Paul and his girlfriend Carla have a falling out. Wanting to make his friend feel better, Kevin offers to set Paul up with Winnie. At first Kevin is happy about the idea, but after awhile, he begins to wonder if he's made a mistake.
On Valentine's Day with Winnie upset at him, Kevin decides to send her a valentine to try and win her over. However his plan goes awry when the valentine is accidentally delivered to Becky Slater, who then thinks that Kevin wants her back.
Kevin is forced to ponder life and death after he's asked to write his obituary for a school assignment. Jack Arnold is facing the annual burden of tax season, and Norma usually does most of the work, but she "faces death" when she loses all the receipts for the year. All the while, astronauts on Apollo 13 also face death in space.
Kevin is persuaded the the baseball coach to try out for the team. But for some reason, even though he's not playing as well as some of the other players he keeps making it to the next cut. Is because he's better than he thought or could it have something to do with the fact that Kevin's dad saved the coach's life when they were in the war together?
Kevin's grades in Mr Collin's Math class are not that good. After talking to Kevin, Mr Collins suggests that he could give him extra lessons to help him on the upcoming test. Kevin seems to be getting better, until one day when Mr Collins fails to show up.
When Paul is voted "Brainiest" on this years Lisa Berlini Poll, he goes through some self esteem problems. That is until Kevin's mom tries to help Paul's confidence and in return Paul develops a crush on Kevin's mom.
When Jack finds dry rot in the house, the mention of moving out gets Kevin worried. But after those worries a squashed, Jack lets it slip out that the Coopers are moving away instead. In order to secure their relationship, Kevin buys Winnie a ring, but Winnie decides that it's best to face the inevitable and just break up. Kevin decides to attend Karen's graduation from high school instead of watching Winnie leave.
With the end of the summer approaching, the Arnolds decide to attend Jack's Labor Day work picnic. When it is learned that Jack was passed over for a promotion that goes to one of his rivals, tensions grow high between him and Kevin, who wants to prove that he is no longer a little kid.
On his first day of the ninth grade, Kevin is bullied out of his locker, humiliated by Becky Slater, scheduled for the wrong class, and meets a new girl who diverts his attention away from thinking of Winnie Cooper who is now at a different school.
With his allowance not going as far as he hopes, Kevin takes a job as a caddy at a local golf course. However, Kevin is dismayed when he finds out that he's caddying for his Dad's boss at NORCOM (who just happens to be playing golf against Jack Arnold, Kevin's Dad).
Kevin receives an I.D. bracelet from Winnie Cooper as a present. The next day, Kevin is assigned to work on a French assignment with an attractive girl named Madeline. However, after working on their project at her house, Kevin rushes out in a panic, leaving Winnie's bracelet behind. Now Kevin has to get the bracelet back in time for his date with Winnie the next night. But how?
Money is tight around the Arnold household, and things don't look so good when the kitchen stove finally dies. Jack goes to NORCOM to ask for a raise, and gets it, as well as a promotion. With the new stove in the kitchen, it seems the Arnold's problems are over, until it becomes clear that Jack won't be back for Thanksgiving Dinner.
When Paul decides to try out for the basketball team, Kevin is convinced that he is just wasting his time. However, when he ends up making the team and his basketball skills improve, it creates a strain in their friendship.
While at the mall, Kevin is surprised to find gym coach Cutlip playing the seasonal job of Santa Claus. When Cutlip realizes that Kevin knows, he gives him preferential treatment in gym class in hopes that Kevin won't tell his secret.