It's the end of seventh grade for Kevin and a summer full of changes in his life. Mr. and Mrs. Cooper are breaking up and Miss White announces she is going to get married.

Kevin, Paul and Winnie become involved in a production of "Our Town." Trouble begins when Winnie gets stage fright. Kevin thinks he's set because all he has to do is operate the spotlight.

Pressure is brought to bear on Kevin and Winnie's relationship when they are invited to a notorious make-out party.

When Jack begins to complain about dry rot in the house, Kevin begins to think that his father might consider moving. When it is revealed that the Arnolds are staying put and it is the Coopers who are moving out, Kevin buys Winnie a ring as "insurance." Kevin decides to attend Karen's graduation from high school rather than watch Winnie leave.

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."