deep questions for your friends

how to play it in your group chat

• post one question and answer it yourself first. it makes it easier for everyone else.
• one question a night is plenty. these land better slow.
• reply to the answers, not just the question. that is where the good stuff is.

45 deep questions

1. What's something you're currently trying to figure out?
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2. What's an experience that changed how you see people?
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3. What's the last thing that genuinely surprised you?
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4. What's the last thing you changed your mind about?
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5. What's a moment where your friendships with this group really clicked, a moment that made you think how grateful you were for them?
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6. What's a decision you made that seemed small at the time but turned out big?
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7. What's a place you've been that still feels unreal to think about?
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8. What's a song that perfectly scores a specific part of your life?
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9. What's a compliment you've been given that you still think about?
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10. What's something about you that's harder to explain than it sounds?
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11. What's one thing you genuinely look forward to every week?
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12. What's something you've quietly been proud of this year?
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13. What's a feature you'd add to your own brain if you could?
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14. What's a word or phrase that you've been overusing lately?
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15. What's something you wish you'd done sooner?
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16. What's the most unexpected thing you've gotten into recently?
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17. What's your vision of a "perfect day"?
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18. What's an opinion you'll defend forever?
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19. What's a thing from childhood that still shapes how you are today?
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20. What's something you used to be embarrassed about that you're fine with now?
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21. What's something you've learned about yourself from how you act around other people?
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22. What's a question you think about more than you probably should?
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23. What would your perfect birthday look like?
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24. Describe your perfect Saturday in one sentence.
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25. What's a childhood toy or game you still think about?
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26. What's a hobby you want to try but haven't yet?
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27. What's a phrase or saying from your family or friends that stuck with you?
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28. What's something you've gotten way better at because you had no choice?
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29. What's a piece of art, song, or film that hit you harder than you expected?
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30. What's a thing you'd happily do every single day?
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31. What's the best piece of advice you've actually followed?
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32. What's a tradition you want to keep for the rest of your life?
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33. What's something you'd tell your 12-year-old self?
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34. What's a place you visited once and want to go back to?
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35. What's a topic you could talk about forever?
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36. What's something you thought you'd hate but ended up loving?
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37. What's one thing about yourself that surprised you this year?
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38. What's a skill you picked up from a really unexpected source?
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39. If you had to teach a class on one thing, what would it be?
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40. What's a talent you wish you had?
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41. What's one rule you actually live by?
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42. What's the wallpaper on your phone right now?
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43. What's the most ambitious thing on your bucket list?
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44. What's a memory from last summer?
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45. What would the title of your memoir be?
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