This movie is a modernization version of Shakespeare's The Taming of the Shrew. The movie is titled after a poem written by the film's leading lady Julia Stiles to describe her bittersweet romance with the male lead Ledger. The film was released back on March 31, 1999, and it was a breakout success for stars Stiles and Ledger.
Cameron James (Gordon-Levitt), a new student at Padua Stadium High School, is given a tour of the school by Michael Eckman (Krumholtz), an A.V. geek. During the tour, Cameron notices the beautiful and popular Bianca Stratford (Oleynik) and he is immediately smitten with her. Michael warns Cameron that Bianca is shallow and conceited, and that her father does not allow her to date. However, Michael does inform Cameron that Bianca is looking for a French tutor.
At the Stratford residence, Bianca's outcast older sister, Kat (Stiles), is in conflict with their overprotective father (Miller), who wants Kat to attend college nearby despite her acceptance to Sarah Lawrence College. Bianca is also fighting with their father regarding his strict no-dating rule. Kat's aversion to dating prompts their father to come up with a new rule, to Bianca's fury: Bianca can only date if Kat is also dating.
Cameron starts tutoring Bianca (despite knowing little French himself). After Cameron makes a failed attempt to ask her out on a date, she informs him of her father’s rule. This motivates Cameron and Michael to find a boy who is willing to date Kat.
Cameron suggests Patrick Verona (Ledger), another outcast who is just as ill-tempered as Kat. Cameron tries asking Patrick for his assistance, but Patrick scares him off. Michael suggests that Joey Donner (Keegan), an affluent student and model who also wants to date Bianca, pay Patrick to take Kat out. Patrick agrees, but Kat wants nothing to do with him. After a little effort, Patrick gets Kat to attend a party with him, but rejects her advances, leaving her angered and unwilling to talk to him. At the party, Bianca sees Cameron but is dragged away by Joey. He poses and tries to please her when Bianca realizes he is just obsessed with himself. The next day, Patrick eventually wins Kat over with a performance of "Can't Take My Eyes Off You" in front of her entire soccer team. They become a couple, but Kat remains unaware that Patrick was paid to date her. Meanwhile, Cameron continues to pursue Bianca, but she remains interested in Joey, unaware that he plans to use her only for sex.
Bianca tries to convince her father to let her attend the prom with Joey, but he refuses because Kat is not going to the prom. When Bianca confronts Kat, it is revealed that Kat previously dated Joey and they slept together once since "everyone was doing it". She tells Bianca that her feelings of isolation from her fellow students dated from that incident and that she would never again do anything just because it was the popular thing to do.
Bianca and Kat end up going to the prom with Cameron and Patrick, respectively. Joey is furious to learn that Bianca has gone to the prom with Cameron, and confronts Patrick about the "arrangement" in front of Kat. Kat is very angry at Patrick when she discovers the truth and she leaves him at the prom. Joey subsequently confronts Cameron about manipulating the "deal" for himself and knocks him to the floor, but Bianca punches Joey numerous times for using her, for hurting Kat's feelings, and for punching Cameron. Bianca and Cameron share a kiss and leave Joey lying on the floor in pain.
The next morning, Kat and Bianca's relationship appears to have improved drastically as Bianca attempts to comfort her older sister. Their father allows Kat to go to Sarah Lawrence College; she is extremely grateful and hugs him with happiness. Later at school, Kat reads a poem which she wrote for English class, titled "I Hate", revealing her true feelings for Patrick. He is shown to be touched by her revelation. After school, Kat finds a guitar in her car that Patrick bought her with the money that Joey paid him, and he admits that he messed up his and Joey's deal by falling for her. Kat forgives Patrick and the two reconcile with a kiss.
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