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I've known people like this - they're usually people with some kind of social dysfunction. I.e. they just never grew up enough, or something, but haven't learned how to deal with people in a mature manner. I'd bet his xanga is full of terribly dark and awesomely deep observations and drama about his relationships - lots of girlfriends are 'soul mates', 'no one understands my very deep pain'... it's usually just a lot of immature bollocks.
I would suggest a new roommate and don't even think about him. It's going to be a while before he grows up, or whatever it is that he needs to do. You don't need to be around to get sucked into the melodrama bull. I've seen it a LOT.
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My heart knows me better than I know myself, so I'm gonna let it do all the talkin'.
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