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.
- Canada, Eh?: The family heads to Canada so Bart can win back Greta.Marge: It's so clean and bland. I'm home!
- Did Not Get the Girl: In the end Bart begs Greta to take him back she gives him a flat no, then breaks up with Milhouse.
- Exact Words: When the Simpsons went to Canada, Homer said they'd go "first class". Cut to them on a first class bus.
- Noodle Incident: The family's trip to Europe to retrieve Lisa's lost balloon.
- Oblivious to Love: 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.
- During this same scene with Lisa, we see a flashback to Bart and Greta playing a game of Scrabble. Greta has spelled out numerous words that have to do with romance. Bart then spells out the word "oblivious".
- Old Money: Some prep school students pick on Wolfcastle's daughter because she's New Money.
- Operation: Jealousy: Bart claims Greta is only with Milhouse for this reason, he both agree's and is completely fine with it.
- Sure, Let's Go with That: 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.