Charles McCool
1 min readApr 3, 2023

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Twenty questions you can ask anybody to start a conversation

— from Peter Shankman newsletter today (3 April 2023)

  1. Did you listen to anything interesting today?
  2. If you could do any part of today over again, what would it be?
  3. How much coffee did you drink today?
  4. Will you remember any specific part of today a vear from now? Five years?
  5. Did you take any photos today? What did you photograph?
  6. What app did you open most today?
  7. How can I make your day easier in 5 minutes?
  8. If we were leaving for vacation tonight, where do you wish we would be heading?
  9. If you won $500 and had to spend it on yourself, what would you buy?
  10. If your day was turned into a movie, who would you cast?
  11. What did you say today that you could have never expected to come out of your mouth?
  12. What did you do to take care of yourself today?
  13. When did you feel appreciated today?
  14. If you could guarantee one thing for tomorrow what would it be?
  15. If we traded places tomorrow what advice would you give me for the day?
  16. What made you laugh today?
  17. Imagine committing the next year to learning one thing in your spare time. What would it be?
  18. Did you give anyone side-eye today? What did they do to deserve it?
  19. What do you wish you did more of today?
  20. What do you wish you did less of today?

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