100 questions to get to know anyone better

Have you ever ran out of conversation with a friend?

Are you tired of talking about the weather and never get to know people a little bit better?

You’d be surprised at the incredible amount of things you never knew about even your closest friends or relatives.

This week I challenge you to ask a friend as many of the questions below.

And while you are it, you may as well answer some of them yourself.

Last night while having dinner I went down the list with my wife.

I’ve known her for 9 years and I thought we already knew everything about each other.

I was wrong.  After 2 hours we only got down the first 20 questions.

Each of us is an entire different world. Questions are an amazing tool to help you explore those worlds.

Questions show that you care too. You should worry when you stop asking questions. Maybe you stopped being interested in that person or maybe you simply ran out of questions to ask.

If that’s the case, here you have 100 opportunities to get to know anyone a little bit better:

  1. What is one article of clothing that someone could wear that would make you walk out on a date with them?
  2. If you had someone following you around all the time what would you have them do?
  3. What is your favorite body part about yourself?
  4. If you had kids would you want them to be smart or good looking?
  5. What’s the favorite thing you’ve bought this year?
  6. What would be the most surprising scientific discovery imaginable?
  7. If you were to do a city wide poll, what would you want to learn?
  8. What’s the worst job you’ve ever had?
  9. 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?
  10. What is something you’ve never told anyone, not because it’s a secret but because you’ve just never told anyone?
  11. What are you curious about?
  12. What’s one bad habit you’re trying to get rid of?
  13. What’s one thing you believe that almost nobody else does?
  14. If you can instantly become, what would you want to be an expert in?
  15. If you could be guaranteed one thing in life (besides money), what would it be?
  16. What’s something you believe that almost everyone else disagrees with you about?
  17. If you could live life over again, would you sleep with more people or less? Why?
  18. If you were to die tomorrow, what little thing would you regret not doing?
  19. What normal superpower would you have?
  20. If you could send a message to the entire world, what would you say in 30 seconds?
  21. If you could ask one person one question and they had to answer truthfully, who and what would you ask?
  22. If you had to teach a class on one thing, what would you teach?
  23. If you could change one thing about your life instantly, what would it be?
  24. 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.
  25. What’s the best piece of advice you’ve ever been given?
  26. When you die, what do you want to be remembered for?
  27. 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?
  28. What’s something you used to strongly believe that you now think you were fundamentally misguided about?
  29. When you think about success, who comes to mind and why?
  30. Who was your first kiss?
  31. Who did you lose your virginity to?
  32. Have you ever cheated?
  33. What are your showers like?
  34. What is something you like that most people don’t?
  35. What’s left on your bucket list?
  36. What’s your recurring nightmare?
  37. What was your first screen name?
  38. Did you do family dinners? How were they?
  39. Last time you ate at McDonald’s?
  40. What’d your parents do well and what would you change
  41. If you could undo 1 moment in your life?
  42. Have you ever been scammed?
  43. Start over at 18 knowing everything you know now. What would you do differently?
  44. Would you rather live forever or colonize a planet?
  45. When were your parents most disappointed in you?
  46. You can have someone full-time remind you something every day; what would you want?
  47. Which band / artist – dead or alive would play at your funeral?
  48. What is your spirit animal?
  49. What 3 words would your friends describe you?
  50. What was your high school superlative?
  51. What was the first book you read that changed your mind?
  52. Brag to me about the best things going on in the past 30 days.
  53. Who’d play you in a movie?
  54. Which nicknames have you been called?
  55. You have $5,000 to spend on someone you love, what would you do with the money?
  56. What book belongs on everyone’s bookshelf?
  57. You have to go on a road-trip from Maine to San Diego CA. You have to bring 3 people. Who are they?
  58. If there was a sandwich named after you what would be on it?
  59. Last time you lost your temper?
  60. If you could travel back in time to one place or one incident what would it be..and Why?
  61. What’s your best scar or birthmark story?
  62. If you had to delete all but 3 apps from your smartphone, which ones would you keep?
  63. What are you most excited about right now?
  64. What is 1 thing that I don’t know about you?
  65. You have 1 day to spend 1 million dollars, what do you do?
  66. My pet peeve is…
  67. What about yourself are you really self-conscious about
  68. Have you been to therapy–why? If no, why not?
  69. What are 3 adjectives to describe each of your parents
  70. You have $100k. You have to donate or create a charity, what do you do?
  71. What are you really good at?
  72. How would you commit suicide?
  73. Buried or cremated?
  74. What would be your best day ever?
  75. What day would you want to repeat forever?
  76. What’s a compliment someone gave you still think about?
  77. How do you deal with adversity?
  78. Have you ever been in a physical fight?
  79. Have you ever met a celebrity?
  80. What is your highest achievement?
  81. What purchase has made the biggest difference in your life?
  82. Who has been the most influential person in your life?
  83. Do you believe in life after death?
  84. What is the most amazing thing you’ve gotten away with?
  85. What was your favorite subject at school?
  86. Describe one of the happiest moments in your life
  87. What’s the most trouble you’ve gotten into?
  88. What do you enjoy most doing?
  89. What is the biggest lie you’ve ever told?
  90. What is one thing you regret not doing?
  91. What was a very embarrassing moment?
  92. When have you laughed the most?
  93. When have you cried the most?
  94. Who have you been the most jealous of?
  95. What is the nicest thing you’ve done?
  96. What is the book, person, movie that has influenced you the most?
  97. Have you ever been attracted to a person of the sex you are not most commonly associated with?
  98. What’s your favorite game?
  99. What has been your cheapest and most rewarding investment?
  100. When was the last time you thanked someone special for being part of your life?

BONUS: What would you wish people asked you more often?

Let me know if you try this challenge. I’d love to know if it was useful, fun, awkward, or whatever.

Also, please feel free to suggest any other questions.

I’ll be storing all questions HERE.

Peace, Love, and Cookies,

P.S: Original question list by Justin Mares and Noah Kagan.  All questions after #76 are mine.

P.2: Don’t like the questions? No problem. This exercise can get exponentially more fun/dangerous/interesting after a couple glasses of wine 😉

P.3: If you missed last week’s email you can read it HERE.


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