Homer suddenly becomes a hair stylist after he beautifully cuts Patty's hair. Meanwhile, Milhouse falls in love with a fifth grader after Lisa 'breaks up' with him.
Lisa attempts to paint a portrait of Patty and Selma, who end up falling asleep. Bart then appears and ruins Lisa's artwork by causing Lisa to paint him into the painting. After Bart and Lisa accidentally toss paint into Patty's hair, Homer uses garden shears to cut the remaining hair, miraculously styling it. Selma demands that Homer style her hair, and he becomes Springfield's most popular hairdresser. Soon, he is styling hair for Helen Lovejoy, Luann Van Houten, Manjula Nahasapeemapetilon and numerous other women in Springfield. However, he discovers that listening to the inane chatter upsets him. He even attempts to commit suicide by drinking a jar of disinfectant. Complaining to Moe and the other barflies, Homer understands that he cannot even look at the men in the bar without seeing everything that the women dislike about them. Eventually, after declaring that he can hear the hair growing around town, Homer styles Marge's hair for a party, and they pretend that Julio created the hairstyle instead. Julio is immediately surrounded by women demanding that he style them, too.
Meanwhile, Milhouse has a life-changing experience after watching Finding Nemo from the beginning. Previously he and Bart only watched the film from "Chapter 2", which takes place after Nemo's mother has passed on. Choosing that, since death can happen to a fish, it can happen to anyone, he plans to live each day as if it were his last. He professes his love for Lisa, even "writing" her a love song (the tune for which is clearly plagiarised from the English folk song "Greensleeves"). Lisa rejects his love, but he manages to impress a fifth-grade girl named Taffy (Kristen Schaal). Taffy and Milhouse begin to date, but
Lisa fears that Taffy is only using him, and begins to spy on them. Her appearance annoys Taffy, who thinks that Milhouse will never love her as he is too obsessed with Lisa, and she leaves. Distraught, Milhouse asks Lisa just how upset she wants him to be in life, Lisa, feeling guilty for really hurting Milhouse kisses him to make him feel better. Milhouse asks if that means Lisa likes him. Not sure what to say at first, Lisa eventually says that what it means is that he should not give up searching for other girls and that life has unexpected things to offer. Milhouse then faints off a cliff but is "saved" by an eagle. Lisa just smiles, glad to see him cheered up.
Lisa does not act much differently to Milhouse than she normally does or mention the events of this episode later on, seemingly implying that her feelings on him eventually went back to how they typically are after this episode.
This episode was the last episode to be shown in the UK of season 22 during August, 2011. The season continued on October 30, when "500 Keys" first aired.