During the summer of 1999, a group of teenagers, through interconnected narratives, live through their last day of high school and prepare for the future. Holly, once the new girl in school, does whatever it takes to remain popular. Dawn, who is secretly a lesbian, battles drugs. Tori is the valedictorian of her class, but, on the eve of graduation, she decides to experiment with drugs for the first time.

Charlie, a socially inept young man, compulsively confesses every detail of his anti-social behavior to his mother, Hazel, with whom he still lives in Harlem. When his mother asks him to finally move out of her apartment, Charlie is forced to confront his greatest fears - losing his only life witness and living in a world without his only friend and confidante.

Marty, a lovelorn student at New York University, uncomfortably mingles with fellow members of his debate team at a college party, before breaking away from them entirely.