It's two days before graduation, and Jack (Affleck) is having serious doubts about the future. The old gang is breaking up: Rob (Rockwell) is moving to L.A. with his girlfriend; Dennis (Stewart) is finishing his third degree and going to grad school in Michigan; Slosh has dropped out of school and stays drunk all the time; and Mickey, who still has a year of school to go, seems tired of the scene and wishes he had the guts to tell his friend Chelsea (Milano) how he feels about her. As Jack looks out at his four years in Santa Cruz, he wonders if this isn't the best time of his life, and he wonders whether it might be a mistake to let it all go just because of graduation...