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You have to broach the subject with him. I've been lucky, and all my roommates have been pretty good with mess. I'm usually the messy one.
But you aren't going to get anywhere staying silent and angry. I think that you should inform him of the way the mess annoys you, and about the incident with the girl. Let him know you don't want to ruin your friendship over some damn trash, but that you'd appreciate it if he would clean up and throw his garbage in the trash.
Sometimes just telling the person works wonders.
Good luck!
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