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Cameron James, a new student at Padua High School in the Seattle area, falls in love at first sight with beautiful and popular sophomore Bianca Stratford. Geeky Michael Eckman warns him that Bianca is vapid and conceited, and that her overprotective father does not allow Bianca or her older sister, the shrewish Kat, to date. Kat, a senior, is accepted to Sarah Lawrence College in New York, but her father, Walter, wants her to stay close to home. Bianca wishes to date affluent senior Joey Donner, but Walter, an obstetrician worried about teenage pregnancy, will not allow his daughters to date until they graduate. Frustrated by Bianca's insistence and Kat's rebelliousness, Walter declares that Bianca may date only when Kat does, knowing that Kat's anti-social attitude makes this unlikely.

When Cameron asks Bianca out, she informs him of her father's new rule and, as a pretense for allowing her to date Joey, suggests that Cameron find someone willing to date Kat. Cameron selects "bad boy" Patrick Verona, but Patrick scares him off. Michael assists by convincing Joey to pay Patrick to take Kat out, under the pretense that this will allow Joey to date Bianca. Patrick agrees to the deal, but Kat rebuffs his first few advances. Michael and Cameron help him by probing Bianca for information on Kat's likes and dislikes. Armed with this knowledge, Patrick begins to win Kat's interest. She goes to a party with him, which enables Bianca to go as well, much to Walter's dismay.