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OP has offered the following explanation for why they think they might be the asshole:
I feel like I might be the asshole because I feel like I misunderstood him
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NTA But family suck to ask as bluntly. A general question would be :"So what's new in your life"
NAH. you are permitted to not agree. However, somethings are annoying to one person, and not another. Your brother does not want to discuss his sex life, and that is perfectly reasonable, he shouldn't have to. And your family should respect that and not hound him on that. So, it is perfectly fine that you are Ok with that type question, but respect your brother and his wish to not be asked about that subject, and try to be supportive. You will find as life goes on, there will be things that annoy you that he doesn't have a problem with, and it is nice to have someone in your corner, even if they themselves do not have a problem with something.
NTA but this is clearly something your brother is sensitive about so you could keep that in mind when choosing how to address the topic in the future.
NAH. The two of you disagree. It’s fine to disagree. Your brother is being hassled by family though, it’s a shame you can’t accept that he feels hassled by the hassling.
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So my(17F) brother(23M) talked to me on how he was annoyed that our cousin(25M) asked him if he has a girlfriend. Which my brother don’t. Then he gets upset about how our extended family keeps asking that. I don’t seem bother that my extended family ask me that. It was just a general question tbh.
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NTA but it is clearly a sensitive topic for your brother. But it is a normal thing to be insecure about, and it probably strikes a cord especially with family asking him again and again.