Kevin had been having recurring nightmares about finding himself in a cave and ending up in the middle of his class dressed in some ridiculous way. Meanwhile, he attempts to act cool after Winnie starts dating Kirk McCray (Michael Landes) and hanging out with all the cool kids. Kevin and Paul go camping with Gary (Breckin Meyer), where they drink beer and smoke cigarettes. When Gary invites Kevin and Paul to explore a "cave" (which is actually a long huge storm drain), Kevin must confront his fears of the cave. In the end, Paul and Kevin end the outing and go back to Kevin’s house. The next day they see Winnie and they have a few laughs together.

Kevin develops a student-teacher crush on his nice English teacher, Miss White (Wendel Meldrum), who persuades Kevin to play the lead role of Robert Kennedy in a school play she wrote.

Kevin and Wayne try to talk their father into buying a color television for Christmas; but it’s not easy, as the TV costs $470.00 (about $3,100.00 in today’s currency). Meanwhile, Kevin tries to find a present for Winnie after he unexpectedly receives one from her. After debating on which perfume to buy her, Kevin settles for a small water globe containing a miniature figure skater. But when Kevin takes it over to Winnie, he is surprised to find that Winnie is not there to receive the present (turns out that the Coopers unexpectedly left town for Christmas because they could not bear spending their first Christmas home without Brian). Kevin leaves the present with their housesitter and then joins his family for a night of caroling--although they get rained on by an out-of-season thunderstorm. By the episode’s end, it is revealed that Jack did buy the color TV--two years later.

Rumors spread that Winnie and Kirk are about to break up. When Kevin finds out, he sees the situation as an opportunity that he and Winnie can perhaps get back together. Later, during choir practice, Kevin notices Winnie smiling in his direction while singing; but is disappointed when he turns around to see Kirk holding up a sign saying "I’m sorry, Winnie" through the classroom door. Kevin then gets frustrated with being alone, and asks Becky Slater (Crystal McKellar, Danica McKellar’s real-life sister) to go steady, primarily to try to make Winnie jealous. Meanwhile, Paul starts dating Carla Healey (Krista Murphy). Part one of two.

Kirk McCray asks Kevin to find out whether or not Winnie still likes him. While speaking to her, Winnie tells Kevin that she will break up with Kirk soon. However, Kevin sees Kirk and Winnie kissing in the hall. Meanwhile, Becky Slater becomes furious and punches Kevin when he tells her that he just wants to be friends instead of going steady. Kevin still wants to find out if Winnie likes him, but she is confused and not sure. Part two of two.

When Norma decides to take a pottery class, Jack is less than happy for his wife, which deeply disappoints her. Her disappointment, along with Jack’s built-up anger, leads to the couple’s first big fight in front of the kids. This episode marks the debut of Ben Stein’s recurring role as Mr. Cantwell, Kevin’s mono-toned science teacher, who is teaching about natural disasters which worries Kevin and Paul.

Kevin dislikes his piano lessons, until his chain-smoking instructor Mrs. Carples (Maxine Stuart) tells Norma that Kevin has talent. He continues taking lessons, and improves his playing. That is, until Ronald Hirschmuller (Joseph Dammann) decides to play the same piece as him for the recital. After he messes up at the rehearsal, Kevin decides to quit and not go to the recital, a decision he seems to regret later in life.

Wayne’s bullying goes too far when he tortures and kills Kevin and Paul’s hamster test subject of an experiment for their science class. The incident lead to an outburst from Kevin which, although it did emotionally hurt Wayne, it finally led to a change in Wayne’s attitude towards bullying Kevin--or did it?

Paul likes to play basketball, but unfortunately he’s not very good at it; therefore, during team-organizing, Paul is always picked last, which bothers Kevin. So Kevin complains to Coach Cutlip (Robert Picardo) about the unfairness of team-organizing, but to no avail, as Cutlip informs Kevin that "life is not fair." However, Cutlip picks Kevin as a captain, and in fairness he attempts to pick his team members so that Paul and the other bad players are not always picked last, thereby choosing all the bad players for his team.

Kevin and other students on the student council try to organize a peace walk out to protest America’s involvement in the Vietnam War with the "blessing" of the "coolest" teacher in the school. However, Mr. Diperna (Raye Birk), the school’s vice-principal, threatens to suspend students that do this and then "mark it down on their permanent records" if they take part in it.

Kevin learns a lesson about talking behind someone’s back and making jokes about his friends. He realizes that "hell hath no fury like a woman scorned" when Becky Slater--obviously in retaliation for Kevin breaking up with her, which she still holds a grudge on Kevin for--tells everyone what Kevin said about them. Worried that Becky also told Winnie what Kevin said about her as well, Kevin hurries to Winnie’s on the way home from school to try to straighten it all out. Upon learning that Winnie became ill with a stomach virus, Kevin visits her every afternoon until she gets better. However, Kevin also becomes stricken with the virus, obviously as a result. Winnie returns the favor and visits Kevin at his house, but when Norma leaves them alone in Kevin’s room, Winnie furiously turns to Kevin and scolds him severely for making jokes about her, indicating that Becky told Winnie about what Kevin said about her, as well. Part one of two (sort of).

Winnie is still angry with Kevin for talking about her behind her back; but even so, Kevin defends her honor against school bully Eddie Pinetti (Bobby Jacoby). Kevin is then shocked to find out that Winnie and Eddie are dating; but in the end, Kevin’s loyalty wins back Winnie’s friendship when he stands up to Eddie and fights him for teasing Winnie--even though Kevin loses the fight itself. Part two of two (sort of).

When Kevin’s 13th birthday falls on the same day as Paul’s Bar Mitzvah, he feels left out, especially since his family isn’t really planning anything, but also becomes interested in family traditions and questions where his ancestors came from. Kevin at first rejected the invitation to the Bar Mitzvah, but he at the last moment he showed up a few minutes into Paul’s recitation. Then he has a sense it is his own due to his involvement with an important event for Paul.

Kevin becomes Karen’s confidant and accomplice when he discovers she is skipping school with her friends Julie (Devon Pierce) and Sandy (Kyra Stempel) to spend time at their hippie hangout, known simply as "the hill." Kevin becomes concerned about covering for Karen after repeated encounters in the hallway of Karen’s school with George Finch, a slightly long-haired man in trendy clothes who looks young enough to be a student, but who is actually a faculty member and advisor investigating Karen’s truancy. Meanwhile, chaos ensues overnight at the Arnolds’ when Kevin is awakened by Jack’s frantic telephone calls attempting to track down Karen, who has run away. After a while of telephone investigations, it was discovered that Karen attempted to run away with her friends to San Francisco--but she doesn’t get very far, as she returns home later that night, in tears.

When Kevin is partnered for square dancing with nerdy Margaret Farquar (Lindsay Fisher), he tries to avoid her--especially when she tries to become his friend, and also when Kevin’s friends--and Wayne--tease him about her. Later, Kevin panics when Margaret unexpectedly shows up at his house, but after a while of visiting, Kevin finds out that Margaret is actually pretty interesting to talk to; however, Kevin’s self-consciousness of "the rules of popularity" forbid them to remain friends and Kevin ends up literally ditching Margaret the next day at school, deeply offending her.

Kevin, Winnie, and Paul try to stop the destruction of Harper’s Woods, their childhood hangout, which the city is developing for a new shopping mall. They don’t want it destroyed because it was the place where Winnie and Kevin hold sentimental after sharing their first kiss and also a place they all played together when they were younger. At Karen’s suggestion; Kevin, Winnie, and Paul attempted to voice their concerns at a town meeting but fell asleep until after the meeting was adjourned. At school the next day, Kevin was caught by Mr. Diperna for not looking where he was going in the halls and was forced to "think about what he had done" in Mr. Diperna’s office, where he gets into further trouble for carving his initials on Diperna’s desk. After all of this; Kevin, Winnie, and Paul sneak outside to visit Harper’s Woods one last time before it’s demolished. The final scene in the episode shows the present-day shopping mall on the site of what had once been Harper’s Woods, with the kids’ initials carved in a sidewalk, as they had been on a tree in Harper’s Woods.

It’s the end of seventh grade for Kevin and a summer full of changes in his life. Winnie’s parents, Mr. and Mrs. Cooper (H. Richard Greene and Lynn Milgrim, respectively), are separating and Kevin’s favorite teacher Miss White announces she will be getting married over the summer and her new name will be Mrs. Heimer (spelled a few different ways). Paul and his family leave for an extra long vacation for supposedly the entire summer, and Winnie and her mother will be spending the summer in Maine. So this leaves Kevin sulking about having nothing to do and no one to spend his summer with.