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"He tells his friends he has zero respect for her, that he only hangs out with her because it makes him feel good about himself."

highkey this would be enough for me to break off a friendship

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It reminds me of the ol' "He who despises himself, still esteems himself as a despiser." If he found her unilaterally contemptible, he would probably find her praise disgusting. Breaking off or standing up to him are of course good, but he sounds to me like an ashamed individual playing the male role for his friends. While definitely the more difficult solution, I have found it more helpful to address the hypocrisy than to just break things off.

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"We all start off as amorphous slabs of marble, and we chip away at it to find our “truest form.” This is so beautiful, I love this analogy.

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Speaking of chaos, I once had a friend tell me that they might be interested in more than friendship but would want to stay friends with me regardless. As it turns out, being romantically involved was extremely impractical given our health limitations and the fact that we live on different continents. We initially seemed to be on the same page that it didn’t make sense to pursue, but soon enough my reluctance to engage in romantic behaviors was pathologized as fear and anxiety, making it hard to remain friends.

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