Winnie takes a summer job as a life guard at a hotel resort, while Kevin considers a cross-country trip with his friends, an idea that Jack soon quashes knowing that Chuck and Jeff is cross-country without Chuck's Own Parents and Jeff's Mother's permission. Frustrated, Kevin then quits his job at Jack's factory and drives to the resort to see Winnie. Kevin then takes a job as a waiter to be near Winnie, but is then disappointed when he and Winnie are so busy they have no time for each other. Kevin gambles his gas money playing poker with the resort's house band and manages to win big; but later, when he finds Winnie to tell her of his good fortune, he becomes shocked to see Winnie kissing a co-worker. Part one of the two-part series finale.