Pilot) Jed Perry becomes one of the first boys ever to attend Evergreen Academy when he moves to a new town. He quickly bonds with the only other male students, Cary (Chris Evans) and Phil (Kyle Howard), when the girls, lead by Stella (Lindsey McKeon), ostracize them. But when Miranda Mills (Margot Finley), a free-spirited Sophomore, takes an interest in Jed she helps the boys gain acceptance with a stunt at the annual Evergreen talent show

Virgin episode) Miranda's birthday party is approaching, a legendary event where two virgins are "sacrificed". Jed, the only one of the boys who openly admits to be a virgin, is naturally selected and his friendship with Kate (Allison Mack), another suspected virgin, develops. Meanwhile, Cary, who has been flaunting his sexual experience, becomes the target of Stella's campaign to remove the boys from school. The boys discover that the school has a history of expelling girls with an unwholesome reputation, so they decide to track them down in the hopes of gleaning some information that might save Cary's place at Evergreen

Drug episode) After the boys discover the janitor's stash of marijuana, the school hires a new drug counselor, Greg Tillman (Dax Griffin), to speak with the students. Jed instantly forms a strong dislike of him, due to his good looks and the lust he provokes in the entire student body, including Miranda and Kate. When word gets out that Cary is "hooked up" and he instantly becomes popular with some of the girls, he decides to play up to his new reputation. Meanwhile, Phil runs an ill-fated campaign for city council with a strong position against drugs

Homosexual episode) It's Bow Down week at Evergreen Academy, an annual tradition in which Seniors select a Junior to be their personal slave for a week. Jed is picked by Joely (Nicki Lynn Aycox), an out lesbian, who begins to show a strong attraction to him. Completely confused, he tries to work out whether he's just imagining it. Meanwhile, Cary incures the wrath of popular girl Cassie Schreiber (Joanna Garcia) after he leads a revolt against the seniors, and is threatened with the mythical "360" Dance episode) The boys wonder if they're losing their masculinity. As a school dance approaches, a rift is formed in the boys' friendship when Phil starts to pursue Kate, much to Jed's chagrin. Meanwhile, Cary is humiliated by a student from the nearby military school Fort Union and vows to get revenge

Field trip epsiode) The juniors of Evergreen Academy travel to New York for a Model U.N. summit, where Jed is reunited with his ex-girlfriend, Lisa (Christine Lakin). When Lisa and Kate, Jed's current love interest, become awfully friendly with each other, Cary persuades Jed that a threesome is on the cards. Meanwhile, Phil befriends some boys from Fort Union, and sparks fly between Cary and Stella.

Fantasy episode) When Stella gets severely drunk on Miranda's hidden supply of everclear just as the student body is leaving for a field trip, the boys, along with Miranda and Kate, smuggle her back into the now empty school. With only the supervision of Greg Tillman, the drug counselor who they called to help with Stella, the gang spend the night on the Evergreen campus, where Miranda asks Jed to sleep with her, Phil and Kate bond in the school kitchens, and Cary comes to Stella's rescue

Car episode) When he finds himself dating both Miranda and Kate at the same time, Jed is forced to decide who he really wants to be with. He chooses Kate, but shortly afterwards she learns about his two-timing and breaks up with him. Phil, with his eye on the newly single Kate, decides that he needs a driver's license to win her heart. Meanwhile, Cary and Stella are forced to cater to a band geek's every whim in order to keep their relationship secret. Having finally decided on Kate, Jed goes to extreme lengths to try and get her back.