Paul Tannek (Jason Biggs), a small-town, intelligent kid from the Midwest is accepted into New York University on an academic scholarship. Trying to follow the advice of his father (Dan Aykroyd) he tries to gain friends by trying to be polite and interested in others. His attempts are noticed by his new roommates Chris (Thomas Sadoski), Adam (Zak Orth) and Noah (Jimmi Simpson), three rich, spoiled, obnoxious city boys who consider his polite behavior, working class background and determination for education lame and brand him a loser. To salvage their reputation, the trio concoct a false story to the housing administration about Paul’s attitude and have him thrown out of the dorm. Paul takes residence in a veterinary hospital. Chris meets Paul and again concocts another story about how they were trying to help him as a ploy for Paul to let them use the hospital to throw parties, after an incident where a resident at the dorm fell sick with alcohol poisoning forbid them from holding any parties thereon.
Paul meets classmate Dora Diamond (Mena Suvari) and develops an attraction to her, unaware that she is having an affair with their decorated but highly pretentious English professor Edward Alcott (Greg Kinnear). Dora is equally as intelligent as Paul but doesn’t have a scholarship and works shifts as a waitress in a strip club to pay for her tuition until she is unceremoniously fired. To avoid a long daily commute which she can no longer afford, Dora asks Alcott to let her live with him for a while to which he selfishly declines for fear of losing his tenure at the university if their relationship is found out. Paul and Dora bump into each other one night and Paul invites her to an Everclear concert after discovering when they met that she is a fan. Dora agrees to the date, but first goes to a job interview for a night shift in a convenience store, but is denied the position because she’s a woman. Adam is at the same store buying beer and pretends to be sympathetic as a ploy to invite her to a party which she accepts, but says she will be there only for a short time so she can meet Paul. At the party, one of the boys slips a roofie into Dora’s drink and she passes out. Paul returns dejected from the concert to a huge mess and an unresponsive Dora and immediately rushes her to the hospital. At the hospital, Paul pretends to be her boyfriend since neither he or Dora can afford to keep her there overnight. He also learns that Dora listed Alcott as her case of emergency contact which he tells Chris the next morning without thinking. Alcott tells emergency officials he doesn’t really know her when they contact him.
Paul bonds with Dora as she recovers and they start to develop feelings for one another; he also learns that Dora cannot see past her blind infatuation with Alcott even when she says even though he loves her, he doesn’t want a relationship. While Paul continues with his studies, Dora searches for a new job. She pulls Paul out of class and invites him out to celebrate receiving a spot in a medical experiment. They steal a loaf of bread from a bakery, coffee from a dispenser in the park and sneak into a Broadway show. Paul goes out to grab a pizza and a movie for both of them hoping it may lead to something further between them only to return to find Alcott with Dora and learning that Alcott has changed his mind about Dora living with him. Alcott reveals to Dora that Chris, Noah and Adam are blackmailing him with the knowledge of their relationship in return for a passing grade on their transcript and also tells her that he believes Paul is in on it. After discovering roofies were involved at the party, Paul steals Noah’s supply and replaces them with placebos. Paul then pays a visit to Alcott’s office to ask how Dora is doing and is instead given his final exam as a take-home test by Alcott to buy his silence, Paul takes the moral high ground and refuses the test, jeopardizing his scholarship and place in the university.
Dora, since living with Alcott, has become his errand-girl and overhears Paul on the phone with his father talking about how much he misses her. Alcott then admits he learned that Paul had nothing to do with the blackmail, but still intends to fail him. Dora then realizes that Paul is the one who really loves her and terminates her affair with Alcott, beginning a relationship with Paul. Afterwards, Adam, Noah, and Chris’ behavior get the better of them and their lives plummet into failure, Alcott is found out and sent to prison for having an affair with a different student who is underage, and Paul and Dora remain happy in their relationship.