52 Questions To Ask If Youre Ready To Really Get To Know The Deepest Parts Of Someone

Benjamin Davies


1. What is the darkest thought you’ve ever had? What about the darkest thing you’ve never told anybody?

2. Is there something out there, a thought, an idea, a current event, or a fear that you find deeply unsettling?

3. What would you consider to be your deepest fear? (This question can be really telling of the depth or lack thereof of a person.)

4. Is there an activity that calms you? A place or a thing that makes you feel at ease?

5. What makes you feel uneasy? Overwhelmed? Anxious?

6. What is your favorite song and why?

7. Do you have a favorite book? A line in a piece of literature? A poem? Why do you relate to it?

8. What scene in a movie has evoked the most feelings out of you?

9. What do you do or where do you go when you need to be alone?

10. What makes you feel like you need to be alone?

11. Can you remember a time in your life you felt the most alive? Tell me everything about that memory.

12. When have you felt the lowest in your life?

13. Where have you felt the most failure? The most success?

14. Tell me about the facts or harsh truths you choose to ignore but know you shouldn’t.

15. When have you felt like you were living life to the fullest? When have you felt like you weren’t?

16. What is the first lie you ever told? Which is the biggest?

17. What is the first secret you ever kept from anybody? Which is the biggest?

18. Are you a religious or spiritual person? Tell me why and tell me how.

19. Have you always had the same political beliefs? Is there something that impacted them?

20. Where do you find meaning in your life?

21. Have you ever been in love? Tell me about the times you have been.

22. Tell me about the times someone broke your heart.

23. Why did you cry the last time you did so?

24. Have you ever cried tears of joy?

25. What did you do when you hurt someone the most?

26. If your life was a movie or a book what would be the title to it?

27. When have you caused the most harm to yourself?

28. What has been the biggest change you ever made that made you the most proud of yourself?

29. Think about the people you love the most in your life, what do you do for them?

30. Is home for you a place or a feeling? Describe that place or describe that feeling.

31. If you could be anywhere other than where you are right now, where would you be and what would you be looking at?

32. Have you ever questioned your sanity and why?

33. What is your most cherished childhood memory?

34. Have you ever had dreams about a past life?

35. Do you have any recurring dreams or nightmares?


36. Do you believe more in fate or that we are the creators of our own destinies because we are governed by free will?

37. Do you believe in extraterrestrial life? Elaborate on why or why not.

38. Would you find more comfort in the theoretical idea that that we were the most advanced species in outer space or would you find more comfort in the idea that we weren’t?

39. What would be your thought process if you were presented with irrefutable evidence that a god didn’t exist? What would be your thought process if you were presented with irrefutable evidence that a god
did exist?

40. What do you think was there before the universe came into creation?

41. Do you believe in other dimensions and parallel universes?

42. How do you define art?

43. If you could have the option of eradicating pain from your life would you choose to do so? Why or why not?

44. Is a life exclusive to pleasure (no suffering) worthwhile?

45. What do you think happens after death, if anything?

46. If you could be given the date of your death would you want to know it?

47. Presented with the opportunity to be immortal would you take it?

48. Would you rather be loved or love?

49. How do you define beauty?

50. Where does happiness come from? Define what happiness means to you.

51. Do you believe yourself to be truly free? If so, why? If not, what is holding you back?

52. Deja-vu: is there anything to it or merely coincidence?

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