Principal Charming

Season 2, Episode 27

Worried that Selma is depressed over being single and childless, Marge orders Homer to find her sister a man — but ends up pairing Principal Skinner with Patty (who's celibate here, but later episodes would have her come out as a lesbian) by mistake. Meanwhile, Bart is sentenced to reseed the school's field with Groundskeeper Willie (in his first appearance) after spelling his name out on it with an herbicide he created in science class.