“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.
Marge enlists Homer's help to find Aunt Selma a husband—and ends up pairing Principal Skinner with Aunt Patty. Meanwhile, Bart gets in trouble for using sodium tetrasulfate (a potent herbicide) to spell his name out in the grass and gets sentenced to reseed the field.
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 starts to go out with a slightly unwilling Patty, much to Selma's increasing chagrin. 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.
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.