In the typical high school setting of John Hughes High, located in sunny Southern California, the stunning Priscilla (Jaime Pressly), a prominent cheerleader, ends her relationship with her talented yet lackadaisical football boyfriend, Jake Wyler (played by Chris Evans). Jake, often seen as "The Popular Jock," becomes furious when Priscilla begins dating the awkward but charming Les (Riley Smith), also known as "The Beautiful Weirdo," simply to get back at him. Fueled by a bet made between Jake's friend, Austin (Eric Christian Olsen), and Jake, the challenge becomes to turn Janey Briggs (Chyler Leigh), who is affectionately referred to as "The Pretty Ugly Girl," into the new prom queen. Janey, a uniquely rebellious young woman, finds herself at the center of Jake's plan to win over Priscilla.
At the same time, Priscilla takes in Sandy Sue (JoAnna Garcia), "The New Girl in School," who unfortunately has Tourette's syndrome. Jake is haunted by past traumas from a football game where he defied his coach, leading to disastrous consequences for a rookie player. In a moment of self-doubt, Janey confides in her father about potentially dating Jake after being ignored by him for six years. Her father's humorous advice—expressing that Jake’s intentions might be purely physical—sets the stage for a tangled series of events.
As Jake attempts to win Janey's heart, trouble brews both from his own sister, Catherine (Mia Kirshner), who harbors her own disturbing crush on him, and from Janey’s persistent admirer, Ricky Lipman (Eric Jungmann). In an effort to help her brother out, Catherine notably "transforms" Janey's appearance by simply removing her glasses and changing her hairstyle. Meanwhile, Janey's younger brother, Mitch (Cody McMains), and his friends plan to lose their virginity before graduation while trying to woo the lovely Amanda Becker (Lacey Chabert) with a romantic love letter.
The turning point arrives when Jake takes Janey to a party post-transformation, only to have her humiliated by Priscilla. Following a heart-wrenching moment where Jake attempts to comfort Janey, their relationship takes a drastic turn when she’s nominated for prom queen. However, Jake’s recent failures on the football field and a betrayal from Austin complicate their budding romance, leading to a dramatic fallout on prom night.
With tensions running high, the much-anticipated prom sees unexpected alliances and betrayals unfold. Jake discovers that Janey’s outburst causes her to leave, leading him to chase after her only to find himself grappling with deception and misunderstandings. In a frantic race against time, he arrives at the airport just as Janey is about to board a flight to Paris for art school. In an effort to convince her to stay, he attempts to charm her with cliched movie quotes, culminating in a heartfelt moment of connection.
The film concludes with hilariously chaotic moments, including Janey's father, Mr. Briggs (Randy Quaid), experiencing a pie-related mishap, plus a lighthearted post-credits scene featuring the already quirky Albino Folk Singer who is now in a peculiar predicament. The tangled web of teenage romance, rivalry, and personal growth comes together in a story that balances humor and heartfelt moments, much like the memorable films of the past.
