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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.

When Kevin starts having car trouble, he asks Alice Pedermier to try and get him a good deal on a new car at her dad's dealership. However, when she dumps his friend, Chuck, Kevin has second thoughts about accepting anything from her.

Karen doesn't communicate with her parents anymore. It's made worse when she brings home a new boyfriend. Kevin takes an immediate dislike to Louis.

As summer begins, Kevin is dismayed that almost all the fun of previous summers is gone. All his friends are working summer jobs, and his Dad wants him to do the same. Feeling that the world has turned on him, Kevin and Paul head back up to the Lake, where Kevin hopes to find a girl he met at the Lake a year earlier.

Kevin and Paul have usually celebrated their birthdays together. But when Paul turns 13 and his Bar Mitzvah is about to take place, the convention is endangered.

To get closer to his sister, Kevin agrees to run errands for her before school. He soon discovers that she is skipping school to hang out with her friends at the "rock".

A misunderstanding at a burger joint causes Winnie to give Kevin the cold shoulder. Kevin tries to patch things up, while remembering the moments that brought Winnie both closer and away from him.

Buster, the Arnold Family dog, doesn't seem to be behaving himself lately. When it seems that the only course of action is to have him 'fixed,' the family has to make an important decision.

Kevin and his friends try to sneak in to see Carnal Knowledge. Meanwhile, Paul ends up having sex with a friend of the family, leaving him feeling confused.

Kevin and Wayne try to convince Jack to buy a color television for Christmas. Meanwhile Kevin tries to find the perfect present for Winnie after she unexpectedly gives him a present.

With the holidays approaching, the Arnolds get ready to host their annual Christmas party. However, this year's party will become memorable ... for all the wrong reasons.

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.

Kevin feels that his piano lessons with Mrs. Carples aren't doing him any good. But Mrs. Carples feels that Kevin has got musical potential and sets him up against her best student, Ronald Hirschmuller.

Following a trip to the dentist, Kevin finds out that he needs to have a cavity filled. He puts off going back in fear that he will look like a coward in front of the lovely dental hygienist, who is always complimenting him on his courage.

Kevin asks Lisa Berlini to a dance but she dumps him. Dejected by Lisa's rejection, Kevin finds himself asking Winnie to the dance, but he finds out she is going with her new boyfriend. In retaliation, Kevin tries to make Winnie jealous.

On his first day of high school, Kevin quickly realizes that it is not quite the same as junior high where he knew everyone and was the high man on the totem pole. He is followed by an annoying classmate, bullied by Wayne, and picked on by an egotistical teacher.

After getting dumped by Winnie, Kevin begins to doubt whether it is really over between them. In hopes of getting her back, he convinces Paul to throw a party and invite Winnie. But things don't go as planned.

For Jack's 43rd birthday, Norma decides to try and repair his relationship with Karen by having them meet at a restaurant. Her plan begins to backfire when Jack continues to begrudge Karen's live-in boyfriend Michael.

Kevin wants to ask Susan Fisher to the next school dance, but can't find the courage. Wanting to help him out, his lab partner Linda offers to go with him, 'as friends.'

When Kevin develops a crush on the new Swedish exchange student, he asks Winnie to help fix him up on a date with her. In return, Winnie asks Kevin to fix her up with a new student that is in one of his classes. Things get interesting when they are all forced to double date to the spring dance.

Kevin and his classmates take a bus trip to the planetarium to witness the solar eclipse. On the trip, Kevin and Winnie have a fight after he calls her "too perfect" while Chuck gets locked in a restroom, leaving him behind.

Kevin is forced to ponder life and death after he's asked to write his obituary for a school assignment. Jack is facing tax season and Norma usually does most of the work, but she loses all the receipts for the year.

With Winnie still upset at him, Kevin tries to get back on good terms with her by confronting Eddie Pinetti, the school bully, for going into her locker. This plan backfires when he realizes that Winnie is now seeing Eddie.

The Arnold men embark on their tri-annual three-day fishing trip. While on the trip, it quickly becomes evident that Kevin and Wayne have outgrown the whole camping experience.

Denise and Frank seem to be made for each other, until Denise turns her eye to Kevin because he understands poetry. Although she breaks up with Frank and kisses Kevin, Kev thinks it would be better if she went back to Frank because they are a perfect match.