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two nerds fall in love after a string of one night stands

A guy and a girl  who are both nerds figure out how to be cool and 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 his 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.
asked Dec 18, 2016 in Name That Movie by Tvbean (1 point)
Anything else come to mind? Not teenagers, right? Is this a newer post 2k movie?
Thanks, yes it is newer and they are close to 30. There is a scene where she gets super drunk. They are trying to act younger. Oh and the guy ends up decking out his apartment and the chick gets pissed because it's not like him. I saw it on Netflix just this past year and I am not sure if it's a Netflix original. I feel like I also remember that he has a couple nerdy friends that come to his apartment. Thanks for any help!
This sounds a lot like the Hello Ladies finale. Is that it?
Thanks so much! But that's not it :( it does sound a lot like that one tho!