Sensitive artist-wannabe and social misfit Keith (Stoltz) goes all out to win the heart of the school's most popular girl Amanda (Thompson), though his chances do not look bright. He enlists the help of his best pal, tomboy and fellow misfit Watts (Masterson), who hides her true feelings for him to help him win Amanda’s heart. When he finally succeeds, he realizes that the person he truly loves is someone much closer to him.