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Whether a friend, a family member, a significant other, or a life-long partner, these are good questions to ask if you really want to get vulnerable with someone you love and know who they really are underneath the surface.
1. What’s the scariest thing you’ve ever done?
2. What’s one moment that you wish you rewind and replay 100 times?
3. When its 3am and you’re all alone, what do you think about?
4. What’s one thing about the future that scares you?
5. Do you regret anything?
6. What has been your greatest struggle?
7. What has been your greatest triumph?
8. How would you describe yourself to a stranger?
9. What are three words that define who you are?
10. What’s holding you back from your dreams?
11. What’s one thing you’ve never told anyone about yourself?
12. Have you ever done something you wish you could erase?
13. What do you do when you’re feeling lonely?
14. What’s your vice?
15. Have you ever been in love?
16. Have you ever hurt someone you loved?
17. Have you ever been hurt in love?
18. If you could tell your younger self some advice, what would it be?
19. How has your family shaped you?
20. If you could only bring three things with you into your next life/Heaven/after life/etc. what would you bring?
21. If you could only talk to one person for the rest of your life, who would he/she be?
22. What’s something you strongly dislike/hate?
23. What do you think the word ‘love’ means?
24. What do you believe?
25. What is one thing you’ve had to forgive yourself for?
26. If you could relive your life again, what’s something you would change?
27. If you could relive your life again, what’s something you would keep the same?
28. What kind of music do you listen to when you’re sad?
29. If you had to describe yourself in one word, what would it be?
30. What is something you like about yourself?
31. What is something about yourself you wish you could change?
32. What makes you a good person?
33. What is something you’re insecure about, or like to hide from the world?
34. Have you ever had your heart broken?
35. What’s the stupidest thing you’ve ever done?
36. What’s the best thing that’s ever happened to you?
37. What does it mean to truly love someone?
Marisa Donnelly is a poet and author of the book, Somewhere on a Highway, available here.