With Smithers' help, Moe renovates his bar to cater to the "regular" gay crowd, but refuses to tell the clientèle that he's straight. Meanwhile, principal Skinner has a crush on the free-spirited new music teacher.
After visiting a seminar to help boost his confidence around women, Moe employs Homer as his wing man only to find Homer has more luck with the ladies than he does, meanwhile Marge finds her first gray hair.
The family is greeted by folk singer Ewell Freestone when they visit a peach farm, but when Marge goes overboard with peach-inspired dishes, Lisa and Bart try to get rid of the unwanted fruit. Later, Lisa becomes a magician's apprentice to the legendary Great Raymondo who helps her develop her craft, but a schoolgirl crush clouds her judgment when she is coaxed into revealing the Great Raymondo's most famous magic trick to his phony archnemesis. But when the rival magician's act takes a risky turn, the Great Raymondo has one last trick up his sleeve and stages ...
Feeling guilty for getting Mrs. Krabappel suspended after one of his school pranks, Bart helps her escape detention, and Ned Flanders winds up saving her life in the process. When Edna and Ned start dating, he is surprised to learn she's been with many of Springfield's men, including Homer and Aerosmith drummer Joey Kramer.
Homer takes a dangerous dive into an isolated canyon on Candy Peak, but when a crashing boulder traps his arm, he channels Aron Ralston to save himself. In "The Diving Bell and Butterball," the first of three hair-raising Halloween tales, a venomous spider bite leaves Homer paralyzed, but when Lisa discovers Homer's ability to communicate through natural gases, he is able to express his love for Marge. The killer spells continue in "Dial D for Diddly," when Ned Flanders, devout preacher by day, transforms into a cold-blooded vigilante by night. In the final terrifying...
Krusty the Clown is stuck in a rut when the television network pulls his show from the air and his talent agency drops him as a client. But when the Simpsons introduce him to seasoned agent Annie, they are surprised to learn that Annie was Krusty's very first agent. Despite their rocky relationship, Annie is convinced to re-sign Krusty and craft his career comeback. But when Krusty's retro comedy show reboot is deemed a critical success, Krusty must decide to stay with his agent or side with the network executives.
It's the most wonderful time of the year, and the Simpsons flash forward thirty years and find themselves in a tech-savvy, futuristic Springfield. Bart and Lisa have children of their own and decide to spend the holidays as one big family at Homer and Marge's house. Lisa and Bart turn to Homer and Marge for parenting advice and begin to realize that the apple doesn't fall far from the tree.