Bart develops a crush on Rainier Wolfcastle's daughter Greta. After hastily deciding he's not ready for love, he dumps her, only to change his mind later. But by then Greta only has eyes for one - Milhouse - and a trip to the set of Rainier's latest movie in Canada isn't enough to win her back.
When Homer steals the Olympic Torch because he hates the way they interrupt his shows once again, he and the family are on a high speed chase that, after Marge gives the torch back to the Olympic administrators (whose helicopter later crashes), leads them to a fair at Springfield Private School. There Principal Skinner steals things for the elementary school, Lisa wants to stay in that school and Bart saves the daughter of Rainier Wolfcastle, Greta, from a gang of bullies. Greta then develops a crush on Bart and invites him to come over to their house sometime. Homer and Marge have to pry Lisa from the school gates, telling her they can't afford to send her and that the only university they will let her attend is in South Carolina. At the Simpsons House, Greta takes Bart's hand, only for Bart thinking she's just playing. Greta then invites him to her school's dance but Bart and Milhouse hear Skinner talking about his bomb at an open mic comedy night and chooses to go there to perform a prank on Skinner and laugh at him, telling Greta he's ill. Bart doesn't realize what his relationship with Greta means until Lisa scolds him for standing her up, so he plans to break up with Greta upon Lisa's advice.
After Bart knows he actually wants to go back with Greta, he finds out she had been dating Milhouse to get back at Bart. This makes Bart to get jealous and tries to win Greta back. He spies them and sees how they enjoy being together. Bart then calls Greta and she tells him her father is going to film a movie in Toronto. He tells his family and they all choose to go to Canada to follow Greta. When they arrive, they visit most of Canada's tourist attractions before they go to the "Paramountie Pictures", the movie studio where Rainer's movie will be filmed. On the movie set, Bart encounters Milhouse, who refuses to let Bart steal Greta away from him, and the pair begin to fight over Greta. They end up on the rink of a curling match match in front of Greta. She is asked to choose between Bart or Milhouse but she turns them both down because Bart's relationship with her is already over and Milhouse isn't masculine enough for her, and plans to put off dating for a few years. Bart and Milhouse then reconcile and realize they are two kids in Toronto with a lot of activities to do, so they choose to join the men's Canadian Olympic basketball team.