Big Mouth has always been a show easy to overlook, pigeonhole or dismiss out of hand. I confess that I did so myself during its first two seasons on Netflix, after affording the premise a few scant moments of scrutiny. A cast of horny kids, grappling with puberty and the not-so-subtle urgings of their anthropomorphized “hormone monsters”? It reads like it would simply be an excuse for “can you believe they said that?” vulgarity, akin to the early days of South Park, when the novelty of swearing children was both a crutch and 90 percent of the draw.

That’s all the Big Mouth writers would ever need to do, really, to please a certain subset of the TV audience—which is why we should be especially thankful that Big Mouth isn’t content to play to the lowest common denominator. The bawdy humor you’re expecting is there, to be sure, but it’s built around an examination of adolescent development that is often far more poignant and steeped with truth than it has to be. There are moments in almost any episode of Big Mouth that feel achingly familiar to those of us (almost all of us) whose junior high years represented a constant stream of embarrassing, sexually motivated faux pas we’ve spent the years since trying to forget. The show manages to build sympathetic characters out of those disasters, but then re-devotes itself to testing the boundaries of our sympathy.

Never has that last sentence been more true than in Big Mouth’s just-released Valentine’s Day special, “My Furry Valentine.” In its 45-minute runtime, this brilliant piece of writing preys on the audience’s reliance on TV tropes, presenting us with what is essentially one protagonist’s long self-destruction and descent into outright villainy, even as the viewer remains convinced that some kind of absolution must be just over the horizon. It’s such a brazenly pathetic sequence of events that after watching, you realize the episode’s closest parallel might very well be Bryce Dallas Howard in Black Mirror’s “Nosedive.”

Because, in the end, the special is dominated by Andrew Glouberman’s (John Mulaney) devastating fall from grace. Sure, there’s a Nick story here, and a Jay story, and a Jessi/Matthew story—all of whom are still “going through changes,” as Maya Rudolph belts in a beautifully executed cover/tribute to Charles Bradley’s title song. But where each of those stories takes a logical next step in the direction they’ve been progressing, Andrew falls off a cliff. He goes from the likable “classic pervert” we’ve somehow been taught to love to a nigh-unredeemable, physically and emotionally disfigured pariah, rolling around in the rain as his classmates look on in pity and revulsion. It’s genuinely hard to watch, and that’s the whole point: Andrew becomes his worst self in “My Furry Valentine.”

Everything about this image speaks to the person Andrew becomes.

It’s all the more wracking when you realize that the seed of Andrew’s downfall is something we initially took to be a hopeful positive—the fact that he learned Missy was still carrying a torch for him while visiting the The Department of Puberty at the end of Season Two. In any other sitcom, this would be our obvious indicator that Andrew and Missy were due to reunite once more in Season Three. Instead, Big Mouth points out a truth we don’t like to acknowledge: That the illusion of certainty makes us take things for granted. When the question of how someone feels about you is no longer in doubt, trepidation is all too often replaced by a sense of entitlement. In Andrew’s case, this is taken to the extremes of toxic masculinity, and it destroys any fondness Missy might have still be harboring for him.

Unfortunately, it’s not as simple as blaming Andrew’s kangol hat, either—even if Nick posits that “he builds the character out from the hat.” It’s the certainty of Missy’s supposed feelings that imbues Andrew with the unearned confidence of a men’s rights activist, and the gall to proclaim that by the end of Valentine’s Day, she’ll be “eating out of my cool, clammy hands.” His attitude suggests a frightening reality—that this entitlement has been in Andrew’s mind all along, tempered only by his neurotic self-doubt. Remove the doubt, and you’re left with someone truly ugly—a person who doesn’t hesitate to strip every bit of agency from the girl he’s tepidly pursuing. Hence, the immediate panic and cruel retaliation when Missy is friendly toward anyone else, especially the disabled Lars. Even his crude attempts at an apology are undone by possessiveness and a general lack of interest in Missy, the girl he claims to be infatuated with—he doesn’t even remember that she can’t eat chocolate or gummies, thanks to sugar abstinence. He’s revealed to not truly care about Missy at all, beyond “wanting” her as a vague status symbol.

This is all painful enough to watch, especially when Andrew is literally waving dollar bills in front of Missy’s face, asking her what she wants in life, but the brilliance of “My Furry Valentine” is the way it plays with the audience’s expectation that the situation will be repaired. Even after realizing some portion of his caddish behavior, even after questioning whether he’s becoming his own, emotionally abusive father, Andrew can’t manage to rebuild the dike. He arrives at Lola’s party with urgency written on his face, and an audience fully expecting to hear a “we all learned something today” apology and reconciliation. Then he sees Missy with Lars, and that apology never comes. Instead, we get two minutes of ugly, unbearably pathetic meltdown, the likes of which I’ve never seen before in animation. Even with his own hormone monster pleading with him for some kind of sanity, Andrew goes completely and utterly over the edge. He becomes the villain of this story, and although you can certainly pity him, genuine sympathy is much harder. How can you sympathize with the guy commanding a girl who doesn’t like him to “get your coat, we’re fucking going home”? If you were at that party and had an ounce of courage, you’d do everything in your power to stop the girl from leaving with that guy, for her own safety.

Broken, but still blaming everyone but himself.

And that’s the end of “My Furry Valentine.” Andrew has been reduced to a wreck, a shell deformed inside and out, and he still doesn’t realize that no one but him is to blame. As the weight of it sinks in, it becomes clear that there’s going to be no easy way back from this trough in Season Three of Big Mouth. Nick and Andrew have always been presented as this show’s core protagonists, but one of them has lost his way, maybe irretrievably. This tragedy isn’t something that can simply be laughed off when we return to the story—or at least, I certainly hope it can’t be. What Andrew did has to stick, and if he wants his way back into the good graces of anyone, he’s going to have to grapple with the worst aspects of his own gender. It’s going to be a journey you rarely see on TV, and especially within the confines of an animated sitcom.

Kudos to Nick Kroll, John Mulaney, Andrew Goldberg, Mark Levin, Jennifer Flackett, Joe Wengert and everyone else who had the guts to go through with something as devastating and atypical as “My Furry Valentine.” We were already anticipating Season Three of Big Mouth, but Andrew’s story here has turned the premiere of that upcoming season into bonafide appointment viewing.

When The Reclamation of Andrew Glouberman begins, we’ll be there.

Big Mouth’s Valentine’s Day special, “My Furry Valentine,” is now streaming on Netflix.

Jim Vorel is a Paste staff writer. You can follow him on Twitter for more film and TV writing.