Boy Meets World S06 E15 Road Trip

"His older brother likes girls. His younger sister likes dolls. His parents like rules. And he'd like to know where he fits in."

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 are searching for something more, just like Shawn -- and Cory discovers that Shawn has no intention of returning home.