Shawn's life is a mess when his dad takes a job as a school janitor, so Mr. Feeny offers to let him decide his father's career fate.

To take his mind off his dad's death, Shawn takes Cory along on a soul-searching road trip in Chet's trailer, where they end up at a truck stop where the young waitresses (portrayed by band Nobody's Angel) are searching for something more, just like Shawn -- and Cory discovers that Shawn has no intention of returning home. Shawn must persuade Cory to let him go, just as the girls' father/boss must let them find their own way. Meanwhile, Eric tries to understand the kiss he witnessed between Jack and Rachel -- as do they; and Shawn discovers that his father, a truck stop regular, was secretly very proud of him. In a surprise code, Chet's ghost appears to Shawn as father and son finally reconcile their differences and Shawn drives off into his uncertain future.