This is the episode that introduces us to the Krabappel/Skinner pairing! I’ve read criticism of this as artificially putting together two random characters, but it actually really worked for me. Like all good romance stories, it’s a plot that heavily depends on who these two individual people are; there’s so many great jokes that come from Edna being bitter and dirt poor and Skinner being a pedantic dork. But the idea of these two lonely people happening to fall into a relationship out of circumstance and shared recognition is a Simpsons theme going all the way back to the first episode – the sense of people making the best of a bad situation. On a practical level, I love all the jokes of them trying to turn their everyday items into a Romantic Dinner™, but I also love the way their shared experiences and worldview that we’ve seen in countless episodes unites them and gives them a comfortable ground to speak on. Some of my most interesting relationships – romantic, platonic, and professional – have come from coming to the same point from a very different direction, and I love seeing that play out in romance stories, and I love how it plays out here, with the two genuinely building a chemistry out of their differences (“I’m afraid I already swallowed it while you were talking.”). As always, what makes this kind of adult relationship even funnier is watching Bart’s childlike reaction to it; aside from moments that could have been purely cheesy being saved by Bart’s revolted reaction, I enjoy the classic Bart structure of this story, in which he does some big prank, is distressed by the emotional fallout, and tries to make up for it.

The ending of this episode, in which Skinner publicly admits to being a forty-four year old virgin to save his and Edna’s jobs, is very strange, and I have no idea what the show is going for with it. It’s not quite making fun of him for it, and it’s not quite playing it off as nothing. It’s strangely not surprising to find out someone as prissy and lonely as Seymour has never had sex, so it works as a character choice, and it makes sense in the plot, it’s just… what does it mean? One of the shifts in the culture the past decade – especially with this generation of queer people, accepting asexual people as it does – is an increasing indifference to how much or how little sex people have had, and I’ve known quite a few adult virgins indifferent to that fact and widely accepted by their friends; that’s not something that’s made its way up the cultural ladder, with it being assumed that most adults have had and seek out sex, with people who haven’t and don’t being weird antisocial outsiders (notable exception: when Seinfeld had an adult virgin, she was just another person with a particular quirk that caught the group’s attention). That’s present to an extent here, but our sympathy is so strongly with Skinner that it’s hard to figure out how the show expects me to take it.

In retrospect, I can see how season eight is a transitional season, not only showing where the show would eventually go, but where it could have gone. They’re constantly experimenting with new elements of continuity and new aspects of the status quo, in a way that I realise now reflects the occasional shifts in status quo in the first three seasons. It’s like they’re only now straining against the limitations of the attitude that drove the show forward in the Golden Era. The shows that last over a decade – not just your sitcoms like Always Sunny, Modern Family, or Bob’s Burgers but your sitdramas like Law & Order: SVU – are inherently about the status quo, making it a central part of the appeal; Always Sunny is my favourite of these, because the whole joke is that the protagonists are terrible people who learn nothing and will never change, a joke that only gets funnier and funnier as behaviours that seem amusingly childish and self-interested at twenty-eight become monstrously disconnected from reality at forty. It’s not that The Simpsons is too smart (or dumb) to pull that off, it’s that the instincts that push individual episodes forward seem to fight against the very concept of a status quo after a certain point. Always Sunny is always trying to achieve one thing, and part of its growth involves taking on more tools to achieve that. The Simpsons is as voracious with its ambitions as it is with its pop culture obsessions, and not only does it make sense that you would eventually reach a point where you achieved all your old goals and struggle to find more, it makes sense that a status quo would inhibit that search.

Chalkboard Gag: N/A
Couch Gag: The family float in as bubbles that pop.

This episode was written by Rachel Pulido and directed by Susie Dietter, making it a rare Golden Era Simpsons written and directed by a woman. The idea had been bouncing around since the third or fourth season; Pulido took inspiration from the line “His mommy won’t let him out to play,” from “Bart The Lover”. Part of my pleasure in the romance is how great Marcia Wallace and Harry Shearer play off each other.

Love how well the show captures the weirdness of meeting your teacher out of class, and I love about Lisa hiding her vegetarianism to get out of the party. There’s some more great jokes built out of boredom when Bart is forced to babysit Mrs Skinner (and that scene is one of Matt Groening’s favourites). Absolutely love Martin owning Bart so hard (“Now Martin’s scoring off me!”). 

Mrs Krabappel has a candle that looks like Charlie Brown. The movie Skinner, Krabappel, Bart, and Chalmers watch is implied to be The Big Chill. Bart scores a brilliant piece of wordplay on a Star Trek line (“Set your faces to stunned.). The scene of the police trying to force Krabappel, Skinner, and Bart out by playing music is based on tactics used during Operation Just Cause; the song is “Embraceable You” by George and Ira Gershwin. Skinner and Krabappel’s dance was lifted from routines by Orlando Baeza, who was an assistant director on the episode.

Iconic Moments: “I’ve been calling her Crandall!” | “I saw one of the babies and the baby looked at me.” | “Willie hears ya. Willie don’t care.” | “Sex Cauldron?! I thought they shut that place down!”
Biggest Laugh: The last gag here turns out to have been an improv by Dan Castellanetta.