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In the story, new student Cameron (Gordon-Levitt) is smitten with Bianca (Oleynik) and, in order to get around her father's strict rules on dating, attempts to get bad boy Patrick (Ledger) to date Bianca's ill-tempered sister, Kat (Stiles).
The film is titled after a poem written by Kat about her bittersweet romance with Patrick.
Kat confesses to Bianca that she dated Joey when they were freshmen and, succumbing to peer pressure, had sex with him.
Afterward she regretted it and Joey dumped her, so she vowed to never again do anything just because everyone else was doing it.
At the party, Kat becomes upset when she sees Bianca with Joey, and responds by getting drunk.
Patrick attends to her, and Kat starts to open up, expressing her interest in starting a band.
Cameron admits his feelings for her and his frustration with how she has treated him. Joey offers to pay Patrick to take Kat to the prom so he can take Bianca.Patrick surprises her with a guitar bought with the money that Joey paid him, and confesses that he has fallen for her.Kat forgives him, and the two reconcile with a kiss.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 worrisome of teenage pregnancy, will not allow his daughters to date until they graduate.