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When Santa's Little Helper destroys everything in the house, Homer sends him to obedience school. Just when the dog is about to fail out of obedience school, he bonds with Bart and passes.
Grampa tells Homer he has a half-brother, who he tracks down. He learns his brother is Herbert Powell (Danny DeVito), the head of a car manufacturer in Detroit. Herbert lets Homer design his own car which bankrupts the company.
Selma begs Marge to help her find a husband. When Bart gets in trouble, Homer has to talk to Principal Skinner who he decides to set up with Selma, only he falls for Patty instead.
George gets angry when his girlfriend, Carol, doesn't return his calls and leaves nasty voicemail messages. When he learns she's on vacation, he and Jerry break into her apartment to clear the machine.
Homer gets an illegal cable hookup and Lisa protests the stealing. When Homer's friends come over to watch a boxing match, Lisa's guilt eventually gets to Homer.
Jerry purchases an expensive suede jacket that he wears when he and George go to meet Elaine's father. He ends up ruining the jacket in an attempt to impress her father.
In a flashback, Marge tells the story of how she and Homer met in high school in 1974. The two meet in attention and Homer asks Marge to be his date to prom, but she ends up going with Artie Ziff (Jon Lovitz) instead.
At his aunt's dinner, Jerry makes a comment about hating anyone that grew up with a pony, possibly leading to her death. Kramer and Jerry bet whether he'll add a new level to his apartment.
When the Simpsons go to a sushi bar, Homer decides to try Fugu, a poisonous fish if not cut properly. Homer ends up going to the hospital and told he has 22 hours to live and tries to live his life to the fullest.
After George complains about his girlfriend, Marlene, Jerry convinces George to dump her. After going to pick up some of George's old things from Marlene, he ends up dating her himself.