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Questions Over Dinner

Tired of small talk and chit-chat? Use this list of questions to inspire thoughtful conversations with dinner guests, friends, family, or anyone you meet.


To pick a question, take turns picking a number 1-52 and have someone else read the corresponding question. Or use this random number generator.


  1. What is something that you wish existed that would add value to your life?

  2. What is something that bothers you about how other people think?

  3. What is one thing, that if everyone did it every day, would make the world a better place?

  4. What advice would you give to a friend with ambition and a goal to help the environment?

  5. If you were to write a book, what would you title it? What would be the main points of its conclusion?

  6. What is something you did not want to do at the time, but did it anyway and are glad you did?

  7. What is the most physically difficult thing you've ever done?

  8. What ideas, habits, or realizations have most influenced your life?

  9. Did you ever have a turning point in your life, when a sudden decision or realization changed the course of your life? How did you come to that turning point and what were the lasting results?

  10. What is something you know, that you feel is unknown or under-appreciated, that could benefit humanity?

  11. What do you most regret?

  12. How long would you like to live and why? Would you want to live forever?

  13. If you died tonight, what would you want the world to know?

  14. What would you attempt if you knew you could not fail?

  15. When you think of the word “successful,” who’s the first person who comes to mind and why?

  16. What is something you believe that other people think is insane?

  17. What is the book (or books) you’ve given most as a gift?

  18. What is your favorite documentary or movie?

  19. What topic would you speak about if you were asked to give a TED talk on something outside of your main area of expertise?

  20. What is the best or most worthwhile investment you’ve made? It could be an investment of money, time, energy, or other resource. How did you decide to make the investment?

  21. Do you have a quote you live your life by or think of often?

  22. What is the worst advice you see or hear being dispensed in your world?

  23. If you could have one gigantic billboard anywhere with anything on it, what would it say?

  24. What advice would you give to your 20-year-old self? And please place where you were at the time, and what you were doing.

  25. How has a failure, or apparent failure, set you up for later success? Or, do you have a favorite failure of yours?

  26. What have you changed your mind about in the last few years? Why?

  27. What do you believe is true, even though you can’t prove it?

  28. What is the thing you have the highest certainty of?

  29. Have you ever taken 3 months off? What were the results? If you haven't yet, what would you do during those 3 months without working?

  30. How would an adult in the year 2100 describe your life and work?

  31. What inspires you?

  32. What give you hope for the future?

  33. What are 3 of your core values?

  34. What do you think the world will look like in 2100? Government, energy, art, communities, cities, buildings, etc?

  35. What do you want the world will look like in 2100? Government, energy, art, communities, cities, buildings, etc?

  36. What is your MTP (Massively Transformative Purpose)? Why? How are you currently working towards it?

  37. Will humans ever be a multi-planetary species?

  38. Who and where is your tribe?

  39. If you became unable to savor life, due to poor health or some other circumstance, would you want to continue living? Why? What would you pursue?

  40. If you were unable to do work that helps others, directly or indirectly, and could only savor life, what would you do?

  41. If you had unlimited wealth, how would you spend your time?

  42. What is one problem with capitalism?

  43. What are the greatest challenges currently facing humanity?

  44. What is humanity's greatest existential risk?

  45. How much money would you trade for your sense of sight?

  46. How related is the work you do to earn an income and your life's mission?

  47. What's your favorite place you've ever visited? Why?

  48. What's one belief you held as a child or teenager that you no longer believe to be true?

  49. Who do you want to be more like?

  50. What would you like to do in life that you feel is impossible for you?

  51. What has been your greatest adventure?

  52. What profession do we need more of in the world?


* Some of these questions are borrowed or inspired by others.


Experiment if you dare: Ask one of these questions to someone you just met with minimal small talk in advance. What were the results? Comment below.

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