Fun Friday: Questions for Conversations with Friends

Stealing a bit from Fred Wilson, today is going to be Fun Friday.

Here’s some good questions to have more interesting conversations with friends (and to get to know them better!)

  1. You have to go on a road-trip from Maine to San Diego CA. You have to bring 3 people. Who are they?
  2. Which nicknames have you been called?
  3. What about yourself are you really self-conscious about?
  4. If you had someone following you around all the time what would you have them do?
  5. What is your favorite body part about yourself?
  6. If you had kids would you want them to be smart or good looking?
  7. What’s the favorite thing you’ve bought this year?
  8. What would be the most surprising scientific discovery imaginable?
  9. If you were to do a city wide poll, what would you want to learn?
  10. What’s the worst job you’ve ever had?
  11. We look back now at slavery and are appalled and shocked. What will people look back at us 50 years from now and be shocked and appalled by?
  12. What is something you’ve never told anyone, not because it’s a secret but because you’ve just never told anyone?
  13. What are you curious about?
  14. What’s one bad habit you’re trying to get rid of?
  15. If you can instantly become, what would you want to be an expert in?
  16. If you could be guaranteed one thing in life (besides money), what would it be?
  17. What’s something you believe that almost everyone else disagrees with you about?
  18. If you could live life over again, would you sleep with more people or less? Why?
  19. If you were to die tomorrow, what little thing would you regret not doing?
  20. What normal superpower would you have?
  21. If you could send a message to the entire world, what would you say in 30 seconds?
  22. If you could ask one person one question and they had to answer truthfully, who and what would you ask?
  23. If you had to teach a class on one thing, what would you teach?
  24. If you could change one thing about your life instantly, what would it be?
  25. What feeling do you most wish the English language had a word for but it doesn’t? Describe the last time you felt that way.
  26. What’s the best piece of advice you’ve ever been given?
  27. When you die, what do you want to be remembered for?
  28. Someone gets a text message from you and for whatever reason they’re not sure it’s actually you. They’re worried someone stole your phone. What could they ask to make sure it’s actually you?
  29. What’s something you used to strongly believe that you now think you were fundamentally misguided about?
  30. When you think about success, who comes to mind and why?
  31. Who was your first kiss?
  32. Who did you lose your virginity to?
  33. Have you ever cheated?
  34. What are your showers like?
  35. What is something you like that most people don’t?
  36. What is something most people like that you don’t?
  37. What’s left on your bucket list?
  38. What was your first screen name?
  39. What’d your parents do well and what would you change?
  40. If you could undo 1 moment in your life?
  41. Have you ever been scammed?
  42. Start over at 18 knowing everything you know now. What would you do differently?
  43. When were your parents most disappointed in you?
  44. You can have someone full-time remind you something every day; what would you want?
  45. Which band / artist – dead or alive would play at your funeral?
  46. What 3 words would your friends describe you?
  47. What was your high school superlative?
  48. What was the first book you read that changed your mind?
  49. Brag to me about the best things going on in the past 30 days.
  50. Who’d play you in a movie?
  51. You have $5,000 to spend on someone you love, what would you do with the money?
  52. What book belongs on everyone’s bookshelf?
  53. If there was a sandwich named after you what would be on it?
  54. Last time you lost your temper?
  55. If you could travel back in time to one place or one incident what would it be..and Why?
  56. What’s your best scar or birthmark story?
  57. If you had to delete all but 3 apps from your smartphone, which ones would you keep?
  58. What are you most excited about right now?
  59. What is 1 thing that I don’t know about you?
  60. My pet peeve is…
  61. Have you been to therapy–why? If no, why not?
  62. What are 3 adjectives to describe each of your parents
  63. Buried or cremated?
  64. What would be your best day ever?
  65. What day would you want to repeat forever?
  66. What’s a compliment someone gave you still think about?

(Originally put together by Justin Mares and Noah Kagan, with updates from me).