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If its that big of a hassle to live with him, find another roommate.
I know you 'like' him and all, but I've seen my best friends go through this. It starts off them being roommates, but soon turns into something like this. One becomes a free-loader, always mooching and never chipping in, while the other is the sort of push over that the first one can manipulate. It got bad, like serious fist fight bad, until I had to help one move, yet still be cool with both (awkward).
Hes probably a good friend, but if hes not being a good roommate, and you guys can't work it out, you might just want to get a new roommate, or get your own place or something. Borrowing gloves isn't that big of a deal, but I understand that you wanted to keep your nice gloves nice, and I feel the not lending your skis and boots so some random dude.