Paul Tannek (Jason Biggs) is a small town scholarship student in the big city having trouble fitting in at his New York college. With his plaid hunter's cap and kind, good-natured personality, Paul is an outsider among the self-anointed, sophisticated hipster crowd. As for his pot-smoking, girl-chasing roommates, Paul's need to study takes a back seat to their overwhelming desire to party. Roommate Chris can only offer a floundering Paul this piece of advice: "For your own good, just try to be not so much like you." To make matters worse, Dora Diamond (MENA SUVARI), the girl of Paul's dreams, only has eyes for their English Lit professor, Edward Alcott (GREG KINNEAR). Dora is down on her luck, too, she's practically broke, has nowhere to live, and her professor boyfriend is more interested in manipulating and controlling her than having a real relationship with her. Things appear pretty bleak for Paul until the college billets him in a local veterinary hospital, where he suddenly finds himself with something everyone else wants (a place to party) and something Dora really needs (a place to stay). Kindred spirits, Paul and Dora grow closer; 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 a loser gets lucky sometimes.