Karen doesn't communicate with her parents anymore. It's made worse when she brings home a new boyfriend. Kevin takes an immediate dislike to Louis.

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 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.

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.

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?

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.

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.

Some people never find true love, but Kevin believes he did. He had what most people search all their lives for, but he blew it. When Winnie comes over for a study session while his parents were away, Kevin wants to relationship to go further. Winnie sees through his plan. She does stay, but they just fall asleep together. The next day, though, he tells his friends a different story. When Winnie finds out, she dumps him.

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.

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.

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 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.

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'.

Kevin does not understand why Wayne's new girlfriend, Sandy, is with him. The tables are turned when Sandy approaches Kevin behind Wayne's back and kisses him. In fact, they kiss all over the school. But when Sandy breaks up with Wayne to be with Kevin, Kev can't bring himself to betray his brother.

Kevin and his brother try to convince their Dad to buy a color television. Kevin tries to find a present for Winnie after she unexpectedly gives him a present.

Kevin and other students on the student council try to organize a walk out to protest America's involvement in Vietnam. Mr. Diperna threatens to mark it down on their permanent records if they do it.

Fed up with the low pay at his first regular job, Kevin decides to try for a job at the mall where he can meet girls. He demands a pay rise, not expecting to get it. When he does, he quits anyway.

When Kevin's parents go away for the weekend, he invites his friends around for a poker game. But when the game gets boring, Chuck and Ricky call all their friends and Kevin ends up throwing the mother of all parties at home - ruining the house. Norma and Jack return the next day, earlier than expected.

Kevin gets a crush on Miss White. She convinces him to play Robert Kennedy is a play she has written.

Kevin strives to prove himself better at the piano than Ronald Hirschmuller. But who is he trying to impress more - himself or his teacher?