Ian is a high school senior in suburban Chicago, 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, with his two best friends, Lance and Felicia, heads south. 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, jail birds, carjackers, an Amish community, and Ian's better judgment.

A mysterious criminal rolls into a small town planning to knock off the local bank, assuming it will go off without a hitch. But when he encounters a retired poetry professor, his plans take an unlikely turn. With no place to stay, the professor generously welcomes him into his home. As the two men talk, a bond forms between these two polar opposites, and surprising moments of humor and compassion emerge. As they begin to understand each other more, they each examine the choices they've made in their lives, secretly longing to live the type of lifestyle the other man has lived, based on the desire to escape their own.