A Satanic board game causes other popular board games to come to life, Homer and Marge rescue a possible killer and let him on their boat, and a parody of "Twilight" where Lisa falls for a young vampire.
When Lisa discovers that Marge was also a model student, she tries to find out where everything changed so that she doesn't repeat her mistakes. Meanwhile, a series of chance accidents cause Bart to replace Nelson as school bully.
It's beginning to look a lot like Christmas in Springfield, but while Marge gets in the holiday spirit, it's bah humbug for the rest of the family. Disappointed that she is alone spreading the holiday cheer, Marge sends a letter to Martha Clause to help her save the family Christmas. Martha comes to the rescue and transforms the house into the North Pole chalet Marge has always dreamed of, but when the family is noticeably absent from the perfectly trimmed holiday home, she realizes that it's Homer and the kids who make the holidays special. Meanwhile, the Simpsons ...
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.