As Homer drives down a rural road, the Olympic torch in hand, a police helicopter roars into view. It turns out that Homer stole the torch because every four years the Olympics ruin television scheduling, keeping him from his favorite shows. A fed-up Marge grabs the torch and hurls it at the helicopter. The distracted pilot loses control and crashes into a mountain. Later, the family happens upon an annual fair held by the Springfield Preparatory School. Lisa is immediately impressed with everything she sees. Meanwhile, Marge wanders into a bake sale area, where famous chefs Wolfgang Puck and Emeril Lagasse man food stands. A short time later, Bart encounters three snobby bullies harassing Rainier Wolfcastle’s daughter, Greta. Thinking quickly, Bart loads Rice Krispie squares (from the bake sale area)into his sling shot and opens fire. The bullies run off. Greta thanks Bart for his bravery and invites him to visit her house. When Bart realizes who Greta’s father is, he is immediately impressed.

Rainier Wolfcastle drives his Humvee to the Simpson house and brings Bart to his estate. There,Greta and Bart view an Itchy and Scratchy cartoon released on DVD, which features an audio commentary track. Later, Wolfcastle and Greta travel to the Simpson house for dinner. During the meal, Greta reaches under the table and takes Bart’s hand in her own. Bart yanks their hands onto the table and begins to thumb wrestle. But the next time Bart shows up at the Wolfcastle estate, he brings Milhouse with him. Greta, who clearly has a crush on Bart, reacts with unhappiness. Later, Bart overhears Skinner telling Willie about a stand-up comedy act he plans on performing that evening. Seeing a once-in-a-lifetime opportunity at hand, Bart vows to be in the audience…even though he had promised to accompany Greta to a dance. When Skinner takes the stage, Bart heckles him mercilessly. Afterward, Lisa realizes that Bart stood-up Greta. She urges him to be honest about his feelings before Greta gets hurt. Later, when Bart breaks the news, Greta begins sobbing, her heart broken.

When Rainier Wolfcastle learns about the break-up, he promptly kicks Homer off his estate. Later, Bart shows up at Milhouse’s house and realizes his best friend and Greta are now an item. Bart grows jealous…and vows to win Greta back. But when he phones his love, Greta tells him she’s leaving for Toronto, where her father is shooting a movie. Soon after, the Simpsons board a bus headed for Toronto. Marge is immediately impressed by the country, labeling it “clean and bland.” And Homer, intrigued by free health care, immediately puts himself in harm’s way. The family then takes in the sights and sounds of the city, including the CN Tower, the SkyDome and a VFW-style building labeled “Dodgers of Foreign Wars.” Afterward, the Simpsons head for Paramountie Studios, where Wolfcastle is filming his latest movie, “Undercover Nerd.” Bart strides towards Greta, but Milhouse jumps between them. A fight ensues, and the two boys fall onto an icy curling rink. The boys battle it out until they end up at the feet of an irritated Greta. She decides to put off dating all together for at least four years, during which time she’ll act as producer on her father’s movies. However, Bart and Milhouse agree to remain friends.