Ep 14. Principal Charming

In The Simpsons season 2 episode 14, titled "Principal Charming," Marge's beloved sister Selma is feeling depressed and lonely, prompting Homer and Marge to try and find her a man. After Homer tries his hand at matchmaking and proves unsuccessful, Marge suggests that Selma ask out the new Springfield Elementary School principal, Seymour Skinner.

Selma agrees, and Skinner, flattered by the attention, accepts. However, upon their first date, Selma realizes that Skinner is not the man for her. Meanwhile, Homer and Marge are convinced that Selma has found her "prince charming" in Skinner, and are disappointed to hear that the pair have broken up.

To make matters worse, Skinner's mother, Agnes, takes it upon herself to try and win Selma back for her son, but Selma is not interested. As the town prepares for the upcoming Founders' Day celebration, Skinner and Selma are paired together to serve as Grand Marshal.

As the day of the parade approaches, Skinner realizes that he still has feelings for Selma and tries to win her back with a grand romantic gesture. However, Selma ultimately chooses her independence over any relationship and decides to remain single.

The episode tackles themes of loneliness, societal pressure to find a partner, and the importance of being true to oneself. It also features memorable moments, including Homer's failed attempts at matchmaking, Skinner's awkward attempts to impress Selma, and the iconic scene where Skinner sings "The Ladies in My Life" to win Selma back.

Overall, "Principal Charming" is a humorous and heartfelt episode that explores relatable themes through the lens of The Simpsons' well-loved characters.