Around The Table

101 ways to kick off the best family dinner table game.

Nick Crocker
Nick Crocker
Published in
6 min readJun 28, 2014


Whenever my family gets together for dinner, we play a game called Around The Table. It’s so simple, it’s barely worthy of the ‘game’ title, but it’s pretty amazing what happens when you play.

The rules are simple:

  • Someone picks a question.
  • Everyone at the table takes turns to answer the question.
  • Listeners can’t interrupt, interject or have side conversations. They just have to listen.

The first remarkable part of Around The Table is that you discover everyone, when given a chance, has the ability to be a great storyteller.

The second remarkable part of the game is that EVERYONE has a story to tell.

The game works only if you pick good questions. Good questions are hard to find, you might have to play a few times to get a feel for what kind of questions work at your table.

To get you started, here’s a list of 101 questions that you can use to kick things off.

Don’t think too much about it. Get one person at the table to pick a number, at random, between 1-101, ask the question and just start listening.


  1. Are you happy with your life for the most part right now?
  2. At what point in your life did you realise you’d become an adult?
  3. Describe something that’s happened in your life for which you have no explanation.
  4. Describe your biggest failure so far.
  5. Do you remember your favorite teacher? Tell us about them.
  6. Do you think you control your own destiny? Give an example from your life to validate this.
  7. For what in your life do you feel most grateful?
  8. Give me an example where you sought to improve yourself in the past few years.
  9. Growing up, what was the thing you did that got you into the most trouble?
  10. What is something powerful you learnt from your mother?
  11. How do you recharge?
  12. How do you see your life 10 years from now? You’ll be __.
  13. How do you think your childhood compares to other people’s?
  14. How do you think your coworkers see you?
  15. How would you explain your basic life philosophy?
  16. How would your peers have described you in high school?
  17. If money was no object, what would you do differently?
  18. If we’re sitting here a year from now celebrating what a great year it’s been for you in this role, what did you achieve?
  19. If you could go back and be any age for a week, what age would that be?
  20. If you could change anything about the way you were raised, what would it be?
  21. If you could go back in time, what year would you travel to?
  22. If you could have personally witnessed any historical event, what would you want to have seen and why?
  23. If you found out today you were going to die in a year, what would you do differently tomorrow?
  24. If you had to work on only one project for the next year, what would it be?
  25. If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?
  26. If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone?
  27. If you were to tell one person “Thank You” for helping me become the person I am today, who would it be and what did they do?
  28. If you were to tell one person “Thank You” for helping me become the person I am today, who would be someone who would not expect it and what did they do?
  29. Name the most terrifying moment of your life so far?
  30. Tell me about a mistake that you made, either work or personal, that taught you a significant lesson?
  31. Take three minutes to describe what your life was like growing up?
  32. Tell me about someone you envy?
  33. Tell me about someone you really admire?
  34. Tell me about something you really regret?
  35. Tell me about the worst punishment you had when you were a child?
  36. Tell the story of something bad that happened to you that turned out to be for the best?
  37. Tell us about a time when things didn’t go the way you wanted or a project that didn’t turn out how you had hoped.
  38. What movie/TV show/creative work has had the most impact on your life?
  39. What accomplishment are you most proud of?
  40. What are three things in your life that make you really happy?
  41. What are you most proud of?
  42. What characteristic do you most admire in others?
  43. What do you like least about yourself?
  44. What do you miss most about being a child?
  45. What do you most love about your life?
  46. What do you most love about yourself?
  47. What do you wish you had more time to do?
  48. What does your life say about you?
  49. What embarrasses you about yourself?
  50. What has been the hardest thing you’ve had to do?
  51. What has been your biggest challenge?
  52. What have been the happiest times in your life?
  53. What is most uncertain in your future?
  54. What is something you learned in the past year?
  55. What is the greatest accomplishment of your life?
  56. What is the habit you are proudest of breaking?
  57. What is the most memorable class you have ever taken or lesson you have ever learned?
  58. What is the strangest thing you have ever eaten? Describe how you came to be eating it.
  59. What is the thing in your life that most makes you sad?
  60. What is the toughest job you have ever had? How did you handle it?
  61. What is your biggest success up until now?
  62. What is your favorite memory?
  63. What is your greatest strength and greatest weakness?
  64. What is the most terrible memory you’re willing to share?
  65. What is your wildest dream? What sits at the edge of possible, but at the beginning of impossible?
  66. What kind of boss do you work best with? What kind of boss do you aspire to be?
  67. What kind of holidays do you like? Which holiday has most resembled your ideal?
  68. What kind of impact do you believe you have on people?
  69. What more are you wanting in your career right now?
  70. What movie or novel character do you most identify with?
  71. What one thing about you do you want in your eulogy?
  72. What one thing would you change if you had to do it over?
  73. What quality in you would you hate to see emulated in your children?
  74. What story would your best friend/brother/partner/sister/mother/father tell about you if someone asked her to tell a memorable one?
  75. What was the last experience that made you a stronger person?
  76. What would you be doing if you weren’t at your current job?
  77. What would you most regret not having done by the end of your life?
  78. What’s the best compliment you have received?
  79. What’s something most people don’t know about you?
  80. What’s something you wish everyone knew about you?
  81. What’s the best decision you ever made?
  82. What’s the best gift you’ve ever given? What’s the worst gift you’ve ever given?
  83. What’s the best gift you’ve ever received?
  84. What’s the biggest personal change you’ve ever made?
  85. What’s the highest leverage use of your time and talent?
  86. What’s the most important lesson you’ve learned in the last year?
  87. What’s the scariest thing you’ve ever done? What’s the scaredest you’ve ever been?
  88. What’s the most money you’ve ever lost?
  89. What’s the sickest you have ever been?
  90. What’s the stupidest thing you’ve ever done?
  91. What’s your earliest memory?
  92. When have you been most satisfied in your life?
  93. When you look at a restaurant menu, what items are you scanning for and why?
  94. When you think about your future, what most scares you?
  95. Where do you most want to travel, but have never been? (Pick a Top 3)
  96. Which are the ‘other lives’ that torture you most?
  97. Who in your life has influenced you the most? How did they do it?
  98. Who is your hero? Who is your role model, and why?
  99. Who’s your best friend? Give an example of how special they are.
  100. Would you recommend your career to other people? Why / Why not?
  101. Your house, containing everything you own, catches fire. You have time to safely save any one item. What would it be?



Nick Crocker
Nick Crocker

General Partner @BlackbirdVC. Sequencing the journey to build strength along the way.