How Well Do You Know Me 38 Personal Questions to Deepen Connections

  1. What are your passions or hobbies?
  2. Can you tell me about a memorable childhood experience?
  3. What motivates you in life?
  4. What is your biggest fear?
  5. Describe your dream vacation.
  6. What’s the most courageous thing you’ve ever done?
  7. What’s your favorite book or movie, and why?
  8. What’s a goal you’re currently working towards?
  9. What do you value most in a friendship?
  10. Tell me about your favorite childhood memory.
  11. What’s something you’ve always wanted to learn?
  12. What’s the best advice you’ve ever received?
  13. How do you handle stress or difficult situations?
  14. What’s your proudest accomplishment?
  15. What’s your favorite way to spend a weekend?
  16. What’s something you’re passionate about advocating for?
  17. Describe a moment that changed your life.
  18. What’s your idea of a perfect day?
  19. What’s a talent or skill you wish you had?
  20. Tell me about your family and upbringing.
  21. What’s something that always makes you smile?
  22. What’s the most spontaneous thing you’ve ever done?
  23. What’s your favorite type of music, and why?
  24. What’s your philosophy on life?
  25. What’s the best trip you’ve ever taken?
  26. What’s something you’re grateful for today?
  27. Describe a challenge you’ve overcome.
  28. What’s your favorite food or cuisine?
  29. What’s a dream you’ve yet to fulfill?
  30. What’s your favorite season, and why?
  31. What’s something you wish more people knew about you?
  32. What’s your idea of true happiness?
  33. What’s a habit you’d like to break or build?
  34. What’s your favorite childhood game or activity?
  35. What’s the most meaningful gift you’ve ever received?
  36. What’s something you’ve always wanted to try but haven’t?
  37. What’s your favorite quote or motto?
  38. What’s a place you’ve always wanted to visit?

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