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Would You Rather?

20 dilemmas

Deep

Deep would you rather questions don't have funny answers — they have revealing ones. These 20 weigh time against money, kindness against achievement and a quiet life against an exciting one, which makes them good for road trips, first dates and late-night talks with old friends.

All the questions

  1. Relive your favorite day once a year or See one day of your future
  2. Do a job you love that pays little or Do a job you don't mind that pays a lot
  3. Be remembered for your kindness or Be remembered for your achievements
  4. Live in a big city or Live in a small village
  5. Have a few very close friends or Have many good friends
  6. Speak every language or Play every instrument
  7. Travel the world for a year or Have your dream home right now
  8. Always say exactly what you think or Never say anything you'd regret
  9. Change one past decision or See how it would have turned out, without changing it
  10. Be ten years older with everything you've learned or Be ten years younger and start again
  11. Have more time or Have more money
  12. Be the best in the world at one thing or Be good at many things
  13. Read minds or Have everyone always tell you the truth
  14. Have a quiet, peaceful life or Have an exciting, unpredictable life
  15. Learn something new every day or Teach someone something every day
  16. Meet your younger self or Meet your older self
  17. Never feel embarrassed again or Never feel bored again
  18. Lose all your photos or Lose all your messages
  19. Have a perfect memory or Be able to forget anything you choose
  20. Know what everyone thinks of you or Never know what anyone thinks of you
Shuffle this deck →
Try yours

Frequently asked questions

What makes a would you rather question deep?

Both options are reasonable choices people really make, so the answer shows what someone values — like a job you love that pays little or one you don't mind that pays a lot.

Are deep would you rather questions good for couples?

Yes, and for friends. They're gentle ways into bigger topics — family, work, regrets — without anyone feeling interviewed.

Is there a right answer?

No. The point is the reason behind each choice, and people often surprise themselves.