The movie starts out at an American high school with a new student named Cameron sitting in the office of the Principal Ms. Perky. He is then shown around the school by Michael, who will become his best friend. During his tour is when Cameron first sees Bianca Stratford and he instantly falls in love, there is only one problem: she isn't allowed to date. And neither is her sister, Katarina, a senior who loves indie rock and is a feminist. But Kat and Bianca's father alters his house rule, now; Bianca can date... as long as Kat has a date, too. Now, in order for Cameron to date Bianca, he has to find someone to date Kat. So Michael helps him enlist the help of Antagonist Joey, tricking him into thinking that he will get to take Bianca out if he pays someone to take out Kat. Cameron and Michael select Patrick a so-called bad-boy who apparently has been to jail and ate a raw duck. Joey pays Patrick and then after a bit of persistence from Patrick, Kat goes out with him so now Bianca can date also. The two girls go to a party although Bianca has two dates.
At the party Kat gets drunk and throws herself at Patrick, but he rejects her 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. Kat starts table dancing after getting drunk and hits her head on the chandelier, collapsing off the table and into the arms of Patrick who takes her outside. They talk on the swings; however after throwing up on his shoes, Patrick takes Kat home. She unsuccessfully attempts to kiss him after he drives her home, then slams the car door in his face and storms off. Cameron admits his feelings for Bianca, and they kiss in the front seat of his car. The next day, Patrick attempts at apologising but fails, but eventually wins Kat over with a performance of a song over the loudspeaker in front of her entire soccer team.