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Every time I think about Gossip Girl — the glossy, aspirational, slightly wicked teen soap that ruled The CW in 2007 — I ask myself: You mean the show where the romantic lead sold his girlfriend in exchange for a hotel?

In my mind, “Gossip Girl has been rebooted” becomes “The show where the male romantic lead gave his rapist uncle permission to have sex with the male lead’s girlfriend in exchange for the property deed to a hotel has been rebooted.”

“The new version of Gossip Girl has a bonkers premise” becomes “The new version of the show where the male romantic lead sold his girlfriend’s body for a hotel and then manipulated her into thinking it was her idea and then they got married in the very last episode and you were supposed to think it was romantic has a bonkers premise.”

This plot line is emblazoned in my mind, in the spot where knowing how to multiply fractions is probably supposed to be. I can’t escape it. It has baffled me since 2010, when it was introduced during Gossip Girl’s third season: This frothy, sudsy, ridiculous teen soap opera decided to devote multiple episodes to a storyline in which a character sold sexual access to his girlfriend’s body in exchange for real estate — and still expected me to root for the happy couple to end up together. It is wild to imagine how this could possibly have happened!

When Gossip Girl first emerged in the 2000s, it was supposed to be fun and scandalous. Magazines devoted cover stories to the show’s “nasty thrill”; ads for the show featured a cheeky “OMFG.” But where was the fun and scandal in the hotel plot? How did an entire writers’ room come to the conclusion that it could have a character do something so irredeemable, only to somehow bring him back from it? What was the exit strategy? Who thought it was a good idea?

I was watching Gossip Girl in real time when the episode aired. I was 21, and I went over and over the plot in my head. I had been watching Gossip Girl the way I thought it was supposed to be watched — as a silly piece of froth — and in that spirit, I had come to believe that the lead couple was meant for each other. “Is there some way this could work out?” I thought. “Is there any way I could read this as not as bad as it seems?” I was willing to bend over backward to read the plot line as romantic. I just couldn’t seem to find a justification for it. So I came to resent Gossip Girl — and I bore a special hatred for the hotel plot, known in Gossip Girl fandom as the “Indecent Proposal.”

Yet in the decade since the Indecent Proposal played out, I’ve developed a certain grudging respect for it as a skeleton key to an insidious pop culture trope. It has the virtue of being honest. It is a very straightforward way of expressing the value system which underlies all of Gossip Girl, beneath all the high-fashion gloss and perfect hair — and that underlies plenty of other not-so-honest shows of its era, as well.

“I told Chuck I’d take either you or the hotel. He chose to give me you.”

Gossip Girl’s Indecent Proposal played out between lead characters Chuck Bass (Ed Westwick, who would later be accused of sexual assault by four women) and Blair Waldorf (Leighton Meester, 2008 spokesperson for domestic violence awareness). The two made up what was then (and remains) Gossip Girl’s power couple. The shippers called them Chair, and in 2010, there were so many shippers that they went through the Tumblr tag for #Chair and yelled at people posting pictures of actual furniture instead of GIFs of Chuck and Blair kissing.

Chuck and Blair were Gossip Girl’s power couple in part because they were the “bad ones” in the main cast, which made them the most interesting. Blake Lively’s golden-haired Serena van der Woodsen was ostensibly the show’s lead, but she was so well-intentioned, so unwilling to get her hands dirty in the cutthroat politics of Upper East Side high society. Scheming, vicious Blair, with her doll-like face and an infinite array of headbands she wore like crowns, was a far more compelling main character; oily Chuck, who as a teenager bought his own burlesque club and traveled the streets of New York City exclusively by limo, appeared to be Blair’s perfect foil.

The pair spent two seasons deliciously clashing, backstabbing, and plotting their way toward each other, before at last succumbing to their feelings at the end of season two after their high school graduation. In season three, with Blair in college and 18-year-old Chuck taking over his dead father’s real estate empire (look, just go with it), #Chair was at last supposed to be a stable, healthy pair.

(In case you are wondering whether Chuck’s dead father would later be revealed as only fake dead, the answer is: Yes, of course he was only fake dead.)

But then: trouble. Into this garden of Eden came Chuck’s wicked uncle Jack, his father’s longtime business rival. Jack manipulated Chuck into signing over his prized new hotel acquisition via an immensely convoluted scheme involving Chuck’s dead mother. Once the gambit was revealed, Chuck was thrown into despair. How could he win his dead father’s posthumous approval now that he lost the hotel that was supposed to prove that he, too, could be a successful real estate mogul?

(In case you are wondering whether Chuck’s dead mother would later be revealed as only fake dead, the answer is: Over the course of the show, two separate women claimed to be Chuck’s not-actually-dead mother. It still isn’t clear to me whether one or both were lying.)

Jack offers Chuck a deal: He is willing to give back the hotel, he tells his nephew. All Chuck has to do is let Jack sleep with Blair.

Notably, both Chuck and Jack are, within the canon of the show, attempted rapists. Chuck assaulted two girls in Gossip Girl’s pilot, both of whom had to physically fight him off. Chuck himself personally pulled Jack off his beloved stepmother when Jack assaulted her in season two.

The camera cuts away from Chuck and Jack’s meeting as soon as Jack lays out his terms, and viewers are led to assume that Chuck turned him down at once. That’s what each of them tell Blair as soon as they see her.

Jack describes his Indecent Proposal to Blair, assuring her that Chuck would never think of going along with such a thing — he loves Blair too much. Chuck stalks around Blair with an air of stoic tragedy, murmuring dark insinuations about how Jack didn’t ask him for anything he would ever consider giving. Jack corners Blair alone and suggests that it is probably her duty, as Chuck’s loving girlfriend, to make this small sacrifice for him, a sacrifice Chuck himself would never ask her to make.

“Chuck opened his heart to you, and now his future lies in your hands,” Jack says. “Well … not your hands, exactly.”

Blair, in the end, agrees. She draws up a contract, goes up to Jack’s hotel suite, and gets ready to take off her dress. She is nearly in tears as she does so, and tells Jack that Chuck can never find out about what’s about to happen. The implication to the audience that Blair is doing something very dark by selling herself, and that even though she’s only doing it out of love for Chuck, he’ll probably be outraged and hurt if he realizes she cheated on him by sleeping with his uncle. It will become a grand and tragic misunderstanding, like a particularly perverse O. Henry story.

That’s when we learn the big twist. Jack starts laughing and tells Blair to keep her clothes on. He doesn’t really want to sleep with Blair, he tells her. He just wanted to get Chuck to do something so awful that Blair would never forgive him for it.

“I told Chuck I’d take either you or the hotel. He chose to give me you,” Jack explains. “He knew exactly which buttons to have me push. Said you wouldn’t be able to resist stepping in to save him behind his back.”

“Chuck would never do this to me,” Blair says.

She goes back to Chuck and asks him if it’s true that he agreed to Jack’s deal, that he teamed up with Jack to manipulate her into going through with it.

“You went up there on your own,” Chuck says.

(One of the women posing as Chuck’s dead mother was played by Elizabeth Hurley.)

“Are you sure?”

Chuck and Blair first got together in the seventh episode of Gossip Girl’s first season, “Victor/Victrola,” way back in 2007. It was a pivotal episode for both characters, and part of what made the show a sensation. At the AV Club — then at perhaps its peak of TV criticism relevance — “Victor/Victrola” was the episode that gave Gossip Girl its good TV cred.

Up until “Victor/Victrola,” Chuck had been largely a minor one-note villain. He attacked Serena and another girl in the pilot, and caused chaos in the background of other episodes. He made a lot of jokes about his signature scarf and dispensed drugs to lubricate the plot as necessary. He was a classic love-to-hate character, and more than a little bit flat.

In this installment, Chuck purchases the burlesque club Victrola, presenting it to his withholding, not-yet-fake-dead father as a phenomenal investment opportunity. His father, however, turns him down cold. Victrola is just an excuse for Chuck to hang around booze and women, he says. Chuck is crushed. He put a lot of work into his business plan, he replies, and really believes that Victrola can change his father’s business.

Chuck’s father eventually agrees to invest in Victrola, but the period between his disapproval and his change of heart offers us our first glimpse at Chuck’s vulnerability. He is heartbroken, drunk, and lonely; he keeps calling his friends and getting their voicemail. It’s a cue to the audience that this villain is someone we’re meant to begin thinking about sympathizing with.

Meanwhile, Blair has spent the past six episodes reveling in her image as her school’s virgin queen. She wears her collars done up to her chin and casually slut-shames other girls. She seems to have no sense of her own body; when she tries to stand in as a model at a photo shoot to help her fashion designer mother, the photographer dismisses her as too stiff and awkward. She tells everyone who will listen that she plans to lose her virginity to longtime boyfriend Nate Archibald (Chase Crawford), whom she’s been dating since kindergarten.

But as Blair finally accepts in “Victor/Victrola,” Nate doesn’t love her the way that she loves him. So she ends their relationship and then, reeling from the breakup, heads to Victrola to drown her sorrows with Chuck.

At loose ends and ready to establish a new identity for herself, Blair climbs onto Victrola’s burlesque stage, peels off the prudish gown her mother dressed her in, and dances in her slip while Chuck gazes at her in astonishment and admiration. Later that night, as she rides home in Chuck’s limo, she kisses him.

“Are you sure?” Chuck asks. Blair nods, they kiss again, and then you see him start to push down the straps of her slip.

It’s that “are you sure?” moment that launched the ship. Blair loosening her boundaries and at last getting in touch with her sexuality was hot, and Chuck revealing a moment of human frailty when he was rejected by his dad was romantic, but what made the whole internet sit up and take notice of this storyline was the fact that Chuck asked for Blair’s consent.

The character, whose defining trait up until that point was that he was a rapist, wanted to make sure that a sexual encounter was consensual. How exciting. How subversive. How delicious.

“Re: Chuck’s ‘Are you sure?’ comment...” wrote one fan on the now-defunct Television Without Pity forums. “I can see how one could think that was sort of out of character, considering his previous date-rapist ways. Since the first episode, however, it’s been pretty clear to me that Blair is supposed to be the one girl Chuck really admires and has a connection with. That is to say, while he’s generally a huge asshole who wouldn’t care if he took advantage of a girl, with this girl in particular he is concerned about messing anything up. … it makes him a more multi-layered and interesting character, and I’m all for it.”

For the viewer identifying with Blair, the pleasure of this scene comes from the subliminal suggestion that Blair is so special, Chuck does not want to rape her. Hence Blair is worth more than all those other unspecial girls Chuck did want to rape.

The subtext is that those girls weren’t valuable, but Blair was.

Shipping Chair means getting to identify with a character who is better and less rapable than all other women, a character who is meant to be safe from the degradations and depredations otherwise inherent to being a woman within the Gossip Girl universe. That’s why the scene works, and by extension, why Chair works.

Until the Indecent Proposal.

“You’re like one of the Arabians my father used to own: rode hard and put away wet”

Though the Indecent Proposal was shocking, it wasn’t an isolated instance. It fits into two larger patterns spread throughout the entire framework of Gossip Girl.

The first pattern is that Gossip Girl’s two flagship romances — Chair, and the less-beloved ship of Serena and Dan Humphrey (Penn Badgley), who got married in the series finale — are both straightforwardly abusive relationships. And how these relationships are abusive is supposed to be part of what makes them fun to watch.

In the show’s final season, Dan turns out to have been the titular Gossip Girl the whole time, stalking and exposing his classmates due to his obsession with Serena. But Serena decides that this is romantic and marries him anyway.

Chair, meanwhile, is marked both by Blair’s repeated sexual humiliation and by the idea that Chuck owns her.

The courtship phase between Chuck and Blair features multiple instances of Blair attempting to seduce Chuck with lingerie and candles and Chuck brutally rejecting her. The first time they break up, a few weeks after she loses her virginity to him in “Victor/Victrola,” he tells her, “You held a certain fascination when you were beautiful, delicate, and untouched. But now you’re like one of the Arabians my father used to own: rode hard and put away wet. I don’t want you anymore, and I can’t see why anyone else would.”

The pleasure of the ship in those moments comes from the suggestion that Chuck doesn’t really want to be so brutal, but is locked in a power game with Blair. He’ll glance longingly after Blair when she walks away from him in tears, and we’ll understand Chuck is only being so mean to her to win the approval of his father, who told him that human connections made him weak. Or he’ll look troubled, and we’ll realize Chuck only needed to get some of his own back after Blair told him that he was too sleazy for her to want to date him publicly. If he could just wear her down enough to break her pride, we think, he would relent.

The viewer’s knowledge of Chuck’s secret vulnerability combined with his outward cruelty is meant to make it even sweeter and all the more satisfying when Chuck finally succumbs to his feelings for Blair in the season two finale, showers her with expensive gifts, and admits that he loves her. Blair had to work for her victory, which, as the show suggests, is what makes it worth achieving. At last, she’s got her man — and he’s got her, which he signifies by spending money on her. Essentially, Chuck is cementing their emotional connection by buying Blair.

After this grand declaration, Chuck is committed to Blair. He can no longer be cruel to her by rejecting her. So instead, his cruelty toward her takes the form of repeated claims that he owns her, even when they’re not together. When Blair leaves him after the Indecent Proposal, he puts on her what the show calls a “dating fatwa” so that no one else will date her. When Blair eventually gets engaged to someone else, a drunken Chuck muscles her into a corner. As she struggles and protests, he shatters the glass window above her head and a shard of glass slices her cheek open. “You’ll never marry anyone else, Blair,” he tells her. “You’re mine.”

That episode aired in 2011. By then, Gossip Girl was no longer the buzziest show du jour, and its ratings had fallen off a cliff, but this moment was jarring enough that mainstream media covered it. There was a bona fide backlash. The Gossip Girl creative team defended the scene, insisting Chair was not meant to be a depiction of an abusive relationship.

“They have a volatile relationship, they always have,” showrunner Joshua Safran said in an interview with E!, “but I do not believe—or I should say we do not believe—that it is abuse when it’s the two of them.”

(The person Blair gets engaged to is a prince of Monaco. They eventually do get married, and Blair is a princess of Monaco for about six months.)

The second Gossip Girl pattern that the Indecent Proposal fits into is the show’s larger obsession with prostitution. It’s a repeated motif across all six seasons: Chuck repeatedly bonds with other men by hiring them escorts. Minor characters must repeatedly pose as sex workers for one of Blair’s elaborate schemes to work. Blair’s ex-boyfriend Nate has a brief quasi-comic subplot where he sleeps with an older woman in exchange for cash for his family after his father is sent to prison. During their courtship phase, Chuck and Blair make a bet whose terms involve Blair loaning Chuck her beloved maid Dorota, if she loses. (“I don’t want to shine Mr. Chuck’s shoes for a month,” Dorota protests. “Yeah, his shoes if you’re lucky,” Blair replies.)

Consuming sex work and tricking lower-status people into sex work is one of Gossip Girl’s go-to signifiers for soapy, amoral rich-person hijinks. What made the Indecent Proposal shocking within that context is it suggested that even Blair — the ice queen of the Upper East Side — could be vulnerable to such ploys. In the end, her wealth and social status don’t seem to protect her.

They couldn’t protect her, because one of the abusive aspects of the Chair relationship is that it turns Blair into a commodity. Within the value system of Gossip Girl, Chuck can trade Blair for a hotel because he has already bought her with all his expensive gifts.

Chair’s early sexual encounters are repeatedly preceded by scenes where Chuck clasps a jeweled necklace around Blair’s throat. After the Indecent Proposal, Chuck attempts to repeat the same maneuver by putting a diamond necklace around Blair’s neck as a token of his remorse. Eventually, he pays for the dowry that leaves her trapped in a loveless marriage, thus allowing her to get a divorce.

“You thought you could buy me back, just like you thought you could sell me for your hotel,” Blair says. “You bought my divorce and you came to collect your prize.”

(This episode of the show, “The Princess Dowry,” prominently features The Princess Bride’s Wallace Shawn. Wallace Shawn does refer to Blair as a princess bride, but at no point does he say the word “inconceivable,” which is perhaps the saddest oversight Gossip Girl ever made.)

Chuck denies the charge, telling Blair he only wants her to be happy. Yet Blair isn’t exactly wrong when she accuses Chuck of trying to buy her. The fantasy of Chair was always one where Chuck would repeatedly buy Blair. The fact that she was expensive was part of what made it exciting.

“I never thought the worst thing you’d ever do would be to me”

The emotional underpinnings of early Chair are not unusual for teen soap operas, or for romance in general. Pop culture is full of love stories where good women redeem bad men; where the pleasure of a pairing depends upon the specialness of a woman who, by her very nature, makes a predatory man want to not prey on her; where the epic sweep of a romance depends on the idea that some girls are more special, more worthy of not being raped than others. Likewise, it is full of love stories where men demonstrate their love for women through the amount of money they are willing to spend on them.

These stories span decades. The fantasy of being the unrapable girl is at the basis of the hit ’80s film Sixteen Candles. On Gossip Girl’s network sibling The Vampire Diaries, it would become a plot point for Damon and Elena, the show’s flagship couple: Elena was the one woman Damon didn’t want to rape but also the one woman he couldn’t not rape. On Gossip Girl predecessor Dawson’s Creek, there was a plot line where, when Dawson offered to pay for his love interest Joey’s college tuition, she turned him down while tearfully admitting she had lost her virginity to someone else. The implication was that Dawson was trying to buy something no longer for sale, but that it would have been romantic if he had succeeded.

The traditional roadmap of the teen show bad-boy-good-girl love story is that after the good girl redeems the bad boy, usually the redemption sticks. He never stops considering the good girl special. She never descends back into the realm of the rapable girl.

That’s not what happened on Gossip Girl.

“I never thought the worst thing you’d ever do would be to me,” Blair tells Chuck after he sells her to Jack.

Blair would have been safe making that assumption on most shows. But it’s a bad assumption for anyone to make because the underlying reasoning is terrible. It’s an ideology where some women are unrapable precisely because other women are so very rapable, where all women are property but some women are special enough to be property that you don’t sell, where one woman’s specialness depends on the degradation of all other women.

Gossip Girl was a plot-driven (though not particularly good) show with a habit of returning to the same story well repeatedly. That meant it repeated relationship beats — a lot. Over and over again, Chuck would prove that he did consider Blair to be his property, that he did consider her rapable, that he did consider her to be someone who didn’t deserve to control her own body or her sexuality. He would make his opinion of her completely clear, Blair would cry, Chuck would look brooding and regretful, and then they’d be back to having steamy sex a few episodes later. Will Blair’s love stop Chuck from doing something so villainous and beyond the pale? Find out next week when the same exact thing happens again.

The cycle repeated not because it was supposed to be exhausting and nihilistic but because it worked once, so Gossip Girl assumed it would work every time. In the series finale, Chuck and Blair got married.

I don’t think Gossip Girl was more clear-eyed about its value system compared with other teen romances, or that it was savvier or wiser about human nature. Instead, Gossip Girl was clumsy enough to let its underpinnings show, whereas other series like The Vampire Diaries or Dawson’s Creek were skillful enough to give themselves plausible deniability by making their redemption arcs stick.

What Gossip Girl shows is that as the fantasy of the special and unrapable girl iterates and reiterates itself, it loses its magic. Eventually, you’re able to see what lies at the bottom of it: the notion that some women are more valuable than others, that the way a woman’s value is determined is in a marketplace where men buy and sell them. Under this system, you only know you’re valuable enough to win if you can turn a rapist. It’s a fantasy of empowerment based on the subjugation of all women, and it’s the basis of dozens upon dozens of romances.

Gossip Girl proves that it was always a lie.

In the Purity Chronicles, Vox looks back at the sexual and gendered mores of the late ’90s and 2000s, one pop culture phenomenon at a time. Read more here.

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