Kevin is worried that Paul will look foolish when he's drafted to the basketball team, but it appears that Paul is only at his worst when he plays Kevin.

Kevin is excited when a joint field trip is organized with Winnie's school. But things do not work out so well when Kevin has a hard time tearing Winnie away from her new friends. Things go from bad to worse when Winnie tells Kevin she has met someone else.

Kevin and his father endure a disastrous trip together to buy a suit for Kevin. They get lost and argue over the radio station and Kevin embarrasses Jack at a diner they stop at.

Kevin finds himself in the in-crowd when he is invited to write witty captions for the photos in the yearbook. But when it comes to writing one for the fat kid in school, Peter Armbruster, Kevin has a hard time figuring out what is funny and what will hurt Peter.