52 Personal Questions To Ask Someone To Help Them Open Up

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52 Personal Questions To Ask Someone To Help Them Open Up
Self

We all have that one person in our orbit that’s like a moon — they keep their distance and only reflect what’s shown to them.

They rarely, if ever, really talk about themselves. But on a certain level you know they’re your friend and they feel the same. They would welcome any deep discussion, but opening up doesn't come easy to them. 

A New York Times article notes that for closeness to occur between two people, their relationship must be grounded in mutual vulnerability. Revealing something potentially embarrassing about yourself endears another person to do the same.

RELATED: 50 Deep Questions To Ask Your Best Friend (To Get To Know Her Better)

With all that in mind, we’ve put together a list of personal questions that encourage closeness and mutual vulnerability. 

1. If money was no object, where in the world would you live?

2. If you could gain any talent or ability without any effort, what would it be?

3. What’s the most common misconception people make about you?

4. If you were going to be thrown out of your home, what one item would you take with you?

5. What’s a regular stressor of yours?

6. Is there something that used to make you happy but doesn’t anymore?

7. What do you think about before you go to bed?

8. Would you rather have a clear mind or a strong body as you age?

9. If you could magically learn any language in the world, what would it be?

10. Does the thought of death scare you?

11. What’s one change you would make to the world with a snap of a finger?

12. Is there something you would never joke about?

13. If you had to restart life from birth, where would you want to be born?

14. If you had to restart life from now, where would you want to live?

15. When’s the last time you cried by yourself? Is that more or less recent than the last time you cried in front of another person?

16. Do you have a hobby or activity that you wish you could do more with someone else?

17. Are you more afraid of hatred or apathy?

18. Who’s the best person living in your memories?

19. Who’s the worst person living in your memories?

20. Do you have a favorite memory associated with your parents?

21. What’s something you’ve been afraid of for as long as you can remember?

22. What are you most proud of in life?

23. If you are buried when you die, what would you want on your tombstone?

24. If you are buried when you die, what would you expect to be on your tombstone?

25. If you could take a test and find out at which age you were destined to die, would you take that test?

RELATED: 50 Deep Questions To Ask Your Mom (To Get To Know Her Better)

26. Would you want to know what disease or condition you’ll die from decades before it happens?

27. Stepping into your parents’ shoes, what one thing would you have changed about your childhood?

28. When did you realize your parents weren’t perfect?

29. What’s your go-to activity to relax?

30. Do you have dreams for anyone else in your life?

31. If you could choose between fulfilling a wish for yourself or guessing what wishes five family members would want to be granted to them, what option would you pick?

32. Is there a year you wish your life would halt in forever, if at all?

33. Have you ever given up on a dream?

34. If you had to spend a six-hour dinner with your family, what food would be served?

35. What’s something you’ve given up on?

36. What’s a mistake you make a lot?

37. When’s the last time you felt angry at yourself?

38. Have you ever shared a dream with someone?

39. What’s one thing you’d never want to live without?

40. What’s a good memory you have of an ended friendship or relationship?

41. Where do you like to go to think?

42. What’s the best gift you’ve ever received?

43. What’s the best gift you’ve ever given?

44. What’s the worst gift you’ve ever received?

45. What’s the worst gift you’ve ever given?

46. When you apologize, do you focus on acknowledging fault for your actions or explaining why you did it?

47. What do you like to hear in apologies?

48. Would you rather spend 10 years married to someone you loved or 50 years married to someone you liked?

49. What’s a regret you wouldn’t want to have when you’re older?

50. What’s something you could regret, but don’t?

51. What’s something you wanted to do when you were younger that you don’t want to do anymore?

52. What’s something you hope you’ve done a year from now?

RELATED: 100 Deep Relationship Questions To Ask Your Fiancé Before Getting Married

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Matthew Ameduri is a writer who covers astrology, pop culture, and relationship topics.