Kevin's continuing longing for Winnie has caused him to become frustrated with being alone. And it's not helping that his best friend, Paul, now has Carla. When Kevin reaches his breaking point, he ends up asking Becky Slater to go steady, even though it's just to make Winnie jealous.
Kevin feels that his piano lessons with Mrs Carples aren't doing him any good. While most people are quick to commend Mrs Carples' student Ronald Hirschmuller, Mrs Carples still feels that Kevin has got musical potential, if he'd just apply himself more to practicing.
When Kevin sees that Paul is being humiliated at basketball during physical education class, he decides to go to Coach Cutlip to complain about how he thinks teams are being unfairly picked. Cutlip then decides to teach Kevin a lesson about fairness by making him a team captain.
Kevin along with kids from his school plan to schedule a walkout to protest the Vietnam War. However, when the assistant principal, Mr. Diperna, finds out about the planned walkout, he threatens to suspend all who participate.
Now that Kevin is back together with Winnie Cooper (after hurting Becky Slater's feelings), Kevin thinks his problems are behind them. Until he remembers how he ridiculed his friends (including Winnie!)behind their backs to impress Becky, who doesn't seem too happy to have been dumped.
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.
Paul Pfeiffer and Kevin Arnold's birthdays are just days apart, and the two friends have usually always celebrated together. But this year, upon turning 13 Paul(as per Jewish Tradition), will become a man. The only problem is that Paul's Bar Mitzvah happens to take place on the same day as Kevin's Birthday!
The gym class is engaging in square-dancing, and Kevin is paired up with Margaret Farquhar, the strangest girl in 7th grade. While Margaret enjoys spending time with Kevin, her presence makes Kevin wary of his junior-high image.
As the end of school approaches, Kevins looks forward to spending the summer with Paul and Winnie. However his wonderful summer is spoiled when Paul tells hims that he'll be going his parent's cabin until Labor Day and Winnie seems to be avoiding him.
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.