No smalltalk

Smalltalk is usually boring. Here is a list of conversation questions which I think are uniformly more interesting than smalltalk. If you ever don't know what to talk about, pick one at random.

(NOTE: many of these topics were suggested by LLMs)

  1. What was a belief you held strongly in the past that has completely changed? What sparked that change?
  2. What skills or interests did you pick up during major life transitions?
  3. Which of your life experiences do you think shaped you the most?
  4. If you could master any skill instantly, what would you choose and why?
  5. What's the most valuable life advice you've received?
  6. Which culture different from your own fascinates you the most?
  7. What's the most memorable local dish you've tried while traveling?
  8. How do you think growing up in your hometown influenced who you are?
  9. What aspects of other cultures would you like to incorporate into your own life?
  10. What place exceeded or completely defied your expectations when you visited?
  11. What scientific discovery do you think would most dramatically change society?
  12. How do you think humans will evolve in the next thousand years?
  13. What mysteries of the universe intrigue you the most?
  14. If you could instantly know the answer to any scientific question, what would you ask?
  15. What technological advancement are you most looking forward to in your lifetime?
  16. How do you think technology is changing what it means to be human?
  17. What do you consider the most important qualities in maintaining long-term friendships?
  18. How do you think future generations will judge our current society?
  19. How do you balance personal ambition with contribution to society?
  20. What piece of art or media changed how you see the world?
  21. What do you think makes something "art"?
  22. Which fictional universe would you most want to live in?
  23. What do you think makes a story worth telling?
  24. What current profession do you think will be completely transformed by technology?
  25. What do you think cities will look like in 100 years?
  26. How do you think education needs to evolve?
  27. What current problem do you think humans will solve in your lifetime?
  28. What do you think are the most significant differences between generations?
  29. What traditions do you think are worth preserving?
  30. What aspects of human nature do you think will never change?
  31. What subject would you study if you had unlimited time and resources?
  32. What's a commonly accepted "fact" that you think might be wrong?
  33. What everyday object do you think needs to be completely redesigned?
  34. What innovative solution have you come up with for a daily problem?
  35. What's a brilliant design that most people don't appreciate?
  36. What do you think is the most underrated invention in history?
  37. What's your earliest memory and why do you think it stuck with you?
  38. How do you think your future self will remember this period of your life?
  39. How do you think your perception of time has changed as you've grown older?
  40. What moment in your life would you most want to relive with your current perspective?
  41. What's a small decision you made that ended up having a huge impact (ignoring "butterfly effects")?
  42. What life-changing decision did you make with very little information?
  43. What's the best way you've found to deal with uncertainty?
  44. Which parts of your personality have remained constant throughout your life?
  45. How do you think your environment has shaped who you are?
  46. What aspect of yourself would most surprise your younger self?
  47. What does authenticity mean to you?
  48. What impact would you like to leave on the world?
  49. What do you think makes a life well-lived?
  50. How has your definition of happiness evolved over time?
  51. What conditions help you think most clearly?
  52. What current practices do you think future generations will find hard to believe?
  53. What do you think is worth preserving from our current era?
  54. What's something you had to unlearn?
  55. What do you think is the next major leap in human development?
  56. If you could design a new society from scratch, what would you do differently?
  57. What do you think humans are capable of that we haven't yet realized?
  58. How do you think we could redesign education if we started fresh?
  59. What would you do if you had unlimited resources but couldn't spend them on yourself?
  60. What aspects of nature do you find most awe-inspiring?
  61. How do you think global connectivity is changing cultural identity?
  62. What period of history would you most want to experience?
  63. What technological advances do you think we're not ready for?
  64. What questions do you think are worth spending a lifetime exploring?
  65. What's a calculated risk that paid off for you?
  66. What experiences have increased your empathy?
  67. How do you know when to build and when to start over?