Winnie gets a summer job at a resort where she will also live. Kevin meanwhile plans a cross country trip with his friends, an idea that his father put a stop to. Kevin then quits his job at his dad's factory and gets a job at the resort where Winnie works. Kevin is then disappointed when he and Winnie are so busy they have no time for each other. Meanwhile, Kevin gambles his life savings playing poker with some pros and wins big, which cheers him up until he catches Winnie kissing a co-worker.