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.
Marge gets depressed when the rest of the family does not get into the holiday spirit, and she writes a letter, hoping to get some help; Mr. Burns and Moe's new friend delay the Simpsons as they attempt to travel to Hawaii for the holiday.
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 ...
When Krabbapple gets suspended and put into detention after hurting Bart, Bart tries to break her out, but it ends that Flanders is the one that saves her life. But soon, Ned figures out that Edna has also dated other men such as Homer, Skinner Comic Book Guy and Aerosmith drummer Joey Kramer.