Bart falls in love with Rainier Wolfcastle's daughter (who actually has her sights on Milhouse) and the family goes to Canada. Meanwhile, Principal Skinner becomes a stand-up comic.

!! Tropes:

* ExactWords: When the Simpsons went to Canada, Homer said they'd go "first class". Cut to them on a first class ''bus''.
* ObliviousToLove: Greta develop a crush for Bart. But he doesn't realize what his relationship with Greta means until Lisa scolds him for standing her up.
* OldMoney: Some prep school students pick on Wolfcastle's daughter because she's NewMoney.