After discovering his high school crush can't date until her brash older sister does, a lovesick teen enlists a bad-boy classmate to woo her.

Heath Ledgeras Patrick Verona
Julia Stilesas Katarina Stratford
Joseph Gordon-Levittas Cameron James
Larisa Oleynikas Bianca Stratford
David Krumholtzas Michael Eckman
Andrew Keeganas Joey Donner
Susan May Prattas Mandella
Gabrielle Unionas Chastity
Larry Milleras Walter Stratford
Daryl Mitchellas Mr. Morgan
Mark Irwin