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PSST: Want to work together more closely?


101 Questions For Meaningful, FUN, Satisfying Connection + Conversation

Hi, I’m Alex!

If you need a little help to start playing by your own rules, there’s a few ways we can work together more closely.


Last year I sifted through the workbooks and trainings from my 19 years in positive psychology and coaching, and put together this list of questions. Family gatherings, vacations, or holiday meals can bring joy, but they can also bring strife. Perhaps a guided conversation will spark the kind of meaningful connection we dream about, but rarely enjoy.

A dear friend wrote to me over her Christmas family vacation that the list helped her turn a group of sullen, grouchy teens and kids into a giggling, connected family.

Feel free to print it out, share the link, or read it out loud from your phone. I hope you have a beautiful gathering, no matter where you are, or what you’re celebrating.

  1. What was your favorite surprise in the last year?
  2. What’s a secret thing you love that everyone else thinks is dumb?
  3. What artist or creative person do you admire most, and why?
  4. What have you taken a stand for in this life?
  5. What’s a favorite book you’ve read more than once?
  6. What movies have you watched more than 3 times? 10 time?
  7. What’s your favorite thing to do in the morning?
  8. What’s a cool way to make New Year’s resolutions you’d like to try?
  9. Would you be willing to give up your cell phone for 1 year in exchange for $100,000?
  10. Who is one person who taught you something really important and what impact it had on your life?
  11. What’s a time when you were really brave?
  12. What would your dream home look like?
  13. If you could go to any live music concert in time, who would be performing?
  14. What country or place would you love to visit and stay for a whole month? Why?
  15. If you could make a documentary, what would it be about?
  16. If you could invent a national holiday, what would it be?
  17. Who are three people you’d love to have dinner with?
  18. What sport do you wish was in the Olympics?
  19. If you could have any animal as a pet for one day, what would it be?
  20. If you could change one thing about the world, what would it be?
  21. If you had $10 Million to give to any good causes, what would they be?
  22. Who makes you laugh more than anyone else?
  23. What’s your favorite family tradition?
  24. What’s a chore you secretly enjoy doing?
  25. What’s a chore you would gladly pay someone else to do?
  26. What 3 languages do you wish you could speak fluently and why?
  27. What would you do if you found a suitcase full of cash on the street?
  28. What’s your favorite thing about yourself?
  29. What’s the craziest dream you ever had?
  30. Have you ever experienced magic? What happened?
  31. If I gave you $50 to spend on yourself today what would you do?
  32. Do you consider yourself a trouble maker or a smoother over? Both?
  33. What would you tell the President if you were in the room with him?
  34. What’s something you want to learn how to do before you die?
  35. What’s one strength or characteristic you admire in someone else but don’t really believe you can master?
  36. If you could go to the Olympics for one sport what would it be?
  37. Who was your first best friend? What was something fun you remember about them?
  38. If you could time travel would you go forward or backward? When? Why?
  39. When do you feel most loved?
  40. What’s something you’re committed to never doing?
  41. What’s a social justice cause you’re very committed to?
  42. What’s your favorite season and why?
  43. If you could play an instrument like a pro, what would it be?
  44. If you could have any super hero power what would it be?
  45. What was a time when you did the right thing even though it was really hard?
  46. If you had a three-legged dog, what would you name it?
  47. What qualities make a good friend?
  48. If you could give everyone in your country a gift, what would it be?
  49. How do you help yourself feel better when you’re sad?
  50. What inspires you most about your family?
  51. If you were going to make a feast for your family, with kitchen helpers and all the ingredients you want, what would you make?
  52. What survival skills do you think are important for a zombie apocalypse?
  53. If you could be a guest star on any TV show in history what would it be?
  54. If you could be a great dancer, what kind of dance would be expert at?
  55. What was your favorite cartoon growing up?
  56. If your pet could talk what would they say?
  57. If you could read someone’s mind, whose mind would you read?
  58. What would you first do if you suddenly had the power to become invisible?
  59. Why do you think people become bullies?
  60. If you could create one law, what would it be?
  61. What do you want to be remembered for?
  62. If you could only be one age for the rest of your life, what age would you be?
  63. Would you rather be the funniest person in the world or the smartest? Why?
  64. What was your favorite family vacation so far?
  65. If you had to rename yourself, what name would you pick?
  66. What does success mean to you?
  67. Name a bad habit you have: if you didn’t have that habit, how would your life be different?
  68. What do you need most right now?
  69. What’s the coolest thing you’re working on right now?
  70. What’s your favorite book of the last year?
  71. Who would you like to swap places with for a day and why?
  72. What’s the most memorable meal you’ve ever had?
  73. What are your top pet peeves?
  74. What’s a secret talent no one knows about you?
  75. What’s a super hero you’d create, and what would be their powers?
  76. What brings you joy?
  77. What habits help you be your best?
  78. What’s missing from your life? From the world?
  79. How do you inspire others?
  80. What do you wish you had more time to do?
  81. What do you hope for yourself in 5 years?
  82. If you could invent something what would it be? (no magic wands or time machines!)
  83. What makes you lose track of time?
  84. What do people ask your help for?
  85. What’s something you accomplished in the past that you’re proud of?
  86. What do you want your funeral to be like?
  87. What gives you strength?
  88. What’s your kryptonite?
  89. A stylist notices a complicated hairstyle, a singer notices a talented vocalist… what do you notice?
  90. What do you love to learn about?
  91. Who is your idol?
  92. You’re in an elevator, alone with your hero. You have 90 seconds to tell them about yourself. What do you say?
  93. What could you do all day and not consider it a waste of time?
  94. What one thing would you find a way to do, no matter what?
  95. You’re in an elevator with your hero. You have 90 seconds to tell them about yourself. What do you say?
  96. You’re given one wish… but you can’t use it on yourself. What would you wish for?
  97. If you got to create your own job, what would it look like?
  98. If you could receive an unrestricted, unlimited grant to complete one project, what would that project be?
  99. What book do you really want to write?
  100. What gives you peace of mind?
  101. What do you geek out about?
  102. Why are you here in this lifetime?