Loser (2000)

Nerdy, good-natured Paul Tannek is a square peg in a round hole that is New York University- his pot-smoking, girl-chasing roommates hate him, and everyone else on campus ignores him. But when he meets fellow student Dora Diamond, he discovers a kindred spirit. Dora is practically broke, has nowhere to live, and her boyfirend, Professor Edward Alcott, is more interested in manipulating her than loving her. The more people push them around, the closer Paul and Dora get- she helps him dress better and appreciate New York, he lets her stay with him while she finds a job. In the end, Paul and Dora not only fall for each other, they find the courage to walk away from the people who walk all over them- proof that even losers get lucky sometimes.