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Not everyone processes emotions in the same way. Unless you understand this, you will continue to be an asshole. Okay, maybe he goes on for too long, and that's a problem that he has. However, you telling him that he should stop bitching about it because "it makes things worse" does NOT help. If you're going to react to it, tell him that it makes you feel bad that he goes on about it for so long. That's a more appropriate response, and it MIGHT get through to him.