Here are a list of questions that serve as useful prompts in random conversations. Usually, it's better not to ask these questions verbatim, but conversations can go well when questions that have this shape are asked:

  • What's one story from your life that people need to hear in order to know who you are?
  • What beliefs do you have that your peers think are absurd?
  • Which personality trait do you think would it would be better to have more of on the margin?
  • What's a common delusion that you wish was more prevalent?
  • Do you think the world is getting better over time overall? Do you believe in progress?
  • Do you think you are getting better?
  • What do you think is true that everyone else also thinks is true?
  • What's a silly thing you did in the past that you are most proud of?
  • What do people misunderstand about you when they first meet you? What do your best friends know about you that your acquaintances don't?
  • What's something that people misunderstand about X?
  • What is on your friends' minds right now?
  • What's something that you love doing that you're bad at? What's something that you're good at, but you love doing?
  • What belief do you have that is closest to a conspiracy theory?
  • What's something that nobody will tell me that I should know?
  • How do you get stuff done?
  • What would your younger self think about your older self?
  • What do you wish more people knew about you?
  • What kind of environment do you thrive in? Why?
  • What kind of prestige do you care about?
  • What were some of the choices that your great-grandparents had to make that contributed to your family's story?
  • If they're from somewhere else, what makes the culture at X better or worse than the culture here. What parts of it, if any, do you miss?

I took some of these questions from here and other places I don't recall.

If I should add a question to this list, let me know.

Thanks to Ivie Crawford, Ashe Kabash, and Thomas Hollands for suggestions.