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.

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.

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.

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.

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 Karen has agreed to marry Michael, she has not agreed to have a traditional ceremony like her mother wants. She also doesn't know how to tell her family that she and Michael are moving to Alaska, where he has found work.

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 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.

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 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.

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.

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...