In this coming-of-age comedy, Tim Dunphy (Shawn Hatosy) is leading a go-nowhere existence, spending his days smoking pot and hanging out with his best friend, Drugs Delaney (Jon Abrahams). But Tim's lazy days of getting high are jettisoned after a brush with the law convinces his blue-collar dad (Alec Baldwin) to send him to a Connecticut prep school. The one saving grace of the new school is Jane (Amy Smart), a fellow student Tim falls for immediately.