It Still Stings: Gossip Girl Dared to Dair, Then Took It Back

Editor’s Note: TV moves on, but we haven’t. In our feature series It Still Stings, we relive emotional TV moments that we just can’t get over. You know the ones, where months, years, or even decades later, it still provokes a reaction? We’re here for you. We rant because we love. Or, once loved. And obviously, when discussing finales in particular, there will be spoilers:

When it comes to the original run of Gossip Girl, there’s a lot that still stings. The finale is what lingers for many viewers, especially the infamously nonsensical unmasking of Gossip Girl (a reveal I’ll ignore for the rest of this piece, because there’s really no use in trying to make it make sense). But the problems with Gossip Girl started a lot earlier, as early as Season 3 or even 2. Season 5, in my estimation, is when the show definitively turned from pretty good to pretty bad, a turn it couldn’t recover from. And yet that season has one delightful bright spot—in fact, one of the strongest storylines of the whole show. I’m referring, of course, to the polarizing love story of Blair Waldorf (Leighton Meester) and Dan Humphrey (Penn Badgley), one of the greatest teen drama romances of all time—while it lasted. And nothing stings more, in my book, than its premature ending.

When many old fans look back at Gossip Girl, they tend to think of the ship nicknamed “Dair” as an unfortunate footnote in the true love story of the show: that of Chuck Bass (Ed Westwick) and Blair—aka “Chair.” And to be sure, Chuck and Blair do have a larger-than-life appeal in the first few seasons, a magnetic bond based on a shared penchant for deliciously twisted schemes. If you haven’t revisited the show since its airing, it’s easy to remember them as obvious soul mates, destined to end up together.

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The problem, of course, is that once Chuck and Blair enter a real relationship, Chuck repeatedly reveals himself to be an emotionally abusive partner, addicted to manipulating and controlling the woman he’s supposed to love. In Season 3, he infamously trades her for a hotel, a breaking point for many viewers; to me, the real point of no return is near the end of Season 4, when he reacts to news of Blair’s engagement by drunkenly punching a glass wall above her, cutting her face in the process. Chuck’s actions throughout that season are textbook examples of domestic violence, a fact pointed out by plenty of critics at the time. (The HBO Max Gossip Girl pilot later had one character refer to the ship as “pre-cancel culture.”)

It’s one thing to ask viewers to root for a toxic relationship; if the chemistry is still strong and the audience wants to forgive a character, they will. Perhaps the bigger problem is just how boring it gets following Chuck and Blair’s constant back-and-forth over 121 episodes. The same goes for Dan and Serena van der Woodsen (Blake Lively), the other original romance of the show, who eventually become step-siblings and later return to each other’s arms more out of inertia and familiarity than any convincing “true love.” (Badgley often looks dead behind the eyes in his later scenes with Lively; he only really comes alive with Meester.)

If I had to pinpoint the period when both of these couples run out of steam, I’d go with Season 4; that’s when Dan and Blair each go through their own heartbreaks and begin to understand that their obsessions might be bad for them. Naturally, that’s when the two become a pair. They organically become unlikely friends through a shared interest in film and art, following an irresistible enemies-to-friends-to-lovers arc (with some more unnecessary digressions, courtesy of Chuck and Prince Louis, mixed in throughout). Their screwball dynamic invites comparisons to Harry and Sally, evoked by conscious references like the split-screen scene when they watch Rosemary’s Baby together over the phone. They’ve also been compared to Dawson’s Creek’s Joey Potter and Pacey Witter, a similarly combative-but-adorable teen relationship that came together naturally after the main pairings got stale.

Blair’s kinky sex life with Chuck may be more immediately memorable than her sex life with Dan, but they still share a powerful physical chemistry—one based on an initial mutual irritation that slowly mutates into an intimacy that startles them both. Even in their early appearances together, Blair often seems to be standing near Dan, eager for an excuse to smack him (or, later, wrestle him at a work event). The early establishment of their dynamic is perfectly summarized by their two main scenes together in Season 1. In “Bad News Blair,” only four episodes in, Dan finds Blair upset in the hallway and opens up to her about the mother he wishes he was brave enough to confront. In the finale 14 episodes later, Dan and Blair hatch their first scheme together to run Georgina Sparks out of town.

Those early scenes are emblematic of Dan and Blair’s innate understanding of each other; they challenge and call each other out when necessary, whereas Serena and Chuck only encourage them to be their most immature selves. During the slow burn of growing sexual tension in Season 4, Blair points out, “When was the last time you wrote anything? Scribbling ‘D loves S’ all over your journal every night doesn’t count.” An episode later, Dan says, “You do know that ‘powerful woman’ is not actually a career, right?” to which she replies, “And neither is ‘Serena van der Woodsen,’ but ten bucks says that you’ll miss your interview waiting for her yet again.” Dan fires right back, “Ten bucks whatever harebrained scheme you’re cooking up blows up in your face, as per usual.” Both, of course, end up owing each other ten bucks.

Dan isn’t always flailing to keep up, in either witty repartee or in manipulation—in fact, he successfully pulls off vengeance against Blair a number of times, and has his own frequent lapses in ethics. But more importantly, Dan doesn’t need to be on equal footing with Blair when it comes to dastardly plots. While all Chuck and Blair really share is a love of “the game,” Dan comes to understand better than anyone else who Blair actually is as a person, seeing her at her most ambitious and her most vulnerable. Chuck may appreciate her gift for scheming, but Dan pushes her to be honest about who she is at her core, and in return, Blair pushes Dan to confront and ultimately embrace his guilty enjoyment of the elitist Upper East Side milieu he now occupies. “You pretend not to be like us, but you are, to the bone,” she insists at the end of Season 2.

The relationship that finally flourishes in Season 5 isn’t explosive the way Chuck and Blair are, but it’s just as charming and far more aspirational. The stunning openness on Meester’s face when she first tells Dan, “I told Chuck he doesn’t have my heart anymore. I realized it belongs to someone else” shows a purity and unconditional warmth she’s never allowed herself to express to him before; it’s all the more triumphant because of how long it took to get to this moment, as evidenced by her newfound comfort using “Dan” instead of “Humphrey.” It’s the most swoon-worthy moment since Chuck finally told Blair he loved her at the end of Season 2. It’s also followed by a beautiful (if temporary) happily-ever-after moment a couple episodes later, when Dan takes Blair outside the MoMA to live out her princess fantasy one last time, swarmed by adoring fans as she dons a cheap tiara.

That scene, for fans like myself, works pretty well as an alternate ending. In canon, unfortunately, Season 5 ends with Blair inevitably going back to Chuck, a deeply contrived and massively disappointing reversion to “the original plan” akin to Ted and Robin’s inexplicable reconciliation in the How I Met Your Mother finale. (And the less said about their scenes together in Season 6, the better.) In these shows, there’s seemingly a law that whoever locks eyes first is endgame. Dawson’s Creek, for all its faults, was mature enough to move past its original plan, sticking with what actually made sense for the characters six seasons later. Why couldn’t Gossip Girl?

Ben Rosenstock is a New York City-based writer and critic whose work has appeared in Vulture, Slate, and TIME, among other publications. You can follow his TV musings on Twitter @brosenstock18.

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