When Did This ‘Simpsons’ Character Become Springfield’s Biggest Horndog?

This week’s episode of The Simpsons, “P.S., I Hate You,” revealed that Marge has secretly been penning angry letters to everyone that pisses her off, including Helen Lovejoy for being a judgemental elitist, and Tim Meadows, for leaving the cast of Saturday Night Live in 2000. She doesn’t send the letters, but finds the act of writing them to be therapeutic. 

It also revealed that one of the show’s oldest characters is far more lecherous than we all assumed. 

After an anonymous thief gets a hold of the letters, Marge becomes the target of a blackmail scheme. The culprit, it turns out (spoilers!) is none other than Shauna Chalmers, daughter of Superintendent Chalmers, aka Gary Chalmers, aka Super Nintendo Chalmers. The aggrieved babysitter, it seems, is hoping to use the money to start a new life with her boyfriend Jimbo Jones (now played by Parks and Recreation’s Mo Collins)

In an effort to retrieve the letters, Marge lies her way into Superintendent Chalmers’ house while Homer searches Shauna’s room. Gary quickly sees through her ruse, but mistakenly concludes that Marge must be hitting on him. “I can’t say the thought hasn’t crossed my mind,” Chalmers thinks to himself. 

Although he knows it’s wrong, he ends up plying Marge with wine, but she escapes while he’s busy changing into a robe that leaves little to the imagination. Chalmers then texts Luann Van Houten, who he’s apparently been hooking up with, despite the fact that she remarried Kirk.

This isn’t the first time this season that the show has given viewers a glimpse at Superintendent Chalmers’ prodigious dating life. In “Desperately Seeking Lisa,” Lisa runs into the school official in Capital City, and learns that he’s been sleeping with both Ms. Hoover and Lunchlady Dora. “Sometimes when grown-ups get bored, they start playing pickleball, or they learn to make sourdough bread, or they book two different romantic getaways with two different women who don’t know about each other, it’s a very common thing,” Chalmers tells Lisa.

This development may come as a surprise to some viewers, considering that Chalmers was originally characterized as a by the book stick-in-the-mud, best known for dryly interrogating Principal Skinner about the plausibility of his steamed hams claims.

So when exactly did Gary Chalmers become Springfield’s biggest ladies man?

His romantic success has been the subject of a number of one-off jokes over the years. In Season Seven’s “Bart the Fink,” Chalmers was briefly seen escorting Agnes Skinner home from a date. Much later, in Season 22, it turned out that Chalmers and Edna Krabappel were “doing it” once she broke up with Skinner, and was looking for a “rebound” from Groundskeeper Willie. And that same season, he claimed to be dating a student’s mother before introducing the school’s new music teacher. 

Chalmers’ relationship to Lunchlady Dora was briefly hinted at last season, but even before that, back in Season 25, he was seen briefly making out with her in a LEGO world that later turned out to be Homer’s cross-promotional dream. 

So hitting on Marge isn’t entirely out of character for Chalmers, but his raging horniness coming at the expense of his own moral compass is a relatively new development.