Questions to Ask Your Brother About Yourself
Questions for asking a brother how he actually sees you: what you were like as a child, what he has watched you repeat, and what he has never said out loud.
The questions
Open any question for the note
What was I like as a kid, before I can really remember?
Why ask it
If he is older he holds a few years of your life you have no access to, and if he is younger he watched you from an angle no adult had. Ask for a scene rather than adjectives, because the scene is the part you cannot reconstruct yourself.
What's the first thing you think of when someone asks what I'm like?
Why ask it
This is the version of you that circulates when you are not in the room. It is usually one trait plus one story, and hearing which story he picked is often the surprise.
What did you think of me when we were teenagers?
Why ask it
Siblings rarely revise their teenage read of each other unless asked to. If his answer sounds like a description of a stranger, that is worth following, because it may still be shaping how he treats you.
What do I do well that I don't seem to know about?
Why ask it
The interesting answers are the unglamorous ones: you remember birthdays, you are the one people call. Ask him for something you have never been complimented on, or you will just get your resume back.
How do you think our parents treated me differently from you?
Why ask it
You each got a different set of parents in practice, and neither of you can see your own version clearly. Expect to disagree, and resist correcting him while he answers.
When have you seen me at my best?
Why ask it
Notice whether he reaches for an achievement or a moment you barely registered. Brothers tend to remember the second kind, which is why the answer is worth more than praise from a friend.
Have I changed in the last few years? How?
Why ask it
People who see you occasionally track change better than people who see you daily. If he says you have not changed at all, ask what he would expect to see if you had.
Where do you think I sell myself short?
Why ask it
He has watched you turn things down. The specifics of what you avoid, jobs, arguments, invitations, are easier to see from the outside than the reason you avoid them.
Is there something I believe about myself that you think isn't true?
Why ask it
This asks him to contradict your self-description, which most people will only do if you make it clear you can take it. Sit with the answer instead of debating it in the moment.
What do you think I'm afraid of?
Why ask it
Fear is easier to spot in someone else's behavior than in your own reasoning. He may name something you have always described as a preference rather than a fear.
Is there something I do that annoys you that you've never said?
Why ask it
Ask this only if you will not argue. The value is in the small recurring things, interrupting, being late, telling a story about him in front of others, which are exactly the things people never raise.
What do you notice about how I am with the people I date?
Why ask it
Family sees the pattern across partners rather than the current relationship. If several people you have brought home get described the same way, that is information you cannot get anywhere else.
When things go badly for me, what do you see me do?
Why ask it
You know how it feels from the inside; he knows what it looks like from the outside, which is usually going quiet, getting busy, or getting sharp with whoever is nearest.
Is there something you've watched me repeat that you wish I'd stop?
Why ask it
This is the question most likely to produce something genuinely new, because it needs a longer view than a friend has. It also tends to be the one he has been waiting to be asked.
Have I ever let you down?
Why ask it
Expect either a fast no or a specific date, and treat a fast no with suspicion. The point is to hear it once without defending yourself, which is harder than it sounds.
When did I come through for you?
Why ask it
Worth asking straight after the previous question so the conversation does not end on the debt. His answer often reveals a moment you thought was minor at the time.
What do you think I actually want out of my life?
Why ask it
Compare his answer with what you would have said. A large gap usually means you have been telling him about your plans rather than your reasons.
Do you think I'm happy?
Why ask it
He is answering from evidence he has not sorted through, so the hesitation before the answer carries as much as the answer. Ask what he is basing it on.
What do you wish I understood about you?
Why ask it
Turns the conversation around before he starts to feel used as a mirror. It also often explains an answer he gave earlier, because how he reads you depends on what he thinks you have missed about him.
Is there anything about us growing up that you've never told me?
Why ask it
Leave a long silence after this one. Siblings usually hold at least one thing back, and it tends to come out only when the question is open rather than specific.
How to ask, and how to hear the answers
Practical guidance for the conversation itself
Setting it up
Say why you are asking
A brother who is asked out of nowhere what he thinks of you will assume something is wrong, or that he is being set up. One sentence fixes it: you are curious how you come across to someone who has known you the whole time.
Pick a side-by-side setting
Driving, walking, cooking, fishing. Sitting face to face across a table raises the stakes for exactly the questions that need low stakes. Brothers who never talk like this find it easier when their hands are busy.
Take three questions, not the list
Pick the three you would actually be uncomfortable hearing answered, and ask those. Working through twenty in order turns it into an exercise and he will start giving you the polite version.
Offer to answer the same one back
Every question here works in both directions. Answering it about him first makes the whole thing an exchange rather than an evaluation, and it shows him the level of honesty you can handle.
When the answer stings
Say thank you, then stop
The instinct is to explain the context he missed. Do not, at least not that day. If you correct the first honest answer, you will get careful ones for the rest of the conversation.
Ask for the evidence, not the verdict
'What did you see that made you think that?' turns a judgment into something you can check. It also protects you from taking a throwaway remark as a considered view.
Expect his facts to differ from yours
Shared childhood memories diverge more than people expect, and the two accounts are rarely reconcilable. Treating his version as his experience rather than a claim about yours keeps the conversation alive.
Look for what repeats
One uncomfortable observation is his opinion. The same observation from your brother, a partner and a colleague is a pattern, and that is when it is worth doing something about.
What tends to go wrong
Fishing for reassurance
If what you want is to hear that you are doing fine, he will sense it and supply it, and you will learn nothing. Ask the reassurance question directly instead and let the rest be honest.
Turning it into an old argument
Questions about your parents and your childhood sit next to grievances that already have a well-worn script. If you feel the script starting, name it and move to a different question.
Asking during a family event
Holidays put an audience and a time limit on it. Both of you will perform for whoever is in the next room, and neither of you will say the thing worth saying.