A clip show of highlights from Kevin's years in Junior High. Including clips from "Don't You Know Anything About Women," "The Glee Club," "Just Between You and Me... and Kirk and Paul and Carla and Becky," "Summer Song" among others.
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.moreless
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."moreless
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.
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'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.moreless
News of Kevin's break-up with Winnie has spread quickly throughout Robert F. Kennedy Junior High. Kevin is still in denial and has Paul organize 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.moreless
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 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.
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, Madeleine.moreless
The family attends Jack's company picnic. Kevin is not looking forward to seeing Mimi Detweiler, a girl 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.
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