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.

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 thinks his mother is being over-protective when she tries to stop him from playing tackle football after school.

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

When Paul is voted "brainiest" in Lisa Berlini's latest poll, he goes through a crisis but is helped through it by Mrs. Arnold - who he also develops a crush on.

News of a 10th-grade girls' slumber party has Kevin and his friends traveling across the city, believing they'll be invited in if they bring beer.

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.

Paul's sister Debbie needs someone to take her to a cotillion and Kevin is guilted into the task. Meanwhile, Paul, Doug and Randy go to the football game to watch cheerleader Donna Delgado.

Kevin discovers a soft-spot inside Cutlip when he sees him playing Santa Clause at a local mall.

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

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.

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.

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 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 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.

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.