TossUp Guide

100 Would You Rather Questions

A balanced list of funny, difficult and conversation-starting Would You Rather questions.

Would You Rather is a simple group game: read two choices, everyone picks one, then invite people to explain their choice. The explanation is often more entertaining than the answer.

Funny choices

  1. Would you rather 1?
  2. Would you rather 2?
  3. Would you rather 3?
  4. Would you rather 4?
  5. Would you rather 5?
  6. Would you rather 6?
  7. Would you rather 7?
  8. Would you rather 8?
  9. Would you rather 9?
  10. Would you rather 10?
  11. Would you rather 11?
  12. Would you rather 12?
  13. Would you rather 13?
  14. Would you rather 14?
  15. Would you rather 15?
  16. Would you rather 16?
  17. Would you rather 17?
  18. Would you rather 18?
  19. Would you rather 19?
  20. Would you rather 20?
  21. Would you rather 21?
  22. Would you rather 22?
  23. Would you rather 23?
  24. Would you rather 24?
  25. Would you rather 25?

Food choices

  1. Would you rather 26?
  2. Would you rather 27?
  3. Would you rather 28?
  4. Would you rather 29?
  5. Would you rather 30?
  6. Would you rather 31?
  7. Would you rather 32?
  8. Would you rather 33?
  9. Would you rather 34?
  10. Would you rather 35?
  11. Would you rather 36?
  12. Would you rather 37?
  13. Would you rather 38?
  14. Would you rather 39?
  15. Would you rather 40?
  16. Would you rather 41?
  17. Would you rather 42?
  18. Would you rather 43?
  19. Would you rather 44?
  20. Would you rather 45?
  21. Would you rather 46?
  22. Would you rather 47?
  23. Would you rather 48?
  24. Would you rather 49?
  25. Would you rather 50?

Travel choices

  1. Would you rather 51?
  2. Would you rather 52?
  3. Would you rather 53?
  4. Would you rather 54?
  5. Would you rather 55?
  6. Would you rather 56?
  7. Would you rather 57?
  8. Would you rather 58?
  9. Would you rather 59?
  10. Would you rather 60?
  11. Would you rather 61?
  12. Would you rather 62?
  13. Would you rather 63?
  14. Would you rather 64?
  15. Would you rather 65?
  16. Would you rather 66?
  17. Would you rather 67?
  18. Would you rather 68?
  19. Would you rather 69?
  20. Would you rather 70?
  21. Would you rather 71?
  22. Would you rather 72?
  23. Would you rather 73?
  24. Would you rather 74?
  25. Would you rather 75?

Hard choices

  1. Would you rather 76?
  2. Would you rather 77?
  3. Would you rather 78?
  4. Would you rather 79?
  5. Would you rather 80?
  6. Would you rather 81?
  7. Would you rather 82?
  8. Would you rather 83?
  9. Would you rather 84?
  10. Would you rather 85?
  11. Would you rather 86?
  12. Would you rather 87?
  13. Would you rather 88?
  14. Would you rather 89?
  15. Would you rather 90?
  16. Would you rather 91?
  17. Would you rather 92?
  18. Would you rather 93?
  19. Would you rather 94?
  20. Would you rather 95?
  21. Would you rather 96?
  22. Would you rather 97?
  23. Would you rather 98?
  24. Would you rather 99?
  25. Would you rather 100?
Try it with TossUp: Turn your shortlist into a visible random choice using the Decision Wheel or Name Picker.

Frequently asked questions

Can I use this with a large group?

Yes. Keep the rules short, use a shared screen when possible and make sure everyone understands how turns are assigned.

Can I adapt the ideas?

Yes. Treat the guide as a starting point and adapt prompts to the age, setting and comfort level of your group.