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Roland reveals that he is not really a Christian, unlike his fanatically religious sister.Cassandra reveals she is only at American Eagle after being thrown out of her old school and decided she could "handle the freaks" at American Eagle over being home-schooled by her parents.In homeroom, Mary meets new student Patrick (Patrick Fugit), the son of the school's principal, Pastor Skip Wheeler (Martin Donovan), a skateboarder who has been doing missionary work (through skateboarding) in South America.Mary tries to put up a good front at the assembly, in which Cassandra fakes speaking in tongues in order to get under the skins of the other students.Mary’s "perfect Christian boyfriend" Dean Withers (Chad Faust) tells her, as they’re swimming underwater, that he thinks he's gay.In her shock, Mary hits her head in the pool and has a vision in which Jesus tells her that she must do everything she can to help Dean.
She and her two best friends, Hilary Faye (Mandy Moore) and Veronica (Elizabeth Thai), have formed a girl group called the Christian Jewels.Hoping for a sign, Mary goes to a shooting range with Hilary Faye, who has a "spiritual solution for everything" and tells Mary (not knowing about the situation with Dean) that if all else fails, Jesus could still restore their "spiritual and emotional virginity." Believing that Jesus will restore her purity, Mary sacrifices her virginity to have sex with Dean in an attempt to restore his heterosexuality.Despite Mary's efforts, when she comes by Dean's house on the morning of the first day of school, Dean's parents tell her that they found gay pornography under his bed and that they're sending him to Mercy House, a Christian treatment center.Mary tells her friends, as well as Hilary's brother Roland (Macaulay Culkin), who uses a wheelchair, about Dean's homosexuality, and makes them promise to keep it a secret.When they arrive at school, they see Cassandra Edelstein (Eva Amurri), the school's only Jewish student and a rebel who despises Hilary.
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While working together, Patrick asks Mary to go with him to the prom, which Mary accepts, but as friends.