“Since I'm sure you'd only resent the pity of an eight-year-old niece, I'll simply hope that you're one of the statistically insignificant number of forty-year-old single women who ever find their fair prince.”
Principal Charming is the fourteenth episode of Season 2. It was first broadcast on February 14, 1991. The episode was written by David M. Stern and was directed by Mark Kirkland. The episode contains references to such movies as: Vertigo, The Hunchback of Notre Dame and Gone with the Wind.
Lonely Principal Skinner through a failure to communicate falls for the wrong sister, Patty, making Selma very envious of her sister's new found love.
Patty and Selma visit the wedding of a man that could have easily been Selma's husband, had Patty not gotten in the way. Selma realizes that she needs to find a husband and begs Marge to help her. Marge enlists the help of Homer to seek one out. However, Homer fails to find anyone suitable.
Meanwhile, Bart pulls a big prank by pouring the fictional chemical sodium tetrasulfate onto the grass. Since Bart used it to spell his name, Principal Skinner easily catches him. In the principal's office, Bart is told to call his father, who is currently at Moe's Tavern. After asking for "Homer Sexual," Principal Skinner takes the receiver as Moe verbally assaults who he imagines is his long-time tormentor. Moe gives Homer the phone when he realizes it is Principal Skinner on the other end of the line. Homer goes to the school and decides that Skinner is the perfect man for Selma. He invites the Principal to meet her, but he falls for Patty instead.
Skinner asks an unwilling Patty out on a date and she tries to get out of it by refusing. However as they were going home, Selma tells her that she needs to go on this date because she has not been with a man in 25 years and this would be her best chance to still have a family. On their first date, Patty does not seem impressed with Skinner until he yells at his former student for his lack of promptness. Soon after they go out on more dates, much to Selma's chagrin and she realizes another decent man has just slipped past her.
Meanwhile, Bart takes advantage of the opportunity to get out of his punishment of re-seeding Groundskeeper Willie's grass field and soon takes control of the school. Skinner enlists Bart's help to get Patty to marry him, while Homer fixes a date between Selma and Barney. When Marge learns of it, she disapproves of Barney and demands that Homer finds someone else suitable to date Selma. Homer tries to convince a skeptical Marge that Barney can sober up and be romantic to Selma. When Bart informs them of Skinner's intent to propose to Patty, Selma realizes she can't be picky and accepts the date much to Marge's chagrin.
Skinner takes Patty to the top of the Bell Tower to propose. Following Bart's lead, he has written "Marry Me, Patty" in 40-foot letters using the sodium tetrasulfate that got Bart in trouble. Patty is flattered, but declines. In his grief, Principal Skinner sees what has happened to the school, and takes back control by putting Bart back on his punishment. Patty informs Selma of events, so she breaks up her own date. Things then return to normal as a gleeful Groundskeeper Willie takes pleasure of Bart's misery as he replants the field seed by seed.