Marge pays a visit to Dr. Hibbert when she realizes her hair is falling out. Hibbert concludes there is no physical reason for the sudden hair loss. After listening to a telephone conversation between Marge and her children, the doctor concludes the problem is stress related. Later that day, Marge tells her family about Hibbert’s diagnosis. She also reveals a possible cure: hiring a nanny. Homer agrees that his wife does indeed need help around the house, and the couple begins interviewing nannies. Having seen Mrs. Doubtfire, Homer suspects several elderly British applicants are men in drag, and rejects them outright. He does, however, take a liking to Kearney, a juvenile delinquent. But Marge vetoes the idea. Just when things seem bleakest, help arrives in the form of Shary Bobbins, a young Victorian woman who floats to the Simpsons’ front door holding an umbrella, a la Mary Poppins.

Marge takes an immediate liking to Shary and hires her on the spot. Breaking into song, Shary helps the children clean up Bart’s bedroom. Afterward, Shary and the children enjoy a stroll through a park, where they encounter Groundskeeper Willie (wearing a one-man-band rig), and a kite-flying Mr. Burns. Later that night, Marge tells Homer that Shary is a miracle come true—the children love her, the house is spotless, and all of her hair has grown back. The next day, Shary, believing her work is done, packs her carpet bag and says her good-byes. But the moment she leaves the house, Bart and Homer begin strangling one another. Shary realizes that there’s still more work to be done.

Dealing with the Simpson family for an extended period ultimately takes its emotional toll. One morning, the family finds Shary, drunk and disheveled, on the living room couch. Lisa concludes they have crushed Shary’s gentle spirit. Marge realizes that neither she nor a nanny could ever hope to change her family. With that, Shary sails off on her umbrella as the family waves good-bye. Unseen by the Simpsons, Shary flies too close to a passing jet plane, and is sucked into the engine.