In the third installment of this series, former classmates from Cardinal Gibson High, a private Catholic school in Fort Lauderdale, are reunited on the beautiful island of Oahu for a 10-year reunion. These former classmates all have something to prove, someone they want to impress and someone they want to avenge. As the group gets settled in, Nikol (The Good Girl) is given the first hall pass, and is nervous about asking her high school boyfriend Jim (The Jock) though they both admit they have unresolved feelings for each other. Nikki (The Head Cheerleader) is also given a hall pass and invites Brien M. (The Rebel) for a night on the town.

Gianni (The Basketball Star) gets a hall pass, and after waiting years, invites Loretta (The Dream Girl) for a romantic night on the beach. But when Jamie discovers the date has lasted all night and the two didn't sleep at the reunion house, Jamie flies into a rage. Back at the house, Carin (The Fat Girl) and Nikki (The head Cheerleader) have different memories of how Carin was treated in school and send her remembering all of her old feelings of being overnight and depressed; when Eze (The Soccer Guy) sees that Nikol and Jim are having problems getting close, he makes his move on her. Two new arrivals, sisters Tara (The Vixen) and Torie (The Hottie), arrive and turn the house into a party starting with a late night swim and a sexy game of truth or dare.

After a decade of waiting, Gianna (The Basketball Star) and Loretta (The Dream Girl) finally get their perfect date. Except when they arrive home, Gianna's ex-girlfriend Jaime (The Obsessed Ex) lashes out at him about spending the night with Loretta. Nikol (The Good Girl) gets a second hall pass and a second chance with Jim (The Jock). Though he's still guarded with his emotions, they finally spend the night together. The next night, the girls are leave the reunion house for a wild slumber party that eventually has some unexpected crashers. While at the party, Loretta (The Dream Girl) receives another secret note and package from her secret admirer and gets whisked away to a private beach to meet him face-to-face.

Five guys from rival Douglas High arrive on the island, including Nikol's (The Good Girl) senior year boyfriend. Tempers and egos heat up during a Cardinal Gibbons vs Douglas High football game that lands Jim (The Jock) in the hospital with a head injury and Nikol at his side. Jen (The Predator) backstabs Nikki (The Cheerleader) when they both find themselves attracted to the same Douglas hunk. Gianni (The Basketball Star) and Loretta (The Dream Girl) share another romantic evening and worry about Gianni's upcoming return to Italy.

Two more classmates, Kristian (The Nerd) and Matt (The Dork), arrive in a red hot Corvette, let the classmates believe they are wealthy Internet moguls and make an impression the girls by bringing personal masseuses to the house. Brien M. (The Rebel), who feels he has connected with Torrie (The Hot Sister), invites her on his hall pass, which includes a romantic dinner, massages and bubble bath. Bill (Douglas Rival) invites Nikki (The Cheerleader) on a hall pass to set the record straight about Jen (The Predator). Nikol (The Good Girl), who is frustrated by Jim's (The Jock) lack of communication, accepts Eze's (The Shy Guy) hall pass invitation, which leaves Jim wondering if he missed his chance with her. Tara (The Baby Sister) tells Brien M. (The Rebel) and Torie (The Hot Sister) that she overheard John (The Loud Mouth) making derogatory remarks about her sister, sending Brien M. into a rage which ends in a nasty confrontation.

The classmates are given one last chance to use a hall pass to invite the person of their choice on a date. Gianni (The Basketball Star) invites Loretta (The Dream Girl) to a romantic garden dinner where she lets him know she doesn't believe in long distance relationships but accepts his surprise ticket to Italy. Brian A. (The Meathead) invites Nikki (The Cheerleader) for a night on the town, and Jim (The Jock) asks Nikol (The Good Girl), where he professes his love and his desire to continue their relationship after the reunion. The rest of the classmates go into town for a night of drinking and pool but soon after arriving, Brien M. (The Rebel) and Torie (The Hot Sister) leave the group in town to spend a romantic night at the estate together. The classmates start making plans for next week's prom.

At the prom, Kristian (The Nerd) and Matt (The Dork) come clean to their classmates about their real financial status, the group is surprised with performance from the popular 1994 band The Gin Blossoms, while Torie (The Hot Sister) and Brien M. (The Rebel) talk about what will happen when they leave Hawaii. Later in the evening, Jen (The Predator) and Jim (The Jock) are caught in a comprising position, leading to an angry confrontation with Nikol (The Good Girl).