100 Brave and Interesting Questions

Picture of typwriter writing questions of inspiration
  1. What’s the toughest decision you made today?

  2. What’s the toughest decision you made this year?

  3. What’s the toughest decision you ever made?

  4. What have you forgotten?

  5. If you were guaranteed the answer to one question, what would it be?

  6. What’s it like being you right now?

  7. What makes you nostalgic?

  8. If you had two hours left on earth what would you do?

  9. What’s the most beautiful word in the world?

  10. Who makes you laugh more than anyone?

  11. What did your father teach you?

  12. What did your mother teach you?

  13. What’s the best gift you’ve ever given?

  14. Best gift you ever received?

  15. How many times a day do you look in the mirror?

  16. What do you bring most to a friendship?

  17. If 100 people in your age group were selected randomly, how many do you think they’d find leading a happier life than you?

  18. What is or was your best subject in school?

  19. What activity do you do that makes you feel most like yourself?

  20. What makes you feel supported?

  21. Whom do you secretly admire?

  22. What time of the day do you feel the most energetic and what do you usually do in those moments?

  23. What’s something you never leave home without?

  24. What’s a recurring dream you have?

  25. What makes you feel safe?

  26. What’s the best thing that ever happened to you?

  27. What do you want people to say about you once you’re gone?

  28. What’s the coolest thing about science?

  29. What’s the best money you ever spent?

  30. What’s a bad habit you have?

  31. What are you grateful for?

  32. Whom are you envious of?

  33. What’s an image you’ll never forget?

  34. Describe a near-death experience.

  35. If you had a clone, what would you have the clone do?

  36. What’s your idea of Heaven?

  37. What’s your idea Hell?

  38. When did you know?

  39. What can you do better?

  40. When are you most yourself?

  41. What superpower would you most like to have?

  42. If you were granted three wishes, what would you do with the second wish?

  43. What is your actual superpower?

  44. If you won 100 million dollars, what would you buy first?

  45. What's the best sound in the world?

  46. What’s perfect about your life?

  47. What song do you sing only when you’re alone and what memory does it bring back?

  48. Describe a moment you were so embarrassed you wanted to disappear.

  49. How many times a day do you think about money?

  50. Who has been the biggest influence on you in your relationship to money?

  51. What's one thing you're certain of?

  52. Describe one of your colossal failures.

  53. What makes you cringe?

  54. What does your inner voice tell you?

  55. What crime have you considered committing?

  56. What's great about your mom?

  57. What’s great about your dad?

  58. Which day would you gladly re-live?

  59. What are you awesome at?

  60. What do you want people you meet for the first time to think about you?

  61. When were you most afraid?

  62. What are you terrible at but love to do anyway?

  63. What weapon would you carry during the Zombie Apocalypse?

  64. Which of your five senses would you keep if you could only keep one?

  65. What’s something you love to make?

  66. What do you cook better than anyone?

  67. What do you wish you’d invented?

  68. What would you like to invent?

  69. Out of 100 random people, where would you rank yourself in terms of your intelligence?

  70. Where do you want to be right now?

  71. If you could be someone else for a day who would it be and why?

  72. What makes you feel powerful?

  73. What’s the meanest thing you’ve ever said?

  74. What’s the meanest thing someone has ever said to you?

  75. What three words would you have on your grave stone?

  76. What’s your first thought when you wake up?

  77. What’s one thing you wake up to in the middle of the night worrying about?

  78. If you could tell someone something anonymously, what would it be?

  79. Whom would you like to forgive and forget?

  80. If you could get rid of one of your responsibilities today, what would it be?

  81. What type of person angers you the most?

  82. What is your greatest strength?

  83. What is your worst weakness?

  84. How do you show your love for others?


Extra Brave and Interesting Questions (once trust has been established):

  1. Why are you here in this room right now?

  2. When is a time you forgave someone or were forgiven for something?

  3. What’s the biggest mistake you ever made?

  4. What are you hiding?

  5. What’s your unanswerable question--the question you seem to always be asking yourself?

  6. What are you ashamed of?

  7. What is stopping you?

  8. What’s a secret you have?

  9. How do you secretly manipulate people to get your way?

  10. When was the last time you apologized?

  11. What is the biggest lie you tell yourself?

  12. What’s the moment you left childhood behind?

  13. What's missing from your life?

  14. Do you believe in a higher power?

  15. What are you ready to let go of?

  16. What are you not saying right now?

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