24 Deep Questions To Ask Your Sibling To Get To Know Who They Are At Their Core

The older we get, the harder it can be to maintain a deep connection to our brother or sister. Asking these questions can help keep those ties strong.

Written on Aug 23, 2024

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Sibling relationships are a unique thing. Perhaps second only to our friendships, they're often the people we're closest to in our lives — but they can also be the connections that are the toughest to maintain as we get older.

Whether we start out as the best of buddies or mortal enemies as kids, we typically find our way toward a devoted relationship with our brother or sister as we get older, only to often begin drifting apart as the pressures of marriage, parenting and careers intensify.

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So how can we maintain those brotherly and sisterly ties? Asking the right questions can help, by cutting through all that stands in the way of connection and the noise of our busy lives, giving us moments to truly connect and show ourselves, and reminding us of the shared history that knit us together in the first place.

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Here are 24 questions to ask your sibling to get to know them as a person and deepen your connection:

1. What is your first memory of me?

2. What do we have in common?

3. What are we opposite on?

4. Do you think our parents treated us the same?

5. Who had it the hardest, who had it the easiest?

6. Who did you think was the favorite growing up?

RELATED: 4 Things Standing In The Way of You Becoming Best Friends With Your Siblings

7. Which parent were you closest to and why?

8. Which of our parents am I most like? Why?

9. What’s the one thing you wish we still did?

10. When do you think we were happiest as a family growing up? 

11. What was the scariest time in our household when we were growing up?

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12. What advice from our parents has stuck with you in life?

13. What do you intentionally do differently from how we were raised?

14. What is something you’ve learned from me?

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15. What’s one way I’ve changed for the better?

16. What is one thing that is still the same?

17. What can I do to support you more as a sibling?

18. What do you think we should be doing to support our parents as they age?

19. If you could have changed one thing about our family life growing up, what would you have changed?

20. If you could change one thing about our family now what would it be?

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21. When was the last time you cried?

RELATED: 11 Signs You Grew Up With A Little Brother And Your Life Is (Mostly) Better For It

22. What’s one thing you wish for my future?

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23. What is the last thing I did that upset you?

24. Are you proud of me? If so, why?

It's only natural for our sibling relationships to change as our lives progress, in ways both positive and bittersweet. But if we're lucky, those childhood bonds grow right along with us, weaving in and out of all the ups and downs, beginnings and ends, and enriching the lives of our partners and kids too.

By taking a moment to get back to basics, truly connect, and delve into who our child selves have grown up to be, we can strengthen those lasting links even more, so they endure through every chapter of our shared history.

RELATED: How Your Birth Order Secretly Affects Your Whole Personality, According To Psychology

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John Sundholm is a news and entertainment writer who covers pop culture, social justice and human interest topics.

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