Prep school bad boy Larsen breaks up with his girlfriend Gabrielle. Depressed and lonely, Larsen becomes friends with shy drama kid Jack, much to the dismay of Jack's best friend Rachel.
As a new semester begins, Larsen's back with Gabrielle and too busy to notice Jack. But the arrival of transfer student Edgar turns the tables. Meanwhile, Larsen's best friend Fareed pursues Gabrielle.
While Jack and Edgar have a highly charged sleepover, Larsen discovers the truth about Fareed and Gabrielle. A confrontation may bring Jack and Larsen together, or push then even further apart.
Jack's devotion to soccer...and Larsen...takes a toll on his relationship with Edgar. Gabrielle also tries out for the soccer team with the help of Rachel, but her motives are deeper than love of the game.
Jack directs his first play, Shakespeare's Romeo and Juliet, but finds his love of theater may threaten his friendship with Larsen. Gabrielle and Edgar grow closer as co-stars portraying the doomed lovers in the play. Rachel counsels Jack when things turn sour with both Larsen and Edgar.
Edgar plans to take Gabrielle to the prom, but Rachel reveals a secret that sends Gabrielle into a drunken rage. Jack and Larsen struggle to hide their feelings for each other. At the prom, the rivalry between Edgar and Larsen boils over into violence. After Gabrielle confronts Jack about Larsen, Jack presents Larsen with a final ultimatum.
A devastating tragedy strikes as the school loses one of its own. Everyone feels this loss, but some take it worse than others as they prepare for the annual Senior Tea. Larsen is consumed with guilt. Jack turns to the bottle. Fareed returns from the sanitarium. And Cecelia, a mysterious, beautiful new student, transfers to the academy.
Lunch hour at the academy. Jack now rules the school with his new "best friend" Gabrielle. Larsen tries to make amends and reclaim his lost reputation. Fareed and Gabrielle use Rachel as a pawn in their games to make each other jealous. Cecelia goes after the man she loves and she's not going to let anyone stand in her way.
Gabrielle and Rachel put together a surprise party for Jack's eighteenth birthday. Fareed finds himself in an awkward situation, caught between the two girls that want him. Larsen finally realizes the truth about his new girlfriend Cecelia. Jack gets an unexpected message. Larsen arrives at Jack's surprise party with a something very special to say to the birthday boy. Rachel walks in on a compromising situation between Fareed and Gabrielle. Cecelia crashes the party, bent on revenge. Once the night is over, nothing will ever be the same. The prep school kids must stand together for the first time or fall apart for the last.