Jena Malone plays the role of "Mary" who is a teen who just became pregnant while attending a Christian high school. What complicates the matter is her boyfriend, future father of her unborn baby, turns gay. Mandy Moore is "Hilary Faye," Mary's best friend in the movie, is portrayed as hypocritical as she looks after her wheelchair-bound brother "Roland," played by Macaulay Culkin yet acts in a way to appall Mary such as her attempts to hook-up with a skateboarding missionary. Faye is also trying to covert her Jewish friend "Cassandra," played by Eva Amurri throughout the film.

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