Nick Pearson hatte sein Leben lang Angst vor Bindungen und hat somit die meiste Zeit als Single verbracht. Nun ist jedoch endlich der Zeitpunkt gekommen, an dem er bereit ist, sich niederzulassen und eine Familie zu gründen. Ausgerechnet am Tag seiner Hochzeit steht jedoch ein 13-jähriger Junge vor seiner Tür, der behauptet, sein Sohn zu sein und ihn dank der Hilfe eines Mediums gefunden zu haben. Am liebsten würde Nick den Jungen sofort wieder zu seiner Mutter schicken. Das Problem ist bloß, dass er keine Ahnung hat, wer das sein könnte. So bleibt ihm nichts anderes übrig, als sich auf den ungebetenen Gast einzulassen und einen Road Trip zu unternehmen, der Nick mit einem unangenehmen Kapitel aus seiner Vergangenheit konfrontiert.
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Cameron James, a new student at Padua High School in the Seattle area, becomes smitten with beautiful and popular sophomore Bianca Stratford. Geeky Michael Eckman warns him that she is vapid and conceited, and that her overprotective single father Walter, an obstetrician worried about teenage pregnancy, has forbidden her or her shrewish older sister Kat, a senior, 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 unsocial attitude will complicate it. When Cameron asks Bianca out, she informs him of her father's new rule and suggests he find someone willing to date Kat; unbeknownst to Cameron, Bianca wants to date affluent senior Joey Donner. Cameron selects Australian "bad boy" Patrick Verona. Michael convinces Joey to pay Patrick to ask out Kat. Patrick agrees, but Kat rebuffs his first few advances. After Michael and Cameron probe Bianca for information on Kat's preferences, Patrick begins to win Kat's interest. She goes to a party with him, enabling Bianca and her best friend Chastity Church to tag along. At the party, Kat becomes upset upon seeing Bianca with Joey, and responds by getting drunk. Patrick attends to her, and she starts to open up to him, expressing her interest in forming a band. When Kat attempts to kiss him, Patrick pulls away, causing her to depart, infuriated and embarrassed. Meanwhile, Bianca upsets Cameron by ignoring him for Joey, but she realizes that Joey is shallow and self-absorbed. When she asks Cameron to drive her home, he calls her selfish for the way she treated him and says his feelings for her are true; she kisses him in response. Joey pays Patrick more money to take Kat to the prom so he can take Bianca. Although Kat is still angry with Patrick, he wins her over by serenading her with a performance of "Can't Take My Eyes Off You" by Frankie Valli, and she returns the favor by helping him sneak out of detention. Their subsequent date turns romantic and they kiss, but Kat becomes suspicious when Patrick insists she accompany him to the prom, which she adamantly opposes. Irritated that Cameron has delayed asking her to the prom, Bianca accepts Joey's invitation, but Walter declines to allow it unless Kat accompanies her. Kat confesses to Bianca that she dated Joey when they were freshmen and, succumbing to peer pressure, had sex with him once and regretted it. After Joey dumped her, she vowed against doing things out of peer pressure, and stays unsocial to protect Bianca. Bianca insists that she should be able to have her own experiences, and Kat decides to go to the prom with Patrick. This lets Bianca go as well, and she attends the prom with Cameron instead of Joey. At the prom, Bianca learns from Chastity that Joey was planning to have sex with Bianca that night. Angry that Bianca spurned him for Cameron, Joey confronts Patrick, revealing that he had paid Patrick to date Kat and leaving her heartbroken. Joey punches Cameron, but Bianca punches and beats him for hurting her, Kat, and Cameron. The following day, Bianca reconciles with Kat, and is now officially dating Cameron. For an assignment in which the students were tasked to write their own versions of William Shakespeare's Sonnet 141, Kat reads aloud her version, entitled "10 Things I Hate About You", revealing that she still cares for Patrick. He surprises her with a Fender Stratocaster that he bought with the money Joey paid him, and confesses that he has fallen for her. Kat forgives him, and they reconcile with a kiss.
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