List of deep questions

  1. Have you recently observed, learned or realised something which you found really surprising, profound or interesting? (it’s okay to say no)
  2. Is free will an illusion?
  3. What would life be like if the entire economy became automated?
  4. What is the most significant dream you ever had?
  5. What is one thing about yourself which you would like to change but is proving hard to change?
  6. What has really helped you to overcome a past negative belief, pattern or habit?
  7. What do many people not know about themselves?
  8. Does God exist?
  9. What is a fundamental aspect of reality that you see differently from others and why?
  10. What are some of the most significant ways in which culture is changing for the better/worse?
  11. Is there any really good evidence of the paranormal or higher spiritual dimensions of reality?
  12. What one piece of advice would give your younger self?
  13. If you became the dictator of a small island what kind of regime might you enforce?
  14. Are relationships essentially transactional?
  15. Is there any specific type of discomfort which you are currently learning from in life?
  16. What is human nature?
  17. Will technological advances wipe out humanity?
  18. Who are you really?
  19. Has any book, article or podcast changed how you think about life and how?
  20. If you could change one thing about your culture, what would it be?
  21. What is needed to bring humanity closer together?
  22. Could an open borders society work in practice?
  23. What are the most likely ways for the human race to be wiped out?
  24. Will computers ever be fully conscious?
  25. How would you explain different people’s experiences of God?
  26. What experience has most made you who you are?
  27. Which parts of you are most in conflict?
  28. To what might you attribute your biggest successes and failures in life?
  29. Where is history heading?
  30. What’s the key to solving life’s problems?
  31. What does it mean to be self-actualised?
  32. What would you most want to know about yourself if you could?
  33. Is there anything that you can’t joke about?
  34. What social stigma does society need to get over?
  35. What do you think many people are brainwashed about?
  36. How do you judge people?
  37. What are the greatest flaws in human nature?
  38. What about the opposite sex confuses you the most?
  39. What is a negative pattern you have overcome in life?
  40. What’s one of the most awkward things that happens to you on a regular basis?
  41. What aspects of life or yourself are you only beginning to understand?
  42. What is love?
  43. What is truth?
  44. What values are most important to you?
  45. What is your life’s greatest challenge?
  46. If you could have any magic power, what would it be?
  47. What is one of the main driving forces in your life?
  48. What is one of the questions to which you would most want the answer?
  49. Could a loving god have created this world?
  50. What gives life its meaning?
  51. Why do we dream?
  52. Why do we experience emotion?
  53. Is the answer to this question “no”?
  54. Is there such a thing as fate?
  55. What is the source of morality
  56. Do you think there is intelligent life in the universe?
  57. Is eating meat ethically defensible?
  58. What factors complicate personal interactions and relationships?
  59. What is religious faith?
  60. Will religions like Christianity and Islam still exist in 500 years?
  61. Have you ever had a recurring dream and what meaning would you give it?
  62. Is torture ever justified?
  63. What will people and society be like if average life expectancy ever goes up to a few hundred years?
  64. What harsh truths do you prefer to ignore?
  65. Does who we are change depending on who we are talking to?
  66. Is the self an illusion?
  67. Would you rather live in a simulation if it made you happier?
  68. Could you fall in love with a robot knowing that it wasn’t conscious?
  69. What two questions would you ask to get the most information about who a person truly is?
  70. Why do we judge ourselves by our intentions but judge others by their actions?
  71. How would you defend the human race if we were put on trial by an advanced species of aliens?
  72. At what point would violently overthrowing a government become ethical?
  73. What do you often notice about other people which they are unaware of?
  74. If babies are considered innocent, when do people cease to be innocent?
  75. What drives people to commit evil acts?
  76. What does your inner voice tell you?
  77. What words would you use to describe the human race?
  78. What are your strongest beliefs about?
  79. How do you lie to yourself?
  80. When you look at the world, what is most fascinating to you?
  81. What things do you wish were easier to say to people?
  82. Do you believe that everything happens for a reason?
  83. Why is there so much chaos and suffering in the world?
  84. If the Universe were a simulation, what might the point be?
  85. In what ways are we all connected?
  86. What would life be like if everyone could read each others’ minds?
  87. What do you think your last thoughts will be before you die?
  88. If you could invent any piece of technology, what would it do?
  89. What message would you place in a time capsule to discovered by a different future civilisation?
  90. What is the best advice you ever received?
  91. What stops people from connecting with each other?
  92. What are you most committed to in your life and why?
  93. How much effort should an individual put into not offending others?
  94. What qualities or beliefs do you find annoying in others and why?
  95. What is one of the most common and yet irritating mistakes that people make with you?
  96. What is the main source of your moments of unhappiness?
  97. What do people sometimes misunderstand about you and why?
  98. Were there any past situations in which you wish you had communicated very differently and why?
  99. To what extent can people be understood through personality types?
  100. Do you have an irrational fear of anything?
  101. What is something you think everyone should do at least once in their lives?
  102. What is freedom?
  103. Is it wrong to be a billionaire?
  104. What do you like the most about people?
  105. What do you dislike the most about people?
  106. How do you forgive people for their worst actions?
  107. Are cultural stereotypes or generalisations valid to some degree?
  108. What are some of the best and worst things about various cultures?
  109. Should we intervene to stop cultural practices like FGM or infant male circumcision?

Two questions to think about for future events:

  1. What deep or fundamental question would you be most willing to explore over the next few months, carrying out a little research on the side to help you get closer to the truth?
  2. What fun and fascinating topic would you be most interested in hearing an expert talk to you about, with the option of being able to pick their brain, ask them whatever questions you like and get answers that rapidly enhance your learning?

Or just for fun

  • Briefly us about one of your weirdest, most surprising or funniest [choose from the following: dreams / life experiences / discoveries about other people / discoveries about other cultures]
  • What is the funniest thing you do when no one is watching?
  • What’s the weirdest thing you can imagine?
  • What is the most exciting death you might choose?
  • What would a world populated by clones of you be like?
  • What do most people look stupid doing?
  • Would you enjoy watching a movie of your life?
  • Which set of items could you buy to make a cashier feel uncomfortable?
  • What is the weirdest thing you have seen in someone’s home?
  • What is the most imaginative insult you can come up with?
  • What would be the creepiest thing you could say while passing a stranger on the street?

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