This is old news, but apparently there are thirty-six questions you can ask someone new to your life to build a foundation of personal intimacy, and they’re…okay. They’re better than the usual ones you stammer out in a bar or on your online dating profile or across the Pokemon table at the local game store.

But they’re not as good as mine. I guarantee that if you sit across from someone and ask/answer these questions, you will know the depths of each other’s hearts by the final one.

  1. The three required elements of a perfect day are: ______, ______, and _____.
  2. People who don’t use the Oxford comma are _____.
  3. People who use two spaces after a period are _____.
  4. The optimum place to live is close to the beach | the mountains.
  5. When you are debriefed in the afterlife, what truth do you most want to know?
  6. Do you believe in ghosts? Why or why not?
  7. What do you wish you had told someone before they died?
  8. What do you wish someone had told YOU before they died?
  9. What song would you send to space as the perfect representation of humanity?
  10. What book most changed your life?
  11. What movie most changed your life?
  12. If you could travel in time and stop one book from being written, which would it be?
  13. What day would you erase from your memory?
  14. What message of ten words or less would you send back to yourself in time?
  15. To what historical era do you think your personality is best suited?
  16. What is your go-to Freudian defense mechanism (repression | regression | reaction formation | projection | sublimation)?
  17. What does everyone else think is a flaw in someone’s appearance that you actually like?
  18. What does everyone else think is a flaw in someone’s personality that you actually like?
  19. You have thirty seconds to name a baby, a kitten, an infectious disease, and a battleship. What names do you choose?
  20. Which convicted member of the Manson family is LEAST morally culpable? Why?
  21. Who is the most overrated serial killer in history? Why?
  22. Lee Harvey Oswald did | did not act alone.
  23. D.B. Cooper did | did not survive his jump.
  24. What three convictions (historical or contemporary) would you pardon with executive power?
  25. After the collapse of society, what is your chosen weapon?
  26. Who was (or would have been) America’s greatest president?
  27. What amendment would you add to the constitution?
  28. What burning cultural question of the day do you truly not give a shit about?
  29. If you could design a recreational drug, what would it do?
  30. What is the worst decision you ever made?
  31. What is the best decision you ever made?
  32. Who has paid the highest cost for your success?
  33. What profession would have been perfect for you?
  34. What do you believe to be true without evidence?
  35. What is the least redeemable sin?
  36. What is the greatest possible virtue?