All Catholic schoolgirl Mary Katherine Gallagher (MOLLY SHANNON) wants in life is a Hollywood style kiss, preferably from school heartthrob Sky Corrigan (WILL FERRELL), the best looking and most popular boy at St. Monica's high school. The only problem is, she's something of a nerdy social reject and besides, Sky already has a girlfriend, Evian (ELAINE HENDRIX), the prettiest and most popular girl at their school who can't stand Mary.
Even so, that doesn't stop her from practicing her make out sessions with inanimate objects such as trees. That behavior eventually gets her sent to the school's special ed. class, taught by Father Ritley (MARK McKINNEY) where she meets other students such as the tomboyish Helen (EMMY LAYBOURNE) and Slater (HARLAND WILLIAMS), a silent and mysterious tough guy who seems attracted to Mary.
Mary's big break comes when she hears that the grand prize for her school's "Let's Fight V.D." talent contest is a trip to Hollywood to appear as an extra in a film with positive moral values. Believing that the only way to get her Hollywood kiss is to become a Hollywood superstar, Mary desperately wants to enter, but her grandmother (GLYNIS JOHNS) who's raising her, adamantly refuses.
Nonetheless and despite Evian's attempts to interfere, Mary perseveres, and with some urging from Helen, Slater and even God (WILL FERRELL), enters the competition determined to win the contest and get her kiss from Sky.