The family attends Jack's company picnic. Kevin is not looking forward to seeing Mimi Detweiler, who used to have a crush on him. Wayne's new girlfriend Angela annoys everyone but Wayne. Kevin beans Jack with a baseball at the father-son baseball game. Karen leaves for college.

Winnie is nervous about starting a new school, so she gets Kevin to promise to think about her every hour on the hour. Kevin finds this promise harder to keep than he thought when he loses his locker to Tony Barbella, is enrolled in shop class and meets a new girl in French class, Madeline.

News of a 10th-grade girls' slumber party has Kevin and his friends traveling across the city, believing they'll be invited in if they bring beer.

When Kevin learns that Paul gets a weekly allowance of five dollars and that there is money to be made being a caddy, he goes to work for the first time.

Kevin has to cancel a date with Winnie to finish a homework assignment with Madeline, who has already kissed him once. To make matters worse, when he flees Madeline's, he drops a bracelet that Winnie had engraved for him.

Paul's sister Debbie needs someone to take her to a cotillion and Kevin is guilted into the task. Meanwhile, Paul, Doug and Randy go to the football game to watch cheerleader Donna Delgado.

When the family needs money, Jack demands a raise and gets it. But his new position means travelling across the country and it looks like he might miss Thanksgiving.

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 discovers a soft-spot inside Cutlip when he sees him playing Santa Clause at a local mall.

Kevin enters the race for student-council president, head-to-head with nemesis Becky Slater.

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.

News of Kevin's break-up with Winnie has spread quickly throughout Robert F Kennedy Junior High. Kevin is still in denial though and has Paul organise a party at his place so that Kevin can get Winnie alone. In an effort to make Winnie jealous, Kevin turns up with Madeline on his arm. When Kevin finally does get Winnie alone, she tells him she needs him to be her friend, but only her friend.

Kevin learns the importance of family when Grandpa Arnold returns to town for Aunt Rose's funeral.

Kevin has a small crush on Dr. Tucker's dental hygienist, Miss Hasenfuss. She makes him feel like a man, though that all changes when she calls him in for his first cavity filling.

Kevin's dog Buster needs to get fixed to stop his incessant barking, but the dog wants to avoid that at all costs.

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's quest to remain cool is shattered when Norma takes a job at his school. He tries to rebel by stealing a hallpass for Tony Barbella, but Norma catches him in the act. When Norma acknowledges him during a fire drill and the other kids laugh, Kevin decides it is time to ask his mother to stop noticing him at school.

When Kevin and Wayne decide it's too cramped for two grown boys in their bedroom, they decide one of them should be allowed to move into Karen's room, now that she's away at college. The trouble is, who is going to be the one to go?

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.

Kevin sees Winnie for the first time since they broke up. He discovers that she a Roger have split up, too. When Winnie is in a car accident, Kevin rides over to see her at home, but her parents say she doesn't want to see him. Kevin leaves, but returns and climbs up to Winnie's bedroom window. They tell each other, "I love you."

Jack wants to help Karen out by fixing up the house she is now living in. But father and daughter go head-to-head when he discovers she is living there with a man.

As Kevin graduates from Junior High, he wants to believe nothing will change, but he learns that things can and do change when he discovers Paul is going to a private school in the coming year. Winnie is also anxious about the future. And Kevin has to drive Mrs. Heimer to the hospital when she goes into labor.