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.
After breaking up, Kevin finally sees Winnie again. However, it becomes obvious to him that she has changed and is no longer the same girl that he knew growing up.
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.'
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.
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?
Both Kevin Arnold and Winnie Cooper's schools are having a joint field trip to the local museum. Kevin figures this will be a great chance to spend some time together with Winnie, but things don't turn out as he planned.
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.