30 Questions for a Deeper Conversation in 2018

Questions tend to reveal someone’s values, qualities, fears, and personal past.  When you are sitting in a bunch, and you feel that the environment is so shallow, that a fish will die in it, it is time to ask some deep questions.

Here are some deep questions you can ask, relevant to our time:

  1. What is your most irrational fear for the country?
  2. What is your most rational fear for the country?
  3. How do you think you will die?
  4. What’s the biggest risk you have ever taken that didn’t pay off?
  5. What is a big risk you have taken that did pay off?
  6. Do you have weird habits? How do you think you developed?
  7. Do you wish you were raised differently? Why?
  8. What is one thing you wish you were good at?
  9. What’s your favorite childhood memory?
  10. How do you think you changed after September 11, 2001?
  11. If now is your last moment, would you be proud and satisfied with how you lived your life?
  12. What do you consider to be your greatest accomplishment in life?
  13. What mistake or memory keeps you up at night?
  14. When was the last time you cried?
  15. Who do you wish the president is?
  16. If you were God, and humans were created, how would you create a human differently?
  17. What would you title your memoir?
  18. Did you ever get detention or suspension from school for anything? What was the story?
  19. If you could have a time machine for a week, what three eras would you visit and who would you be? Why?
  20. What are your simple pleasures in life?
  21. Would your younger self be proud of who you are today?
  22. When you were little, what did you want to be when you grew up?
  23. When was the last time you laughed until you cried?
  24. What or who did your parents name you after? What’s your relationship like to your name?
  25. If you could have a cup of coffee with anyone dead or alive, who would it be?
  26. Anything you’ve been too afraid to say out loud to someone?
  27. If you were to change something in how our government works, what would it be?
  28. Where do you see yourself in the spectrum of the Two Party system?
  29. If you were stranded on an island with one person, who would you like it to be?
  30. What would you say your 5 deepest values?


Wissam Charafeddine



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