When Kevin thinks the best he can do in math is a B, his teacher Mr. Collins sets him the task of getting an A and even offers him private lessons. When Mr. Collins suddenly pulls out of the lessons shortly before the exams, Kevin feels betrayed and fills his exam with nonsensical answers.

After Kevin loses all his money and his car in a poker game, he decides he has to leave the resort - there's nothing to keep him there now. The next day he says goodbye to Winnie, punches Eric and storms out. Hitchhiking out of town, he runs into Winnie who has been fired from her job. They begin to argue and lose the ride they had flagged down. Later, sheltering in a barn they talk about how much has changed between them. Winnie thinks it's just inevitable - that everyone grows up. Kevin doesn't want to believe it and neither does Winnie, not really. They kiss, passionately. The next day they both return to Kevin's hometown for the last 4th of July he will ever spend there. Karen has returned home and she is pregnant...

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."

Kevin and Paul attend Robert F Kennedy Junior High for the first time. Winnie's brother is killed in Vietnam. Kevin and Winnie kiss for the first time.

Kevin wants to take Susan Fisher to the dance, but she has a boyfriend, Donald Wallach. However, he hears rumors that they have broken up, so he's about to ask her until Donald interferes. Linda Sloan, his lab partner, suggests that they go as friends so they do. They have a good time in the beginning, but it turns sour when while Linda is dancing with Steve Padway, Kevin dances with Susan and they have punch. How is it bad? Susan leaves and Linda comes back and asks if they half-filled cup of punch that Susan left is for her, but Kevin says that it's Susan's in a not-so-nice sort of way. That basically breaks Linda's heart and she leaves. Kevin is about to ask Susan to dance again but she's dancing with Donald, so Kevin leaves, not knowing that Winnie came in, probably looking for him.

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 isn't sure whose side to take when Karen decides to enroll in a liberal college and Jack is dead-set against it.

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 learns more about his dad by spending a day at his office.

Kevin wants to know if Winnie likes him or Kirk. Kirk wants to know if Winnie like him or Kevin. Becky punches Kevin when she finds out he doesn't really like her.

When Kevin is partnered with class weirdo, Margaret Farquhar, he tries to keep away from her - especially when she tries to become his friend.

Kevin enters uncharted waters when he meets an older girl during his summer vacation.

To make up for being rude and insenstive to Winnie, Kevin makes her a Valentine's card, but it is accidently placed in Becky Slater's locker. When Becky finds the card, she thinks Kevin wants her back - setting the two up for a showdown.

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.

The Arnold and Pfeiffer family go on a joint family trip. Kevin meets a wild young girl who smokes! Kevin and Cara have a good time together, so much so that he ditches dinner with his family to see her one last time - expecting to never see her again.

While Kevin is asked to consider his future, Wayne makes a decision to leave school and join the army. Jack and Norma try to talk Wayne out of it, but he won't listen. Wayne and his friend Wart go together to the army testing station. Jack follows and apologises to Wayne for not being a better father to him.

While Kevin tries to take his relationship with Winnie another step, Wayne's friend Wart returns from Vietnam a changed man. Kevin decides to steal the opposing team's mascot at the homecoming football game, but the childish prank is overshadowed by a realization of how Wart has been affected by the war.

Norma begins taking a pottery class, but receives no support or encouragement from Jack.

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 has trouble in math class when he comes up against a teacher who Kevin thinks is completely unreasonable.

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

Kevin wants to date Inga and he uses Winnie to help him get a date. Winnie does the same thing to Kevin, getting set up with new guy Matt Stevens. They end up double-dating at the Spring Dance, bringing some tension to the evening. But when Matt and Inga begin to dance together, Winnie and Kevin rediscover their feelings for each other.

While passing notes during class, Kevin asks Lisa Berlini to go to the dance with him. She says okay, but she decides to go with Brad Gaines after he asks her. While eating lunch with Winnie and Paul, Kevin feels himself falling back in love with Winnie, but she is goes to the dance with Kirk McCray. Kevin tries to make Winnie jealous by dancing with an unidentified girl...

Kevin continues to pine for Winnie, but is becoming frustrated with being alone - especially as Paul has Carla. Even though he's just looking for someone to make Winnie jealous, he ends up boyfriend to Becky Slater.

Kevin learns a lesson about talking behind someones back and how 'hell hath no fury like a woman scorned'.