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:

* CanadaEh: The family heads to Canada so Bart can win back Greta.
-->'''Marge:''' It's so clean and bland. I'm ''home''!
* DidNotGetTheGirl: In the end Bart begs Greta to take him back she gives him a flat no, then breaks up with Milhouse.
* ExactWords: When the Simpsons went to Canada, Homer said they'd go "first class". Cut to them on a first class ''bus''.
* NoodleIncident: The family's trip to Europe to retrieve Lisa's lost balloon.
* 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.
* OperationJealousy: Bart claims Greta is only with Milhouse for this reason, he both agree's and is completely fine with it.
* SureLetsGoWithThat: Greta thinks Bart's joking when he says his mattress is filled with hay and he decides to let her think she got it right.