The Arnold family and Paul Pfeiffer travel to Ocean City for a little fun in the sun. However, once there, no one really seems to be having any. Paul's allergies flare up, and Wayne and Karen's attitudes are making it nothing like the family trips from long ago. Kevin is still stinging from the news the Winnie Cooper has a new boyfriend, until he meets a cute (but older) girl named Teri.
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.
Just when the Pruitts and their daughter Gina are coming to visit, Kevin gets struck by the most debilitating thing to ever hit a teenager: a pimple! With only a few days until the Pruitts arrive, Kevin resorts to all kinds of methods to get rid of the unsightly blemish.
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.