Cameron James (Joseph Gordon-Levitt), the new kid at Padua High School, is given a tour of the school by Michael Eckman (David Krumholtz), who is an audio-visual geek and former leader of a clique of future MBAs. Michael provides Cameron with information on the schools various cliques. During the tour, Cameron spots the beautiful and popular Bianca Stratford (Larisa Oleynik) and is immediately smitten with her. Michael warns that Bianca is shallow, conceited, and worst of all, not allowed to date. Michael does, however, inform Cameron that Bianca is looking for a French tutor.
At the Stratford residence, Biancas outcast older sister Kat (Julia Stiles) receives a letter of acceptance to Sarah Lawrence College. Her protective father, Walter (Larry Miller), is distraught by the news, as he wants Kat to attend college nearby. Kat distracts her father by revealing that Bianca was given a ride home from school by Joey Donner (Andrew Keegan). Bianca begs her father to allow her to date, but to no avail. Kat's aversion to dating prompts the father to come up with a new rule: Bianca can only date if Kat is dating.
Cameron starts tutoring Bianca, and she informs him of her fathers rule after Cameron makes many failed attempts to ask her out. This news motivates Cameron and Michael to set out to find a boy who is willing to date Kat.
Cameron suggests Patrick Verona (Heath Ledger), an outcast who is just as ill-tempered as Kat. Cameron tries asking Patrick for his assistance, but Patrick scares him off. Michael then poses the idea to Joey, also attempting to date Bianca, to pay Patrick to take Kat out. Patrick agrees, but Kat, however, wants nothing to do with Patrick. Cameron and Michael finally explain their situation to Patrick and inform him that Bogie Lowenstein (Kyle Cease) is throwing a party (this is actually a plot by Michael to get revenge, as a rumor from Bogie had got him kicked out of their clique). Cameron and Michael spread rumors around school that Bogie&ap