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How Gossip Girl became TV’s coldest teen soap

Leighton Meester and Ed Westwick on Gossip Girl CW
Constance Grady is a senior correspondent on the Culture team for Vox, where since 2016 she has covered books, publishing, gender, celebrity analysis, and theater.

Ten years ago this week, one of the coldest and most nihilistic teen soap operas ever made premiered on The CW.

But you wouldn’t have known that’s what Gossip Girl was going to be from the first episode, or even from the first 13 episodes. It was a series about a group of wealthy private school teenagers living on the Upper East Side, designed to be slick, trashy fun in the vein of its predecessor The OC. It was not meant to be a chilly ode to power and how it makes wealth and sex and love synonymous. But over the course of its six seasons, that’s exactly what it became.

Gossip Girl may have begun as a show full of beautiful, wealthy 20-somethings with perfect hair pretending to be high schoolers in designer uniforms, getting into sexy shenanigans and then crying and group-hugging as they remembered the power of friendship. But by its final seasons, it was about how extreme wealth makes all relationships transactional, and how all romantic relationships are based in exploitation. And the show didn’t so much condemn this nihilism as luxuriate in it: Subliminally, at least, it was as much a part of the Gossip Girl ethos as the lingering close-ups on Blake Lively’s shiny hair and Leighton Meester’s giant tear-filled eyes.

Gossip Girl’s slow transition into nihilism is in large part a result of its decision to embrace its breakout character, Chuck Bass, originally designed as a one-note villain. Chuck gradually became the show’s central character, and his chilly cynicism became its animating perspective. Watching his takeover is a case study in the dangers of letting a single character consume a narrative — and in the deep, subliminal attractions that white male wealth and power can exert over a narrative.

Gossip Girl was originally about human connections. That version of the show didn’t last long.

Blake Lively and Leighton Meester on Gossip Girl
Serena and Blair stage their own photo shoot.

Gossip Girl was originally meant to be about Serena (Blake Lively), her best friend Blair (Leighton Meester), and their fractured relationship; it was also supposed to be about Serena’s burgeoning romance with the hipster Brooklyn outsider Dan (Penn Badgley). Histrionic, overachieving Blair was clearly the most compelling character of the central trio, but the show was aligned along the moral compass offered by friendly, good-natured Serena and righteous, bootstrapping Dan: They provided the lesson at the end of the episode, and the heart.

In one early episode, Blair and Serena argue over which of them should get to appear in a photo shoot for Blair’s fashion designer mother’s brand. The photo shoot is the kind of slick aspirational nonsense that the show built its brand on, but it’s the backdrop for a real emotional problem: Serena, who is effortlessly sparkly and charismatic, wins the chance to appear in the shoot even as she claims that she doesn’t want it. Blair, who desperately wants to be charismatic and sparkly, who wants her mother’s approval, and who feels that this photo shoot will provide her proof of both, is cut out.

“You take everything from me!” Blair screams at Serena. Dan, overhearing, realizes for the first time that Blair is not just a scary high school mean girl but a human being capable of feeling pain, and they share a moment bonding over how awful it feels to constantly strain for the love and attention of your mother without ever being sure that you can reach it.

And then Serena, having successfully begged Blair’s forgiveness, steals all of the clothing from the photo shoot. Together, Serena and Blair run out into the streets of Manhattan in their stolen designer clothes and wrap their arms around each other as they take a string of selfies. “Serena and Blair?” the narrator says in voiceover. “They do besties better than anyone.”

In this earliest iteration, Gossip Girl was a show about friendships and human connection. Dan’s endless judgment and moralizing was often frustrating and self-righteous, but it provided a grounding for all the sexy scandalous hijinks: As fun as the money and the luxury goods were, when Dan provided the central viewpoint of the show, they weren’t the point. The point was being able to authentically connect with someone else, even in the emotionally deadening world of wealth and extreme privilege.

But that version of Gossip Girl was pretty short-lived. It started to fall apart as early as episode seven, when Chuck Bass (Ed Westwick) became one of the most popular characters on the show.

Chuck Bass was originally a villain. Then he became a romantic lead, and everything changed.

Taylor Momsen and Ed Westwick on Gossip Girl
Chuck as villain.

Chuck Bass was originally a minor background character, a villain who epitomized the amoral privilege of the Upper East Side against which Serena struggled and which Dan staunchly opposed.

In the first few episodes, he was clearly meant to be entertaining: He wore flamboyant outfits and was forever swinging a checked scarf around his neck and remarking that it was his “signature,” and he tossed off more bon mots per episode than anyone besides Blair.

But he was also unambiguously a villain. In the pilot, he sexually assaults first Serena and then Dan’s little sister, Jenny. Over the next few episodes, he casually dehumanizes women and anyone who is less wealthy than he is. The Chuck of Gossip Girl’s beginnings was clearly positioned as a love-to-hate character, a polished and witty sociopath it would be easy and fun to root against.

Then came the seventh episode. Blair, reeling from a breakup with her longtime boyfriend, gets drunk and goes out partying with Chuck. Up until now, Blair maintained an ice-princess persona, with her collars all buttoned up to the chin and the intention of losing her virginity to the boy she’d been dating since kindergarten, whom she planned to marry. But in this episode, she gets daring and does a striptease, pulling off the conservative dress her mother zipped her into and dancing in her slip and jewelry. And then she and Chuck hook up — and the fan base watching at home in 2007 went nuts.

“We savored every precious moment of this episode,” Daily Intel announced.

“I just have to write I LOVE Blair and Chuck together,” wrote one fan in the now-defunct Television Without Pity fan forums, to widespread agreement. It was, another opined, “delicious television.”

The prim girl losing her virginity to the bad boy is a classic teen soap trope for a reason: It subverts expectations in a satisfying and sexy way, and it suggests that the good girl is at last rebelling against the expectations placed on her by her restrictive family. Once and for all, she’s making contact with her true self. She’s free. And the bad boy is the one who frees her, which makes him immensely attractive — so Chuck was suddenly, to the confusion of many viewers, wildly appealing.

“It's becoming frustratingly harder and harder to figure out whether he's physically attractive or not,” wrote one fan on the TWOP forums shortly after the seventh episode aired. “When I first saw him, I thought to myself, ‘he could totally play the lovechild of Voldemort and some normal-looking human being,’” another agreed, but “I do feel guilty for ever having thought so.”

The fact that Chuck was an attempted rapist did not, fans insisted, matter all that much for this storyline. That was all in the pilot, after all, and everyone knows that pilots only half-count. In the pilot, Chuck also had a living mother and rode the bus to school, while later episodes established that Chuck’s mother was dead and that he traveled everywhere exclusively by limo. The attempted rapes were like the bus: not really canon.

What went mostly unsaid was that Chuck’s backstory as an attempted rapist actually made his tryst with Blair more compelling than it would have been otherwise. “Are you sure?” he asks her after she kisses him, in a moment that both recalls Chuck’s history of sexual assault and establishes that it matters to him that this particular encounter be consensual.

For the viewer identifying with Blair, the pleasure of this scene comes from the idea that Blair is so special that Chuck does not want to rape her — and by extension, that the women who Chuck did want to rape are worth less than Blair. In real life, no rape victim is worthless, but the “Are you sure” moment depends in large part on a subliminal fallacy, instilled by rape culture, that victims of sexual assault have been degraded somehow. When projected onto the experiences of fictional characters, the idea of being the special woman worthy of being asked for consent offers a heady pleasure, even if it’s illogical.

“Re: Chuck's ‘Are you sure?’ comment...” wrote one fan on the TWOP 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.”

The audience was in love with Chuck, and the writers’ room seemed to be, too. “Just because someone comes into a show as a villain doesn’t mean you’re not going to end up falling in love with them,” showrunner Josh Schwartz told Vulture. “They [Chuck and Blair] came into the show as very different kinds of roles, but the chemistry between them took over.”

Dan and Serena were gradually pushed aside to make room for the story of Chuck and Blair, which came to take over the show. In the second season, the central season-long arc concerned the question of whether Chuck would ever be able to tell Blair that he loved her.

When Chuck became the romantic lead, his worldview took over the show

Leighton Meester and Ed Westwick on Gossip Girl
Chuck as romantic hero, showering Blair with gifts.

It’s not unusual for teen soaps to fall in love with a secondary bad boy character and bump him up to romantic lead, or even for his sensibilities to take over the show. Dawson’s Creek did it with Pacey, and Veronica Mars did it with Logan Echolls.

But traditionally, when the bad boy takes over the show, he has to prove that he has been reformed and establish his good-guy bona fides. Pacey spends a year wooing Joey Potter, building a boat, buying her a wall, and being there for her “in a very Ducky-like fashion” before he gets the girl. Logan Echolls apologizes profusely for his sins, stands by Veronica when she’s solving the mystery of her own rape, and saves her life on multiple occasions.

The result is that the heart of the show doesn’t change significantly as it switches out one male lead for another. Dawson’s Creek is still a nostalgic WASP fantasy about being terrified of teen sex, whether it’s about Pacey or Dawson, and Veronica Mars is still a neo-noir about the vicious scars of adolescence, whether Duncan or Logan is backing up Veronica.

Gossip Girl never quite managed to give Chuck the standard bad-boy-to-romantic-lead redemption arc. Occasionally it would gesture at doing so — one time Chuck faked amnesia and reinvented himself as Henry Prince, the humble Parisian café waiter — but every time it suggested that Chuck was about to turn over a new leaf, he would rapidly return to his old ways instead.

So when Gossip Girl switched its focus from Dan to Chuck, it stopped being a glossy aspirational soap about a group of teens fighting to build authentic connections with each other in a world of obscene privilege. Instead, it became a show that repeatedly suggested there are no true authentic connections, and that all human relationships are at their base transactional and exploitative.

In the new Gossip Girl, romantic relationships were bought and sold

Ed Westwick and Leighton Meester on Gossip Girl
“Look, babe, it’s the hotel I sold you for.”

In the third season of Gossip Girl, Chuck sells Blair to his uncle in exchange for ownership of a hotel. The exchange is explicit and is meant to be sexual (although the uncle backs out of consummating it at the last second), and is set up without Blair’s knowledge or consent.

Within the moral universe of the new Gossip Girl, this event was dramatic, but not morally abhorrent; all relationships, the show suggested, are at their core transactional and exploitative. Every time Chuck made a declaration of love to Blair, it was accompanied by expensive gifts: a jeweled necklace, imported candies, a custom-made couture gown. Essentially, he had bought her. She was his property, and now he was selling her. It was only fair. Within a few episodes, Chuck and Blair were back to declaring their eternal love to each other in romantic scenes drenched in candlelight.

The same thing happened again in the fourth season, in which a drunk Chuck violently grabs a newly engaged Blair, screaming, “You’re mine!” and smashes a window pane over her face, cutting open her cheek. It was unpleasant, the show allowed, but look: Blair was his. He bought her. Only a few episodes later, Blair declares her love for Chuck once again. And when Blair goes through with her wedding (to a prince of Monaco; this show was absurd) only to realize her mistake and wish for a divorce, Chuck buys her freedom. He pays her dowry.

To be clear, I’m not suggesting that the show’s writers and producers intended for late-run Gossip Girl to be read as a sordid and cold story of prostitution and emotional horror. In most of their interviews, they framed the show in general, and Chuck and Blair’s storyline in particular, as an epic, star-crossed romance.

“It was just so beautiful,” said showrunner Stephanie Savage of one Chuck and Blair scene, holding back tears, “the visual of her in her orangey-red gown with her incredible jewels. … And the image of them with the train station in the background as Chuck was about to leave, forever, and turn his back on his identity [this was during the Henry Prince plot line] — for me, that’s everything of the show.”

It seems Savage and her colleagues found the Chuck and Blair storyline to be incredibly romantic, even when he was selling her for a hotel, and they seem to have meant for the audience to feel that way too. But regardless the writers’ intent, the fact remains that the storylines they returned to again and again were at their core storylines of prostitution and degradation. And it’s worth noting that part of what Savage seemed to find romantic about her favorite Chuck and Blair scene was the idea of Blair as an exquisite, expensive object — she rhapsodizes about Blair’s costly Harry Winston jewels — and Chuck as the owner.

Such storylines weren’t even reserved solely for the woman: Blair’s ex-boyfriend Nate spent a string of episodes prostituting himself to a wealthy older woman in order to save his family from financial ruin after his father loses everything. The show framed that particular plot line as naughty and scandalous — but it’s worth noting that it also didn’t frame the relationship as true love. Nate, the show seemed to feel, deserved better than to be the exploited one in his central relationship. But it seems that Blair — and, ultimately, Serena — did not deserve better.

The sole bright spot in the midst of this cold universe in which relationships are bought and sold like real estate came in the form of Blair’s brief season four romance with Dan, which was beloved by most critics and by half of the show’s fan base, and despised by the other half. It was a quippy breeze of a relationship that was explicitly modeled on Katharine Hepburn and Jimmy Stewart in The Philadelphia Story, with Chuck as Cary Grant, and it marked the last hurrah of the first version of Gossip Girl: In a world in which money is so powerful that it makes romantic relationships indistinguishable from prostitution, Dan and Blair were working to create an authentic, meaningful bond outside of the influence of wealth and privilege.

But it couldn’t last. In Gossip Girl’s final episodes, Chuck asks Blair to marry him so that she couldn’t be forced to testify against him in a court of law, because all relationships are transactional. And Dan reveals that he was the titular Gossip Girl all along, obsessively tracking his friends’ doings and secrets and posting them all online (this reveal makes no logical sense and no one can ever make it make sense), but he convinces Serena to marry him anyway, because all relationships are exploitive. Gossip Girl may have begun as a trashy-fun rich-kid soap with heart, but it finished its run as a curdled and soulless treatise about monsters treating each other as property to be bought and used and sold.

In large part, it’s a cautionary tale. Gossip Girl designed Chuck Bass to stand for the attractions and the dangers of the Upper East Side — and then it fell in love with him and let him take over the story. It took a show ostensibly about people struggling for authentic human relationships and turned it into a Liaisons Dangereuses redux — only in this version, the villains turn out to be right about everything, and the people who thought it was possible to authentically care about anyone turn out to be suckers.