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Dave, Sam and Jeff are about to graduate from Holden University with honors in lying, cheating and scheming. The three roommates have proudly scammed their way through the last four years of college and now, during final exams, these big-men-on-campus are about to be busted by the most unlikely dude in school. Self-dubbed Cool Ethan, an ambitious nerd with a bad crush, enters their lives one day and everything begins to unravel.
Fired from his band and hard up for cash, guitarist and vocalist Dewey Finn finagles his way into a job as a fifth-grade substitute teacher at a private school, where he secretly begins teaching his students the finer points of rock ‘n’ roll. The school’s hard-nosed principal is rightly suspicious of Finn’s activities. But Finn’s roommate remains in the dark about what he’s doing.
An advice columnist, Andie Anderson (Kate Hudson), tries pushing the boundaries of what she can write about in her new piece about how to get a man to leave you in 10 days. Her editor, Lana (Bebe Neuwirth), loves it, and Andie goes off to find a man she can use for the experiment. Enter executive Ben Berry (Matthew McConaughey), who is so confident in his romantic prowess that he thinks he can make any woman fall in love with him in 10 days. When Andie and Ben meet, their plans backfire.
Brooks Caldwell, (Cary Elwes) an erudite and handsome lawyer, seems to have it all: wealth, social status and a red hot career. His success is, in reality, a product of his marriage to his beautiful, socialite wife, Amanda, (Terri Polo) a wealthy timber heiress. Unlike most, who would remain content to enjoy a life of luxury and privilege, Brooks continues to risk everything by having extramarital affairs. Brooks’ philandering, in addition to humiliating Amanda, has driven her to the point of a mental breakdown. Having been pushed over the edge, Amanda orchestrates a just and elaborate plan to bring her husband down. When Brooks leaves for a weekend romp with his latest squeeze, (Agnes Bruckner) his life quickly descends into a bizarre, nightmarish, downward spiral.