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Ian Lafferty (Josh Zuckerman) is an 18-year-old recent high school graduate. He searches for a girl online making it look as if he’s buff and suave, although he’s sweet and unassuming. He soon meets "Ms. Tasty" (Katrina Bowden) and agrees to meet her in person. She lives in Knoxville, while he lives in Brookfield. With his best friends Lance (Clark Duke) and Felicia (Amanda Crew), they go in a Pontiac GTO borrowed without permission from Ian’s arrogant homophobic older brother Rex (James Marsden).

On the way the car is damaged. It is repaired for free by Amish people, while they join a Rumspringa party at which Fall Out Boy is playing a concert. The three promise to come again on the way back to do some work in return. Lance falls in love with Amish girl Mary (Alice Greczyn).

They go to jail for accidentally damaging a police car, and are released after Mary pays the bail. They find a hotel that sports a wide variety of role playing rooms. Rex arrives angrily and insists that they go back and that Ian cannot visit Ms. Tasty. After Ian pretends to be gay, Rex allows him to see Ms. Tasty, hoping this encounter will change Ian’s mind. However, they are scammed by Ms. Tasty and her psychotic boyfriend, who apparently do this to steal cars for chop shops. Ian saves the day, Ms. Tasty and her boyfriend are arrested, and Ian and Felicia realize they love each other. Lance refuses to go back home at the end of the trip and stays behind to marry Mary. Ian gives his virginity to Felicia, who both reveal their love for each other at the end of the film. Also we learn Rex’s latent homophobia stemmed from the fact that he was harboring his own homosexuality. At the end of the film, a picture is shown of Lance and Mary being married, accompanied by Ian and Felicia. He’s shown sporting a beard much like Ezekiel (Seth Green), one of the Amish people. During the credits there is a clip of Ezekiel and Fall Out Boy arguing over the fact that the Amish fixed Fall Out Boy’s tour bus and all that they got in return was "a five song set."