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

You and your siblings may have grown up in the same house and shared the same parent or parents, but that doesn’t mean you experienced those first chapters of life in the same way.

Maybe you were close when you were little but drifted apart as you got older; maybe you were sworn enemies when you were kids but now you’re tighter than ever — or somewhere in between. Regardless of how well you think you know each other, there’s a good chance you’ve only begun to scratch the surface.

We’ve compiled 35 conversation-starting questions — along with help from psychologists Rebecca Leslie and Erlanger Turner and therapist Nicole O-Pries — that can help deepen the bond you share with your siblings.

Ask your brother or sister some of these during your next phone call or family visit. You might be surprised by their answers.

These questions may help you and your sibling connect on a deeper level. 

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?

Blissed Connections is an editorial series that explores practical ways to strengthen and deepen the relationships you have — or want to have — with the people in your life.