Kevin enters uncharted waters when he meets an older girl during his summer vacation.

Kevin has trouble in math class when he comes up against a teacher who Kevin thinks is completely unreasonable.

Kevin wants to get to the mall to see a girl he can't stop thinking about, but the only way he can is by begging his brother to drive.

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

Kevin, Paul and Winnie become involved in a production of "Our Town." Trouble begins when Winnie gets stage fright. Kevin thinks he's set because all he has to do is operate the spotlight.

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

When the Arnold family car breaks down and Jack can't fix it, Kevin hopes his father will buy something more fancy.

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

Kevin decides cheating is the only way to get ahead in math class.

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

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.

Trouble begins in the Arnold household when Grandpa Arnold arrives and gives Kevin a dog - a responsibility Jack doesn't think Kevin can handle.

When Carla breaks up with Paul, Kevin sets him up with Winnie to make Carla jealous. But when Paul starts having feelings for Winnie, the friendship is put to the test. To Be Continued...

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.

When Kevin and his dad build a treehouse in the backyard, they discover they get a good view of an attractive neighbor planting her tomatoes. Meanwhile, Doug is in shock after having heard "the talk" from his dad.

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

Pressure is brought to bear on Kevin and Winnie's relationship when they are invited to a notorious make-out party.

When Kevin keeps making the cut for the school baseball team, he worries about whether it is because of his talent or because his dad saved the Coach's life in Korea.

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.

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.

Kevin isn't sure whose side to take when Karen decides to enroll in a liberal college and Jack is dead-set against it.

When Jack begins to complain about dry rot in the house, Kevin begins to think that his father might consider moving. When it is revealed that the Arnolds are staying put and it is the Coopers who are moving out, Kevin buys Winnie a ring as "insurance." Kevin decides to attend Karen's graduation from high school rather than watch Winnie leave.