The Girl in Lovers Lane (1960)

Danny, son of a wealthy family, is running away from home. He meets Bix, a long-time drifter, who agrees to "mentor" Danny. Danny's naivete leads him to commit gaffe after gaffe, leaving Bix to straighten things out. But when they stop in a diner in the next town, Bix finds himself attracted to the waitress, Carrie, and is forced to reexamine his whole drifting career. Meanwhile, Jesse (Jack Elam) goes around creeping everyone out.