52 Personal Questions To Ask Someone To Get Them To Open Up

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happy couple sitting on the couch

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 you feel close to them, and they feel the same. They would welcome any deep discussion, but opening up doesn't come easy to them.

For closeness to occur between two people, their relationship must include mutual vulnerability. Revealing something potentially embarrassing about yourself endears another person to do the same.

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With all that in mind, we’ve put together a list of personal questions that encourage people to open themselves up to a deeper level of closeness and vulnerability.

52 Personal Questions to Ask To Get Someone To Open Up

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?

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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 your life from birth, where would you want to be born?

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

15. When was 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 you wish to 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?

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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. What would you expect to be on your tombstone if you are buried when you die?

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

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?

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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 forever, if at all?

33. Have you ever given up on a dream?

34. What food would be served if you had to spend a six-hour dinner with your family?

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

36. What’s a mistake you make a lot?

37. When was 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?

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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 did you want to do when you were younger that you didn’t want to do anymore?

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

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