When the TV breaks, Marge tells how she and Homer first met in high school and went to the prom, but not together. Marge asks Homer to find a good man for Selma, but he has difficulty. Homer meets Principal Skinner and learns that he's single. Homer invites Skinner for dinner to meet Selma. Homer accidentally introduces Patty.
Skinner falls in love instantly.
When they start dating, Selma becomes even more desparate. Homer finds that he has a rich brother called Herb, but Herb's car company, Powell Motors, is losing to Japanese companies, and Herb relies on Homer to save his business by designing a car. Homer's new shoes and Bart puts the dog in Canine College, but he makes no progress. When Santa's Little Helper destroys the family quilt and eats Homer's cookie, Homer says it's time for him to go. Homer goes on a weight-loss diet and Marge pursues her artistic talent.