A high-school senior drives cross-country with his best friends to hook up with a babe he met online.

Ian, a high-school senior in suburban Chicago, is plagued by being a virgin. Online he's inflated his resume, met Ms. Tasty, and agreed to drive to Knoxville, where she promises sex. He steals his homophobic macho brother's GTO and heads south with his two best friends, Lance and Felicia. Every young woman who meets Lance, including Felicia, is attracted to him as he practices his aptly learned "Pick-Up Artist" skills. Ian, on the other hand, is a decent guy who wouldn't mind if his friendship with Felicia became a romance. By the time they get to Knoxville, they have encountered a jealous boyfriend, a menacing hitchhiker, jailbirds, carjackers, an Amish community, and Ian's better judgment.

A guy gets more than he bargained for after entering into an affair with the wife of an investment banker. Soon, a suspicious death and substantial life insurance policy embroil him in a scandal.