Embraceable You
composed by George Gershwin; written by Ira Gershwin

Seymour Skinner and Edna Krabappel strike up a conversation at a party and take a romantic interest in each other. They try to keep their affair a secret, but Bart sees them kiss. The following day the couple hears Bart telling his classmates about it and silences him by deleting his permanent records. Bart becomes their go-between for exchanging love notes, but he gets tired of that and exposes Skinner and Krapappel in the janitor's closet locked in a passionate embrace. The word spreads all over town and Superintendent Chalmers gives Skinner an ultimatum. Either end the relationship or face dismissal. Skinner admits that he is in fact a virgin and the matter is cleared up.

In the episode, Grampa's new girlfriend at the Retirement Castle passes away and leaves him with $106,000. He heads for a casino to spend the money, but is stopped by Homer, so he decides to spend the inheritance money on renovating the retirement home instead.