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I'm trying to find a movie about a geeky guy and girl who figure out how to be cool then start

Having all sorts of one night stands. She like his neighbor and the geeky guy figures out that he loves her but then she starts hooking up with the neighbor. Then she realizes she likes him and they start hooking up. I feel like the girl is Kristen Wiig but couldn't find anything like that with her in it. The girl is really skinny and funny. She turns into a big slut. Please help me figure out what this movie is? At one point in the movie he buys a leather jacket and I think gets in a bar fight.


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