Edna Krabappel tells her students to write a paper on World War I, due in three weeks. After class, Edna and Principal Skinner's apple picking date is canceled when Skinner's mother, Agnes, calls him away. At the Simpson household, Bart is distracted from writing his paper. At the end of the three weeks, he still has not started the assignment. The day before the date of submission, he asks Grampa for help. Grampa's story about his WWI experiences as a four-year-old in the trenches is anything but educational, but Bart writes it down anyway and pads it to ten pages using advertisements. Edna rejects his paper and tells Bart he will have to do it correctly after school. As Bart finishes the assignment after school, supervised by Edna herself, he observes Skinner cancel a movie date with Edna when Agnes calls. Bart consoles Edna, and she reluctantly accepts his offer to accompany her to the movie, though she is grateful.
At home, Lisa suggests that Bart nominate Edna for the Teacher of the Year award. Bart's nomination is accepted when the organizers realize that Edna actually managed to teach Bart Simpson (who was believed to be an "urban legend") and survive. When Edna is informed of her Teacher of the Year nomination, she thanks Bart at the ensuing press conference, wondering aloud if she will continue teaching if she does win. Skinner is about to congratulate Edna when Agnes calls again. Bart informs his family that, as nominator, he and his family are going to Orlando, Florida. The family is excited, until they learn the awards show is being held at the EFCOT Center theme park. At the EFCOT Center, Marge and Lisa go on a "World of Tomorrow" ride, "what the people in 1965 thought the world would be like in 1987." Homer and Bart go on an electric car ride, sponsored by "the gasoline producers of America", that tells them that electric cars can not go very fast or far, and "people will think you're gay" if you drive one.
At Springfield Elementary, Skinner is despondent at the thought that Edna could leave the school. Groundskeeper Willie lends Skinner his sports car so he can go to Orlando, where he surprises Edna with a kiss under the fireworks display - until they are interrupted by Agnes, whom Skinner brought along, much to Edna's ire. During preparation for the awards ceremony, Skinner is shocked when he hears that the winner receives enough money to be able to retire. He requests Bart to help him sabotage Edna's chances of winning, though he has to resort to blackmail after Bart initially refuses. At the ceremony, presided over by Little Richard, each finalist must ask their nominating student a question. When Bart is asked what Edna would like to teach the world, he pretends to be illiterate, until Skinner guiltily tells the truth, adding Edna should be Teacher of the Year because "If she can teach me to love, she can teach anyone anything." With one of Little Richard's rings, Skinner asks Edna to marry him, and she agrees. Edna loses the award, but looks forward to marrying Skinner.