Kevin joins the school play just to get out of Gym class, while Winnie and Paul seem to take it very seriously. Winnie has problems with her performance, and Kevin unexpectedly helps her during the show.
When Kevin and Paul have a disagreement, they decide to find new best friends. Kevin starts hanging around with Doug Porter while Paul befriends Brady Ryland.
Just when the Pruitts and their daughter Gina are coming to visit, Kevin gets a giant pimple. With only a few days until the Pruitts arrive, Kevin resorts to all kinds of methods to get rid of the unsightly blemish.
New student Larry Beeman turns Kevin on to the wonders of rock and roll. Pretty soon, Kevin purchases his own guitar and is rocking with Larry and his band.
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.'
Grandpa Arnold visits the family and gives Kevin a puppy as a gift, but both Kevin and the pup get caught up in the middle of tensions between Jack Arnold and his father.
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 and his Dad decide to build a tree house in the backyard. However, their father/son bonding is soon derailed when their work gives them a birds-eye view of an attractive female neighbor.
Newly coupled Kevin and Winnie are pressured into attending a notorious make-out party. While at the party, it seems just like any other eighth grade party - until the lights get turned off.
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.
Kevin is persuaded the the baseball coach to try out for the team. Even though he's not playing as well as some of the others he keeps making it to the next cut because his father saved the coach's life when they were in the war together.
Kevin's grades in Mr. Collins' 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. One day, 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.
Karen's 18th birthday is coming up and everybody in the Arnold household is preparing for it but her. But is it because she doesn't want such a pointless traditional or because she's not ready for it?
When Kevin learns that the Coopers are moving away, he buys Winnie a ring, but Winnie decides that it's best to face the inevitable and break up. Kevin decides to attend Karen's graduation from high school instead of watching Winnie leave.
