Kevin joins the school's soccer team in an attempt to become involved in school sports, but becomes very frustrated with the team's lackluster performance and an extremely apathetic coach.

Kevin gets jealous of a charismatic political campaigner who has encouraged Winnie to help him out.

The Pfeiffer and Arnold families have always been friends, but that friendship is threatened when the Pfeiffers come into a lot of money due to a real estate investment that Jack Arnold passed on. When the Arnolds are invited to the Pfeiffers' country club, Jack cannot handle it. Norma saves the day with a toast to the families' continuing friendship

Kevin learns the importance of family when Grandpa Arnold returns to town for Aunt Rose's funeral.

Kevin has a small crush on Dr. Tucker's dental hygienist, Miss Hasenfuss. She makes him feel like a man, though that all changes when she calls him in for his first cavity filling.

Kevin's dog Buster needs to get fixed to stop his incessant barking, but the dog wants to avoid that at all costs.

A clip show of highlights from Kevin's years in Junior High. Including clips from "Don't You Know Anything About Women," "The Glee Club," "Just Between You and Me... and Kirk and Paul and Carla and Becky," "Summer Song" among others.

Kevin is torn between whether to try getting back with Winnie or just enjoying his time at the diner with friends. Includes flashbacks of Winnie in the pilot, "Steady as She Goes," "Nemesis," "How I'm Spending My Summer Vacation," among many others. There is also a flashback to Becky Slater in "Just Between You and Me and Kirk and Paul and Carla and Becky," to Lisa Berlini in "Dance with Me" and to Madeline in "It's a Mad, Mad, Madeline World."

When Kevin is offered a great deal on a used car from Alice's dad, Pistol Pete, Kevin has to decide whether to betray his friend, Chuck, who has broken up with Alice again.

The Arnolds fly across country so Norma can attend her 25-year class reunion. Her parents keep talking about her old boyfriend, Roger, which upsets Kevin, but not Jack. Kevin realizes that the bond between his parents is stronger than he realized.

Kevin is looking forward to the visit of an old family friend, Gina, until he discovers his first pimple.

A new student teacher tries to make something of the 8th-grade boys' Glee Club, but without much success.

When Ricky Halsenbach turns 16, Kev and friends decide to go cruising for chicks. Kevin gets into trouble with Cindy after she catches him in a lie. Purdle moons Kevin's parents from Ricky's car.

When the Arnolds attend the wedding of Jack's boss' daughter, one of the bridesmaids turns her attention to Kevin. He tries to get a bottle of champagne for them to consume together, but ends up drinking it while he waits for her. When she does arrive, Kevin vomits on her. Later, Wayne tells Kevin that he's had sex with the bride.

While Kevin and Winnie are concerned about their futures, Jack gets a disappointing evaluation from his employers at NORCOM. Kevin doesn't want to end up in a job like his dad has and Jack is getting pretty tired of it, too.

On the way to the Planetarium, Kevin and Winnie and Alice and Chuck play "Truth or Dare." When Winnie asks Kevin what he'd change about her, he thinks and then says sometimes she is just too perfect. She doesn't appreciate this and tries to prove that she make trouble as well as anyone else.

Over a game of poker we learn some truths about Kevin's friends, including that Chuck thinks he's gotten Alice pregnant, that Randy is worried about failing trigonometry and that Paul and Kevin are drifting apart.

When Kevin and Paul get on each other's nerves, they try to become best friends with two other boys.

Kevin joins a band, The Electric Shoes, when he is inspired by The Beatles appearing on the Ed Sullivan show.

Kevin enters the race for student-council president, head-to-head with nemesis Becky Slater.

Kevin doesn't want to attend his family's annual Christmas party for the neighborhood because it will only be his parent's friends - all his friends will be away. Jack is busy at work and Norma is busy at college and when several other problems crop up during the party, Norma and Jack argue. When Jack sends Kevin and Wayne to the store, they expect to return home to the worst.

It's lunchtime at McKinley High and the cafeteria is full of life. Chuck spies a potential date. Ricky worries about an assignment he is yet to finish. Wayne tries to win $20 by finding out Maniac's first name. And Kevin is convinced by Winnie to donate blood.

Kevin wants to earn some money to take Winnie out for dinner, so he jumps at the opportunity to paint his sociology teacher's house. When he tries to con some younger students into helping him out, things start to go wrong.

Kevin wants a story that he and Winnie can tell their kids. So, when he is grounded after receiving a speeding ticket, he sneaks out of the house anyway. Kevin, Winnie and friends are off to see The Rolling Stones, who are rumored to be playing at Joe's place, which is out of town. But when they arrive, Joe says he doesn't know who the Rolling Stones are.

When Kevin confronts the school bully, he's driven by his love for Winnie.