Conversation Understanding

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I had an interesting conversation with my friend early this morning and I had a realization, our ideas of "Understanding" are very different. She was talking to me about how she felt about various subjects and the way she relates conversations and event between her and other people and would ask me now and again if I understood what she meant. I agreed because I understood what she was saying.

She was speaking English. I know this language too. I know the meaning of the words she was using. Then I realized, about two hours after the fact that maybe she was wondering if I understood the concepts in some deeper way. I realized I am never really going to get that sort of feeling.

One of the things she said was "I can talk to XYZ and he does not ask anything of me, and I don't ask anything of him." I was like, they ask each other rhetorical questions then. Just conversing and I guess she thinks that's nice. And though I understood the explanation she gave me because I am not stupid, I do not understand this ethereal unseen connectedness that this conversations with this person gives her.

Anyone else ever realize this? Or am i just weirder than the norm around here?

I'm not quite sure I understand. Is this about a particular person and her relationship with somebody else? As in, she gets something out of the conversations she has with him because she and the other person have a bond of some sort?

Or is it a question about the concept of "understanding" in general? As in, what each person individually might think they "understand" from a given sentence?

Or is the question you're asking exactly the question I'm asking?...