35 Interesting Questions You Never Thought To Ask Your Sibling But Should

1. What would you change, if anything, about our experience growing up?

2. What do you admire most about Mom and/or Dad?

3. In what ways did Mom or Dad let you down?

4. What’s something you wish you could have told me when we were kids? Why didn’t you tell me then?

5. How could I have been a better sibling to you when we were growing up?

6. What’s your favorite childhood memory of us?

7. What’s the worst fight we’ve ever had?

8. Who was the first person to break your heart?

9. Were you ever bullied? Did you ever bully anyone?

10. What’s my most annoying habit or quality?

11. What memory of us still makes you laugh?

12. Do you think our parents had a favorite kid? If so, who and why?

13. What was your biggest insecurity as a teenager?

14. How did you lose your virginity?

15. What’s your love language?

16. If you had a Saturday with no plans, how would you spend it?

17. What event in your life has had the most significant impact on you?

18. What is your biggest worry these days and why?

19. Where’s a place you wish you could live for a few months?

20. Do you consider yourself successful?

21. What’s your hidden talent?

22. What’s one healthy thing you do to manage stress? And one unhealthy thing?

23. Do you believe in God or a higher power?

24. What’s something you wish more people knew about you?

25. What’s the social or political cause you’re most passionate about?

26. Who would you want to give the eulogy at your funeral?

27. What’s a mean comment someone made about you that’s stuck with you to this day?

28. What’s the most rebellious thing you’ve ever done?

29. When do you feel the most confident?

30. How would you describe your relationship with money?

31. What song or movie scene makes you cry without fail?

32. If salary and experience didn’t matter, what job would you most want to have?

33. If we could go on a dream trip together, where would we go and what would we do there?

34. How do you feel about getting older?

35. What’s something that scares you now that you hope you do before you die?

This article originally appeared on HuffPost.