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Metropolitan

During Manhattan debutante season, middle-class Princeton student Tom Townsend attends a deb ball on a whim. A mix-up over a taxi home introduces him to a small group of young Upper East Side socialites known as the Sally Fowler Rat Pack, after the girl whose fancy apartment they use for afterparties. The Rat Pack invites him to the night's afterparty to prevent ill feelings.

At the afterparty, Tom befriends several Rat Pack members, including Nick, a cynic who takes Tom under his wing; Audrey, a shy girl who enjoys Regency-era literature and develops a crush on Tom; and Charlie, a philosophical friend with an unrequited crush on Audrey. Tom learns that he and the Rat Pack have some common friends, including his ex-girlfriend Serena, with whom he remains infatuated.

Under Nick's tutelage, Tom ingratiates himself with the Rat Pack. Although he initially sticks out due to his left-wing, Fourierist views, he fits into the social crowd and becomes a full-fledged member. Much of the film is composed of dialogues in which the Rat Pack discuss their nebulous social scene and uncertain futures. They worry that they are coming of age just as the culture in which they were raised is ending.

One reason Tom fits in is that his social cachet trumps his wealth. He attended the Pomfret boarding school at the same time that Serena went to Farmington with several Rat Pack girls. Nick explains that the Rat Pack needs Tom because there is a shortage of socially respectable young men to escort debutantes to formal events.

Although the Rat Pack welcomes him, Tom harbors a love–hate relationship with wealth and the upper class. His wealthy father abandoned the family to marry another woman, forcing Tom and his mother to move into a middle-class apartment on the Upper West Side. Tom slowly realizes that he is in denial about his distant relationship with his father.

Serena has been dating Rick Von Sloneker, a young, titled aristocrat notorious for his womanizing. Nick resents Rick and accuses him of getting a girl drunk and convincing her to " pull a train " several years ago, after which she committed suicide. When Rick confronts him, Nick admits that his story is a "composite" of incidents from Rick's life. He insists that it is based on real events, but the Rat Pack is scandalized.

As debutante season ends, the Rat Pack unravels. Nick leaves Manhattan. During a parlor game, Tom admits he loves Serena and not Audrey. In response, Audrey leaves to spend the rest of the vacation with Rick and their mutual friend Cynthia in the Hamptons. Charlie, who tells himself that society is out to get the elite, is surprised to hear that other young elites have achieved success in life. Tom learns that Sally is surreptitiously dating Allen, an older record producer; it is implied that Allen promised to make her a star.

Realizing that he has developed feelings for Audrey, Tom recruits Charlie to help him rescue her from Rick. The two travel to Southampton, bonding en route. They are surprised to find Audrey in no peril. Tom and Charlie instigate a fight with Rick, who asks them to leave. Audrey is delighted to see that Tom and Charlie have come for her, and leaves with them.

Tom and Audrey talk on the beach. Audrey says she is planning to attend college in France, and Tom contemplates visiting her there. Tom, Audrey, and Charlie begin hitchhiking to Manhattan together.