Siblings know you longer than almost anyone. They were there before your first day of school. They saw you ugly-cry at your high school graduation. They know the version of you that existed before the world shaped you.
And yet — how many of us really know our siblings?
Not the surface stuff. Not favorite foods and job titles. The real things. The memories you both lived through but remember differently. The dreams they never told Mom and Dad. The moment they felt most alone — and why.
These 30 interesting questions to ask your siblings are designed to go there. To get past the small talk and into the conversations that actually matter.
Why It’s So Hard to Have Deep Conversations With Your Siblings
Sarah, 34, has three brothers. At every family dinner, they talk sports, complain about traffic, and debate the best pizza place in their city. “We have a great time,” she says. “But last year I realized I had no idea what my middle brother was actually afraid of. Or what he wished our parents had done differently. We’d been talking for thirty years without ever really talking.”
This is common. With friends, we choose to go deep. With siblings, we assume we already know them. We skip the questions.
The fix is simple: start asking.
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Key Takeaways
- Meaningful questions help siblings move beyond surface conversations and build deeper emotional understanding of each other.
- The prompts reveal shared memories, hidden experiences, personal growth, and how family life shaped each sibling differently.
- Recording these conversations, for example in the Meminto Life Book, helps preserve family stories and strengthen long term connection.
How to Use These Questions
You do not need to sit your brother down and announce that you are about to have a Deep Conversation. That is a fast way to get an eye-roll.
Instead, try one question on a long car ride. Bring one up at a holiday dinner. Text a question on a slow Tuesday afternoon.
Start with lighter questions. Build from there. Let the conversation go wherever it wants to go.
30 Interesting Questions to Ask Your Siblings
Childhood Memories
1. What is your earliest memory of us?
You may remember the same event completely differently. That contrast alone is worth an hour of conversation. Marcus, 41, asked his sister this question over lunch. She described a summer road trip he had completely forgotten. He had stored different memories from the same trip. Two people. One childhood. Two entirely different archives.
2. What is a moment from childhood you still think about?
Not the obvious ones. Not the Christmas mornings. The random Wednesday that never left. For Jamie, it was the afternoon his older sister taught him to ride a bike — not because it was dramatic, but because she never once laughed when he fell.
3. Was there a time you felt like the odd one out in our family?
Birth order, personality, interests — siblings often feel invisible in ways they never say out loud. This question gives them permission to say it.
4. What did you think was unfair about how we were raised?
Be ready for honesty. And be ready to hear something that does not match your experience at all.
5. What is the most mischievous thing we did together that our parents still don’t know about?
This one usually gets a laugh. And sometimes a confession that surprises you.
6. What is a memory of us that you hope you never forget?
Simple. Specific. Meaningful. Elena asked her brother this on a drive home from a funeral. He told her about a night they stayed up until 3am watching terrible horror movies when they were teenagers, and how safe he felt just knowing she was there.
Family and Relationships
7. How do you think our parents’ relationship shaped how you see love?
Parents do not just model parenting. They model partnership — for better or worse. Siblings often carry very different lessons from the same household.
8. Which parent do you think you’re most like, and does that bother you?
The second half of the question is the important part.
9. Is there something about our family you’ve only understood as an adult?
Kids process what they can. Adults revisit it with new eyes. Tom, 38, told his sister that he only understood their father’s drinking when he turned 30. “I used to think it was about us,” he said. “Now I know it wasn’t.”
10. What family tradition do you want to keep? What do you want to leave behind?
This question often reveals what your sibling values most. And what wounded them.
11. If you could go back and change one thing about how we treated each other as kids, what would it be?
This takes vulnerability. But siblings who go here often walk away closer.
Dreams and Identity
12. What did you want to be when you were twelve?
Not five — twelve. By twelve, kids start to understand limits. The dreams they have at twelve are closer to the real self.
13. Is there a path you didn’t take that you still wonder about?
The road not traveled. Most people have one. Siblings rarely talk about it. Priya asked her brother this question and learned he had once been accepted to art school and turned it down because he thought their parents would disapprove. He had never told anyone.
14. What does success look like to you now versus five years ago?
People change. The answer at 25 is rarely the same at 40.
15. What are you working toward right now that excites you?
This is not a polite question. Ask it like you mean it. Then actually listen.
16. What’s one thing you’ve always wanted to do but keep putting off?
And then, if you are feeling brave: why?
Hard Questions (Worth Asking)
17. Is there anything you’ve always wanted to say to me but haven’t?
This one requires trust. Build up to it. But when a sibling answers it honestly, the conversation can change your relationship permanently.
18. Was there ever a moment you felt like I let you down?
It takes courage to ask. It takes more courage to hear the answer without getting defensive. Rachel, 45, asked her younger sister this. Her sister quietly said: “When you didn’t come to my first gallery show.” Rachel had forgotten she even missed it. Her sister had carried it for eight years.
19. What’s the hardest thing you’ve been through that you never really talked about?
Siblings share a house. They do not always share their pain. This question opens the door.
20. Is there something about me you’ve been worried about?
Siblings see things partners and friends miss. Sometimes they’ve been waiting for permission to say it.
Hypotheticals and Fun
21. If you could relive one day from our childhood exactly as it was, which would it be?
The answer tells you a lot about what mattered most to them.
22. If we could switch lives for a week, what do you think would surprise you most about mine?
More interesting than it sounds. It reveals how your sibling sees you.
23. If you could give your younger self one piece of advice, what would it be?
Simple. Classic. Still produces answers that stay with you.
24. What’s one thing our family does that you find completely absurd but love anyway?
Every family has these. Naming them out loud is a small joy.
25. If you had to describe me to a stranger using only three words, what would they be?
Ask this. Then brace yourself. It is almost always illuminating.
Looking Forward
26. What do you hope our relationship looks like in ten years?
Not assumed. Chosen. This question reminds siblings that the relationship is something you can actively build.
27. Is there something you want to do together before we’re too old to do it?
One family answered this question and booked a trip to Portugal six months later. They had been “meaning to travel together” for fifteen years.
28. What role do you want to play in each other’s kids’ lives?
For siblings with children, this matters more than it gets discussed.
29. What’s one thing you genuinely admire about me?
People are not great at saying this out loud. Ask it directly. It feels awkward for about five seconds. Then it doesn’t.
30. What do you want us to be to each other?
The biggest question. The most important one. What is this relationship, really? What could it become?
Preserving These Conversations
The problem with great conversations is that they disappear. You remember fragments. You forget the exact words. You lose the story your brother told about the night he felt most alone.
One way to keep these conversations: a Meminto Life Book.
Meminto sends weekly questions — to your sibling, to you, to your whole family. Each answer builds a record. Over time, you get a book of stories that would otherwise be lost. The everyday moments. The big questions. The answers that only exist between siblings who finally started asking.
It is one of the best ways to hold onto the conversations that matter.
Start With One Question
You do not need all thirty. You need one. Ask your sibling one question this week. A real one. Not “how’s work” — something from this list.
See where it goes.
The conversations you’ve been skipping for years are right there, waiting.
