Would You Rather is a game that can be played with anyone, but if you want to get to know your friends or team on a deeper level, try out these Deep Would You Rather Questions. Answering these questions will force you to think a little deeper about your values and beliefs. Great way to get to know other people on a more serious level.

If you are in the mood for something a little bit more light hearted, try our funny or gross Would You Rather question lists. Or, if you want to keep digging deeper in the depths of somebody’s soul, here’s a list of philosophical questions to use icebreakers.

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Here’s a list of Deep Would You Rather questions

Memento mori
  1. Would you rather be infamous in history books or be forgotten after your death?
  2. Would you rather be one of the world’s leading experts in a single field or be the most well-rounded and versatile person in the world?
  3. Would you rather be stronger than average or smarter than average?
  4. Would you rather be the richest person in the world or the smartest person in the world?
  5. Would you rather eat a piece of food that was really healthy for you but tasted horrible or eat something that tasted great but was bad for you?
  6. Would you rather get to witness something once in your lifetime that few others will ever see or get to witness something once in your lifetime that many others have seen?
  7. Would you rather go through life unable to forget anything ever or go through life unable to remember anything?
  8. Would you rather have a huge imagination or a photographic memory?
  9. Would you rather have a job that pays $70 an hour but lets you work from home or a job that pays $100 an hour but requires you to be physically present?

10. Would you rather have a peaceful existence where you never had to worry about the troubles of life, or live a more “normal” life full of risk and challenge?

11. Would you rather have people admire you for your good deeds or respect you for your power?

12. Would you rather have to live out the rest of your life in the wilderness or live out the rest of your life in jail?

13. Would you rather have to spend the next 20 years as a student, or spend the next 20 years as an employee?

14. Would you rather have your entire lifetime of experiences converted into a movie that you can watch whenever you want to remember them, or your life turned into a book that can be read and interpreted by anyone?

15. Would you rather live in a country where the government is almost always doing the right thing or live in a country where they have to listen to you?

16. Would you rather live in a country where you could speak the language fluently or would you rather be able to teleport?

17. Would you rather live in a world where everyone ignores you or in a world where everyone is mean to you?

18. Would you rather live in a world where there is no crime or no privacy?

19. Would you rather live in a world with no disease or live in a world where there is income equality?

20. Would you rather live another 100 years with your body in a state of perfect health or just age normally?

21. Would you rather live to 100 years old or live to 500 years old?

22. Would you rather never be rejected ever again, or never fail ever again?

23. Would you rather never take the easy way out of anything ever again or stop procrastinating?

24. Would you rather only be able to live in a small city your entire life or only be able to live in a big city your entire life?

25. Would you rather give up all technology (cell phones, computers, etc.) or give up all movies, television, and books?

26. Would you rather be famous for all the wrong reasons or not famous at all?

27. Would you rather live in a future where people take everything too seriously or a future where people don’t take anything seriously?

28. Would you rather never have to worry about money or never be tempted to buy things you don’t need?

29. Would you rather have an exciting but dangerous life or a boring but meaningful life?

30. Would you rather be liked by everyone you’ve ever met or have everything you’ve ever wanted?

31. Would you rather be the center of attention or go unnoticed?

32. Would you rather have your books read by a few hundred people or a few million people?

33. Would you rather spend a week with someone you really admire or spend a week with someone whose company you really enjoy?