Mary (Jena Malone) is a good Christian girl who goes to a good Christian high school in Baltimore where she has good Christian friends, mainly Hilary Faye (Mandy Moore), and a perfect Christian boyfriend, Dean (Chad Faust). Her life seems perfect, until the day that she finds out that Dean may be gay. After "seeing" a vision of Jesus in her pool, she does everything in her power to help him turn straight, including offering up her virginity. But none of it helps because Dean's caught and sent to a "degayification" center and Mary ends up pregnant. It's during her time of need that she becomes real friends with the school's set of "misfits," including Cassandra (Eva Amurri), the school's only Jewish girl; Roland (Macaulay Culkin), Hilary Faye's wheelchair bound brother, and Patrick (Patrick Fugit), the skateboarder son of the school's principal, Pastor Skip (Martin Donovan); whilst Hilary Faye turns her into a social outcast.