Level 4 · 25 / 30

Who have you failed, and do they know it?

Who have you failed, and do they know it?

Questions for skipping small talk. Start anywhere; go as deep as the other person lets you.

More at this level

  1. Is there a belief that's useful to hold and false?
  2. What do you think happens when we die, and does it change how you live?
  3. What would you want people to say about you when you're not in the room?
  4. What's the thing you've never told anyone, or the closest thing to it you can say?
  5. What do you think I've got wrong about you so far?
  6. What do you hope is true?
  7. If you had one phone call left, who would you call, and what would you say?
  8. What's the loneliest you've ever been?