Self-growth · Quiet

Deep.60 deep questions to ask

Questions about freedom, regret and what makes a life feel full.

25–40 min 60 cards Solo or 1–2
What's inside
MeaningDeathHappinessHuman NatureChangeFreedomLove+51 more
Sample card

What did you have to lose before you could grow?

About the Deep deck

Deep is the deck for questions you would rarely ask across a crowded table. What would you keep doing even if it never added up to anything? What did you have to lose before you could grow? What would someone have to do for you to never forgive them?

These take time. Pick one or two for an evening, ask them one to one, and answer your own question too. Nobody wants to be the only person opening up.

All 60 deep questions to ask

  1. What would you keep doing even if it never added up to anything?

  2. When did death stop being an abstract idea for you?

  3. When were you last happy without noticing it at the time?

  4. Tell me about a time you saw someone be good when no one was watching.

  5. What has been the turning point in your life that changed everything?

  6. What does freedom mean to you?

  7. What has loving someone cost you?

  8. If time wasn't money, what would you spend your time on?

  9. What truth are you protecting someone from right now?

  10. What kind of mark do you want to leave on the world?

  11. How much of where you ended up was actually your decision?

  12. When did someone last understand you without you explaining?

  13. What prevents you from living a full life?

  14. Which mistake of yours are you still paying for?

  15. What do you think about a higher power?

  16. Who are you, if your name, job, and relationships are taken away?

  17. When has being alone been the best thing for you?

  18. What's the most unfair thing you've made peace with?

  19. What did you want badly ten years ago that you don't want now?

  20. How do you know when you've actually forgiven someone?

  21. What did you have to lose before you could grow?

  22. How do you define success without money?

  23. Whose happiness do you carry that isn't yours to carry?

  24. What is the most beautiful thing you have ever seen?

  25. What are you most afraid your phone is doing to you?

  26. Who knows you better than anyone you've ever dated?

  27. Describe a time your gut was right and you ignored it.

  28. What is the biggest lesson you have learned about humility?

  29. Where do you find inner peace?

  30. What would you ask the universe if you could get one answer?

  31. Who do you still want to see get what they deserve?

  32. What do you tell yourself that you know isn't quite true?

  33. What is humanity's greatest achievement?

  34. Which feeling do you try hardest to hide from people?

  35. What loss do you fear the most?

  36. Describe someone you watched change once they got power.

  37. What is a prejudice you would like to get rid of?

  38. Which memory would you delete if deleting it was permanent?

  39. For what cause would you be ready to die?

  40. How would your life have to change before you'd call it a good one?

  41. A machine tells you it's afraid. What do you owe it?

  42. What makes us human?

  43. Which year of your life do you keep going back to in your head?

  44. We are all addicted to something—what are you addicted to?

  45. What do you know now that you'd give back if you could?

  46. What is the biggest risk you have taken (or left untaken)?

  47. Tell me about a day you chose someone you didn't feel like choosing.

  48. When did you last give something up for people you'll never meet?

  49. What have you made that nobody else has ever seen?

  50. What in your life only makes sense to you looking back?

  51. What do you look forward to in old age?

  52. Who did you lose respect for, and what did it take?

  53. What would someone have to do for you to never forgive them?

  54. Where did your idea of a good person come from?

  55. Who shows up in your dreams that you don't think about awake?

  56. What is the worst thing that could happen if you fail?

  57. When did you first feel poor, or rich, compared to the people around you?

  58. What is the "sacred" rule of friendship?

  59. At the very end, what do you hope is going through your head?

  60. If your life was a book, what would its title be?

How to play Deep

  1. Start the deck and read the first card out loud. Whoever wants to answer goes first, or go around the group.
  2. Swipe left or tap the arrow for the next card, and swipe right to go back. Skip any card that doesn't suit the moment. There are no points.
  3. Follow-up questions count. If an answer is interesting, stay on it before moving to the next card.

Going through every card takes about 25–40 min, but there's no need to finish in one sitting. The deck runs in your browser with nothing to install, and your place is saved on this device, so you can stop and pick it up later.

Further reading

Deep Conversations for Couples: How to Get Past the LogisticsLong relationships drift into talk about bills and schedules. What research on couples says about staying curious, five kinds of questions that help, and how to make it a habit.