Hard Would You Rather Questions

1. Would you rather be the richest in a poor town or be the poorest in a rich town?
2. Would you rather have everyone like you or have everyone be honest with you?
3. Would you rather know how your love story ends or be surprised every step of the way?
4. Would you rather be the hero nobody knows about or be the celebrated hero who got lucky?
5. Would you rather forget your favorite memory or forget your most embarrassing memory?
6. Would you rather never have to sleep or never have to eat?
7. Would you rather choose your own dreams every night or never have a bad dream again?
8. Would you rather spend a month in the wilderness alone or spend a month in a big city alone?
9. Would you rather be friends with everyone or have three truly loyal friends?
10. Would you rather never lose anything again or never forget anything again?
11. Would you rather know the truth about everything or be blissfully unaware?
12. Would you rather know everything your partner is thinking or have your partner know everything you're thinking?
13. Would you rather know your future partner's name or know your future job?
14. Would you rather have a partner who loves your family or have a family who loves your partner?
15. Would you rather know every language or play every instrument?
16. Would you rather be able to fix any broken thing or be able to heal any broken heart?
17. Would you rather get into your dream college with no scholarship or get a full ride to your second choice?
18. Would you rather switch jobs every two years or stay at one company for 30 years?
19. Would you rather have your partner be your best friend or have your partner be your biggest cheerleader?
20. Would you rather be able to erase one mistake or be able to repeat one perfect moment?
21. Would you rather have unlimited PTO but a busy team or have three weeks off with coverage guaranteed?
22. Would you rather have the answer to any question once a year or have a hint to any question once a day?
23. Would you rather have a job that changes the world with no credit or have a job that gets you credit but changes little?
24. Would you rather know every recipe your grandparents made or know every story your grandparents lived?
25. Would you rather be loved but never respected or be respected but never loved?
26. Would you rather be the smartest person alive or be the happiest person alive?
27. Would you rather give up your phone forever or give up your car forever?
28. Would you rather find true love or find your true calling?
29. Would you rather be 30 forever or be wise like an 80-year-old but look your age?
30. Would you rather spend a year alone on a comfortable island or spend a year never having a minute alone?
31. Would you rather work for a startup with big risk or work for a big company with steady pay?
32. Would you rather have a photographic memory or have perfect intuition?
33. Would you rather have a job with a great team and okay pay or have a job with great pay and an okay team?
34. Would you rather lose all your memories or never be able to make new ones?
35. Would you rather have a best friend who always tells the truth or have a best friend who always has your back?
36. Would you rather have a perfect GPA or have a perfect social life?
37. Would you rather be able to talk to animals or be able to understand babies?
38. Would you rather lose every argument or never be allowed to argue?
39. Would you rather know all the answers but can't share them or share all you know but no one believes you?
40. Would you rather live without the internet or live without air travel?
41. Would you rather know the exact date of your happiest day or know the exact date of your hardest day?
42. Would you rather live in a world without color or live in a world without music?
43. Would you rather move every three years or stay in one town your whole life?
44. Would you rather be famous and forgotten after you die or be unknown now and remembered forever?
45. Would you rather never feel physical pain or never feel embarrassed?
46. Would you rather live near family or live near your best friends?
47. Would you rather be able to go back in time or be able to see the future?
48. Would you rather have perfect health but no friends or have many friends but always feel tired?
49. Would you rather be the new kid every year or never meet anyone new at school?
50. Would you rather take a sabbatical for six months or get a 20 percent raise?
51. Would you rather never be able to lie or never be able to hear a lie?
52. Would you rather know every answer on the SAT or know exactly what career will make you happy?
53. Would you rather relive your best day forever or live every day as a brand-new unknown?
54. Would you rather start life over at 18 with your current wisdom or stay exactly where you are now?
55. Would you rather always tell the truth or always be believed?
56. Would you rather have homework that is fun or have no homework at all but boring classes?
57. Would you rather give up music forever or give up movies and shows forever?
58. Would you rather always be 10 minutes late or always be 20 minutes early?
59. Would you rather save one close friend or save ten strangers?
60. Would you rather have one wish granted today or have three wishes granted in 20 years?
61. Would you rather have a rewind button for your life or have a pause button for your life?
62. Would you rather retire at 45 with a modest budget or retire at 65 with plenty to spare?
63. Would you rather lose your sense of taste or lose your sense of smell?
64. Would you rather have one close friend for 50 years or have 50 good friends you see a few times a year?
65. Would you rather always know the right thing to say or always know the right thing to do?
66. Would you rather live on a quiet farm with no neighbors or live in an apartment with the best neighbors?
67. Would you rather see the world as it was 500 years ago or see it as it will be 500 years from now?
68. Would you rather know the ending of every movie or never know how any movie ends?
69. Would you rather have the ability to stop aging or have the ability to heal others?
70. Would you rather be the best at one thing or be good at everything?
71. Would you rather be the boss of a job you hate or be the intern at a job you love?
72. Would you rather live 200 years in good health or live 80 years knowing every day will be happy?
73. Would you rather be stuck in the past with no tech or be stuck in the future with no family?
74. Would you rather be a genius nobody listens to or be average but always heard?
75. Would you rather be long-distance for a year or live together in a tiny studio for a year?
76. Would you rather be an expert on everything but never promoted or be promoted fast but always learning on the fly?
77. Would you rather have more time or have more money?
78. Would you rather make one decision perfectly each day or never regret any decision you make?
79. Would you rather travel the world alone or stay home with the people you love?
80. Would you rather be a great leader or be a great friend?
81. Would you rather never feel fear or never feel sadness?
82. Would you rather apologize to everyone you ever wronged or hear an apology from everyone who wronged you?
83. Would you rather have a job you love that pays okay or have a job you tolerate that pays great?
84. Would you rather spend a day as your own kid or spend a day as your own parent?
85. Would you rather be a kid forever or be a grown-up right now?
86. Would you rather read everyone's mind all the time or have everyone read yours once a day?
87. Would you rather always know what your boss thinks of you or never worry about what your boss thinks of you?

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