 In a Christian school (not Catholic), the fanatic and wealthy Hilary Faye (Mandy Moore) and Mary (Jena Malone) are best friends. Their friendship ends when Mary gets pregnant, after having sex with her gay boy-friend trying to "save" him, and questions Jesus  will. Meanwhile, the rebel Jewish Cassandra (Eva Amurri) dates Hillary s brother, the crippled Roland (Macaulay Culkin), and together with the newcomer son of the local pastor, Patrick (Patrick Fugit), they become the new friends of Mary, supporting her situation.