Sophomore Al Connelly (Freddie Prinze Jr.) meets the girl of his dreams, freshman Imogen (Julia Stiles), and true love abounds. The two engage on a whirlwind courtship--they pick a song, eat a cake together, even make love. But Imogen's fear of lost youth causes her to push away from Al, and they go their separate ways. Al attempts to rebound from the relationship, determined to forget Imogen, and he goes to desperate measures to do so. The story is told from the points of view of both Al and Imogen.