 Mary Bradford (Mischa Barton) is a shy, naive, freshman newcomer to a fancy girls boarding school where she strikes up a friendship with her two senior roommates, the overachieving Tori Moller (Jessica Paré), and the voraciously poetry reading, unapologetic, closeted lesbian Paulie Oster (Piper Perabo). As Mary tries to adjust to her new suroundings, with some guidence from the local groundskeeper Joe Menzies (Graham Greene), she soon learns that Paulie and Tori are lovers. When Tori, under pressure from her classmates, wants to break it off with Paulie, she resorts to extreme measures to win Tori back.