On the first day at his new school, Cameron (Joseph Gordon-Levitt) instantly falls for Bianca (Larisa Oleynik), the gorgeous girl of his dreams. The only problem is that Bianca is forbidden to date...until her ill-tempered, completely un-datable older sister Kat (Julia Stiles) goes out, too. In an attempt to solve his problem, Cameron singles out the only guy who could possibly be a match for Kat: a mysterious bad boy (Heath Ledger) with a nasty reputation of his own!