Saturday, June 15, 2024

The Tragedy of Blair Waldorf, Part 2

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Hello friends, and welcome back to my obsessive Watsonian analysis of Blair Waldorf. For Part 1, click here.

We’ll pick up right where we left off last time.  To follow this analysis, reading part 1 is highly recommended. I should also do a quick reminder that these pieces cover Blair’s character seasons 1-5, and will not go into the final season. Why do that to myself?

Now, where were we?

The Ruins of a Toxic Love

As a refresher, Chuck sold Blair for a hotel, and Blair broke up with him. He insisted on getting Blair back and eventually gave her an ultimatum. Either she went back to him or it was over between them forever (it likely wouldn’t have been over). Blair runs to him, but is late, and Chuck immediately sleeps with Jenny Humphrey.

Their getting back together is short-lived, as Blair finds out about Jenny. In the immediate aftermath of all this, Blair decides to go to Paris with Serena to disconnect. Chuck, for his part, settles on Prague instead. There, he is mugged and refuses to give up an engagement ring that would have been Blair’s, so he gets shot. And, ugh, restrain me guys, I can’t stop thinking about Doylist perspectives because this is the last scene of season three. But whatever, I’m cool. Watson it is.

Blair sans Chuck

Who is Blair Waldorf…? Without Chuck Bass?

Chuck was all-encompassing for her. So much so that other characters began to see them as a pack.

Dan: “If there’s a pair meant for one another, you know, it’s you two”.
Blair: “You’re absolutely right. ‘Chuck and Blair, Blair and Chuck’… who else could love me after what I’ve become?”

That is a lot to unpack.

Her identity is so intertwined with Chuck’s that she can’t even find outrage for herself after being sold for a hotel. She feels guilty and dirty. She breaks up with him because she doesn’t like herself when she’s with him. She is afraid of the lengths she will go to for him. But she’s not afraid of him. She is not mad at him. This speaks volumes of the way Blair perceives herself. She is the one who is terrible. She and Chuck belong together, because “who else could love her”?

Realizing “they belong together” isn’t a thrilling moment of love, but a devastating blow for her.


Blair: “Everything you said last night was true. We do belong together. We’re both sick and twisted. If you think about it, we’re incredibly fortunate to have even found each other. […] We’ve both hit rock bottom, Chuck, but we’ve hit it together. At least we won’t be lonely in hell.”

At the start of this scene, Chuck offers a necklace and she lets him put it on her. The scene mirrors one from season 1, episode 8, where Blair waits all night for Nate. Instead, Chuck is the only one who goes to ger, and gives her a present:

In both, Chuck takes advantage of Blair’s vulnerable state and lays claim to her through a material thing. The idea that informs both moments is “no one else loves you, you might as well take this love”. This is an idea that has a huge influence on Blair, who feels unloved a lot of the time, and it will come up again in her relationships with Louis and Dan.

What does she do when she loses that? She retracts her steps. It is like Blair asks herself “Who was I before this?” The problem is that before she was the girl obsessed with Chuck, she was the girl obsessed with Nate. Throughout season four and halfway through five, Blair ping-pongs between these two, interspersed with attempts to find herself—her true self.

Irreparable Tangles

Opening season four, Chuck is alive and recuperating with the help of a woman named Eva, while Blair meets a mystery man while out and about in Paris. Her suspicions turn out to be true, Louis is a prince of Monaco, because of course, he is.

While in Paris, Blair discovers Chuck has decided to give it all up, including his name. Because Chuck is a tad dramatic, too, did I forget to mention that? Anyway, she goes to stop him, because even though she tells herself (and him) that she doesn’t love him anymore, she is yet unable to untie herself from him.

That Chuck made a show of giving it all up for having lost Blair is a huge deal as well. Among other things, it sends a message that he regrets selling her for the hotel, given it is one of the things he’d be renouncing. I’m not here to analyze Chuck thoroughly, but I’d be willing to bet all of it was just that, a show, all meant for Blair.

Chuck: “I destroyed the only thing I ever loved.”
Blair: “I don’t love you anymore. But it takes more than even you to destroy Blair Waldorf.”
Chuck: “Your world would be easier if I didn’t come back.”
Blair: “That is true. But it wouldn’t be my world without you in it.”

Chuck does come back to New York, and soon they fall into yet another destructive cycle of manipulation and later a hateful sexual relationship until finally, they go back to admitting they love each other. When Blair discovers she would have to give up her opportunities to make it on her own, she puts it off.

“As long as I’m with you I’m Hillary in the White House and I wanna be Hillary, Secretary of State but… with better hair.”

She finds she doesn’t want to be “Chuck Bass’s Girlfriend”. She wants to settle into herself before they get back together. The only problem with her logic is that Chuck becomes the end goal, in a way.

“I have to be Blair Waldorf before I can be Chuck Bass’s Girlfriend.”

Blair, the Career Woman

Blair struggles with finding a career choice that suits her. She doesn’t want to be defined by her mother, so she resists her own urges. Ultimately, she does choose Fashion, but she strives to make her own way instead of using Eleanor’s influence.

She secures an internship at W Magazine through her own means and proceeds to overwork herself to the point of insanity.

It would be easy to assume Blair, an heiress who expects to marry into money, would be blasé about getting career opportunities. All her family and friends have connections and they can get her an opportunity. But Blair’s mom is a career woman who sets an example of effort and hard work. Blair’s need for validation stems, in its origins, from Eleanor.

Thus, Blair has always felt the need to prove herself. If she had the social skill she could cruise it, like Serena, who is only worried about her working future while she’s having an existential crisis. If she really didn’t care, she could just… stop. Blair doesn’t need to work to make a living. She wants to.

She is also someone who wants to excel at everything immediately and gets frustrated if she doesn’t. Frustration leads to scheming to get what she wants anyway. However, it is different at W. Through experience Blair has learned that scheming can lead to catastrophic results (remember Yale?). Blair opts to work hard instead of plot, to ask for help instead of hold on to her pride. But there is still one problem.

“I thought that if I could be the Blair Waldorf that I want to be a little sooner, that maybe I could return to Chuck before he fell for someone else.”

The goal of becoming Blair Waldorf sans anyone was tainted from the start because in the back of her mind, it was a race toward Chuck. As soon as Blair’s career became a competition with another woman (older, a businesswoman), it was doomed.

Louis: NATE 2.0, The Upgrade

It may seem like Louis is a new, completely different guy than Nate. But regarding Blair’s psyche and perception of herself, Louis is simply an upgrade from Nate.

As she is disappointed by Chuck once again, Blair reverts. She spent most of her adolescence in love with Nate. Except, was she? As discussed briefly in the past article, Nate has pedigree; he is from the Vanderbilt line. Going to a debutante ball on his arm is instant acceptance into the most elitist New York society.

Blair was not in love with Nate, she was in love with class and status. (Later, Nate came to mean safety and childhood, but that’s beside the point now.) And who represents class and status more than a European prince?

Take that and mix it in with the huge boost to Blair’s bruised self-esteem post-Chuck. Louis noticed her in Paris long before he talked to her. Later he flew to New York to seek her out even when his position forbade him from courting her. It’s something out of a damn storybook. Blair eats it up.

At this point, however, Blair is not a hundred percent convinced she’s this girl obsessed with class and status anymore. She’s not convinced she’s just the girl Chuck loves, either. But who is she, if she’s not one of the two? Her entire relationship with Louis is corrupted and complicated by this internal conflict.

As soon as Louis comes int the picture, suddenly Chuck is desperate to get Blair back, where a handful of episodes ago he was pursuing another woman.

“Match, Blair. You’ve proved you can score a prince, okay? I admit you made me jealous. Let’s go back to my place so you can collect your prize.”

I… fail to say how anyone ever found this romantic. Blair, now caught up in a modern fairytale beyond her most ambitious fantasies, is having none of it at the time. Louis soon proposes to her, and she says yes. Then right after that, she goes to Chuck.

Blair has just become engaged to a literal prince. She is to be a princess now. Chuck has just spewed the quote above, in front of the Royal Family of Monaco, publicly embarrassing her. Still, her first thought is of Chuck’s feelings when he finds out

This isn’t romantic as much as it is worrying. It is a red flag for her self-respect and her new engagement; she prioritizes his feelings over her own happiness.

It is at the hotel Chuck sold Blair for, The Empire, that their abusive relationship escalates into physical violence.

Chuck: “I need you, Blair. Like I never have before. Everything I believed about my father, everything I thought I wanted to be, what I needed to be for him was based on lies. The only thing that’s ever been real is me and you, and you know that.”
Blair: “Louis asked me to marry him”.
Chuck: “You’ll never marry anyone else, you’re mine”

He then tries to force herself on her and when she fights back, he punches a windowpane beside her head, hurting her in the process.

I remember distinctly, as I was watching this scene I thought “finally, this will be the one that breaks the Chuck Bass spell for the fans”. But nope. In the wake of this episode, I remember reading a Tumblr post that read something like: “Oh, did you see what a beautiful, dainty scar he left on her? Swoon”. Well, at least it will break the spell for Blair, right?


Louis, you dumb vengeful vampire

Let’s talk about Louis for a second. He is a hopeless romantic—and a bit intense in that department, immediately proposing to Blair—and deeply insecure. He is also a bit slow on the uptake, failing to read obvious signs and social cues, presumably because he is smitten with Blair.  In a way, he too is in love with the idea of this fairytale where “the prince marries the commoner” just as much as, if not more, than Blair.

Blair was never going to stay with Louis. Much like Nate, he was always an illusion. And though he seems good-natured, even a bit of a pushover, he is nothing like well-meaning Nate, in the end.

Blair and Chuck circle around each other for a while after the windowpane debacle. After some back and forth, Blair decides she wants Chuck. He decides to be the martyr, once again denying her when she comes to him. But they do sleep together, and when Blair becomes pregnant, there is a chance it might be Chuck’s. This brings them together again, though the baby turns out to be Louis’s. Chuck and Blair run away together but get into a huge car accident.

When Chuck’s life is in peril, Blair makes a promise to God that she’ll keep her vow to Louis if Chuck lives. That is how Blair ends up marrying the prince of Monaco, after all. Of course, Louis finds out (very publicly) that Blair’s declared her undying love for Chuck, and chooses to forgive her for appearance’s sake.

“Our marriage is all for show. And you’re going to put on the best damn show anyone ever has”.

Ah, Louis ends up being an abusive ding-dong after all. We should have all seen that coming. So, after diving headfirst into her modern fairytale, Blair ends up escaping it in a getaway car. And who is in there with her?

Dan, the Unlikeliest Choice

If you ask me, the development of Dan and Blair began all the way back in season one, episode four. After Blair finds out she has been replaced by Serena in a photoshoot, she is consoled by Dan.

“Normally I wouldn’t be this close to you without a tetanus shot.”


At this point, it has been established that Blair thinks very lowly of Dan (or “Lonely Boy”, as Gossip Girl calls him). And Dan has an equally unkind opinion about her. For the first time, Dan realizes there is more than one shade to Blair and decides to level with her. Blair, for her part, lets down her guard in front of him for the first time.

Throughout the next five seasons, Blair and Dan develop a relationship. They start with tolerance, move into mutual respect which evolves into friendship and ultimately, romance. There are many who feel like the romantic relationship between the two felt forced and, but I’d say there’s subjectivity and bias laced into that, because “Dair”, had a fanbase from the start. I myself gravitated towards them, if you couldn’t already tell—I was even one of the O.G. theorizers.

However, I am here today to argue that their relationship, or more accurately, the circumstances of their relationship, were one of the major catalysts for “The Tragedy” that became of Blair Waldorf.

The Real Star-Crossed Lovers

One of the thematic through-lines of GG, at least in the first few seasons, was the clashing of two worlds: the excess of Manhattan’s Upper East Side and working-class Brooklyn. Originally, these two sides were represented by Serena and Dan, respectively. Though there were some issues with the joining of their worlds, there never really was much conflict between them that stemmed from that specifically.

None of the prejudice and classism that permeates Serena’s world was in her regarding Dan. He made an exception for Serena for scathing prejudice of the filthy rich. While we’re not here to talk about Dan and Serena’s relationship, one of the most crucial aspects of it is Dan’s idealization of her.

The way Dan sees Serena and Blair is a textbook example of the Madonna/Whore Complex. Serena is the exception, the one good thing about the Upper East Side; she always has good intentions, she’s always the victim. Meanwhile…

“[Blair] is everything I hate about the Upper East Side distilled into one 95-pound, doe-eyed, bonmot-tossing, label-whoring package of girly evil”

In terms of the clashing of opposing worlds, Dan and Blair had a much more complex story to tell. The process of them becoming friends took four and a half seasons. It was gradual and mindless for them (with some angry hiccups), to the point where, when they find themselves hanging out willingly, it freaks them out.

Blair: “Dan and Blair, individual entities, two proper nouns separated by a conjunction”
Dan: “Or a comma, if mentioned in a list.”
Blair: “Which is rare, since we have nothing in common and are, in fact, opposites.”
Dan: “The kind of opposites who do not attract.”
Blair: “Most definitely not.”

Their friendship is of the purest, simplest kind. They both enjoy cinema, art, and books. They watch movies together and comment on them. On occasion, they discuss their differing points of view on art and books. It turns out, they have a lot in common and always did. Dan’s judgment for her becomes teasing and Blair’s once cutting words become playful banter.

Given how vocal they have both been about their dislike for each other, they’re both shameful and loathe to admit they’re friends. They sneak around, which raises suspicions that they’re having an affair, which leads to:

“Blair, we kept us a secret because we were afraid there was something more.” / “Just one kiss; then we can know without a doubt.”


Badly Timed Unrequited Love

Dan and Blair have polar opposite reactions to their first kiss. Dan is “ass-backwards crushing on Blair Waldorf”, in Eric’s (Serena’s brother) words. Blair becomes convinced she is meant to be with Chuck. All this happens more than halfway through the fourth season, just before Louis comes to New York looking for Blair.

Blair and Dan start their tentative friendship before that. He becomes her rock from the time Chuck is courting another woman all the way through her marriage and subsequent divorce to Louis. The problem is, from the moment Dan kisses Blair, his feelings change.

For the most part, Dan is there for Blair, and helps her because he cares about her, but some of his actions start having ulterior motives. He wants her.

Blair is a hot, scalding mess through this time. Her feelings are all over the place, deciding to be with Chuck, then Louis then Chuck again, ad nauseum. The last thing she needs is a third romantic option. To his credit, Dan doesn’t dump his feelings on her, recognizing the spot she’s in and trying, genuinely, to be there for her as a friend. But this is Gossip Girl, and Dan’s feelings won’t remain secret forever.

He finds an outlet in a book he titles Inside, which his friend Vanessa sends to a publisher without his consent. When he gets a deal for it, ambition gets the better of him. It is through this book that Blair discovers Dan’s true feelings for her.

“Dan loves me for me.”

There is quite a bit of emotional manipulation on Dan’s part, albeit indirectly. The book suggests very heavily that Dan is the underappreciated best friend that the girl doesn’t notice. Peak “good guy” thoughts, even though he was writing them into something like a diary at the time.  Nevertheless, it is the catalyst for Blair to go to Dan.

A Blair Who is Content Is Not a Blair

“You’re too happy. Content. I’m worried you join cult.”


Back when Blair and Dan were secret friends, Blair’s closest confidante, Dorota, commented how Blair was “too happy”, so something must be wrong.

The start of Blair and Dan’s relationship wasn’t smooth sailing. There was an issue of Serena’s jealousy, first, even though they hadn’t been together in years. Then, they had an awkward first sexual encounter which rose doubts about their compatibility. Blair struggled with jealousy over Dan’s momentary success with his book. They both agonized over the clashing of their worlds.

“Our relationship isn’t about choosing one world or another. Our relationship is our world.” – Dan

Dan knows who Blair is. He does not idolize her. But he doesn’t excuse her behavior either. He sets his personal boundaries, without trying to control her. He brings out the best in her; when she’s with him—she’s hard-working and thoughtful, she is brilliant and fierce.

Yet the moment things calm down between them, Blair begins to get antsy. So does Dan. She starts reassuring herself everything is fine but goes to Chuck’s aid as soon as he asks. Dan’s fear that Blair will eventually leave him for Chuck, as she has done literally all men in her life, gets the best of him.

On Blair’s part, there are unresolved feelings and the enduring idea that love should be painful and dramatic (remember Chuck telling her she’d be “bored within five minutes” with a relationship like Dorota and her husband’s). Blair does not know how to navigate a non-abusive, relatively drama-free relationship. So as soon as things stabilize, she goes looking for that intensity and drama.

That was always going to happen. But perhaps if Dan hadn’t acted paranoid and irrational, the result would have been different. Instead, he stalks her… Then again, that was always going to happen, too. Dan is someone who prejudges everything and everyone. Blair didn’t need to cheat or betray him for him to get all “follow that car” on her.

Ultimately, Blair leaves Dan for Chuck.

Blair’s brief reencounter with Nate in season two and her relationship with Dan were the only relationships with a healthy amount and type of conflict. Blair and Dan had their differences, but it is established—in dialogue and in action—that Blair feels comfortable with Dan. She feels safe, and is “content”, as Dorota put it. So why would she leave him?

There is an argument to be made Blair didn’t really like Dan, but the knowledge of being loved in a certain way activated some of Blair’s insecurities. This guy loves you for you, why would you pass that up?

I think it goes a bit deeper than that. There was potential for Blair to develop feelings for Dan organically, perhaps there were even feelings buried deep that Blair wasn’t ready to face. Either way, the problem was timing.

At this point, Blair is still caught up an unresolved cycle of abuse with Chuck, and about to get out of a marriage to a man who ended up being emotionally abusive to her, too. She is not in a healthy mindset. Blair is not ready for Dan—or anyone else, for that matter.

Serena, the Trump Card

When Blair chooses Chuck over Dan at the end of season five, Serena didn’t seem to be the biggest factor at play. Blair had been spending a lot of time with Chuck, her diary had been revealed where she had written she still had feelings for Chuck, and Dan was expecting her to go to Italy with him for the Summer.

However, I am partial to the thought that, on a subconscious level, Serena played a huge part on Blair’s ultimate decision.

Serena and Dan had a very intense, ongoing relationship. Dan had her on a pedestal, and Serena quickly learned she could step all over him and he’d always come back. She could leave him, be with someone else, and the second she cried for help, Dan would be there. Serena wielded this power over him many times. This behavior on Dan’s part didn’t stop when he was with anyone else… until he was with Blair.

Eric: “This is the first time I’ve seen you pass up a chance to save Serena. And you’re alphabetizing. What’s up?”
Dan: “I kissed Blair Waldorf”

Serena did not take it well.


“Well I’m really glad you two found each other because you sure lost me.” – Serena

Even after she’d told Blair she was not going to stand in the way of their relationship, Serena slyly went to Chuck and prompted him to do the dirty work for her. Even after things calmed down, Blair and Dan seemed to exist in a bubble outside of nearly everyone around them, especially Serena (and Chuck, duh).

Now before I go on, I want to make somethning clear. I do not think Serena is a bad person; she is a complex character in herself, and the way she behaved stemmed from her upbringing and the way her own society treated and viewed her. Most of the comments I make for other characters in this articl are exclusively trying to understand Blair’s point of view. Blair loves Serena just as much as she resents her. She is just as prone to Serena’s charms, and I do believe, with all my heart, that Serena loves Blair back.

Dan was the guy Serena kept in her pocket. She had laid her claim on him and taken him for granted in the meantime. And Serena is, always was and probably always will be more powerful than Blair in their friendship. Serena can make Blair feel like crap and come off as the victim. She is the one who can get everyone on her side no matter what the circumstances—a power Blair does not have. She is the one Nate loved, forever and always. Dan would always come back to her, eventually.

Just as Dan clearly had a fear about Blair and Chuck, she would have been completely right to have the same fear about Dan and Serena. It was never externalized. But going by everything we know about both Blair and Serena, if the latter wanted the guy for herself in the end, she would get him. And Blair knows this.

The Tragedy

By definition, a tragic character is the one who makes a fatal error in judgement that ultimately leads to their own destruction.

Chuck and Blair started out toxic. Every time they came back together, it ended in pain. Chuck sold Blair, she sabotaged his relationships, he declared war on her. She toyed with him when trying to choose between him and Louis, he literally tried to buy her back by paying her dowry—yes, there was a dowry, she was apparently married to a prince from the 1800s.

The pattern with Blair and Chuck is demonstrated time and time again from season one all the way through season five. It is highly likely that they will end in pain, again. And she chooses him, again.

Blair: “Dan is my best friend, and when we’re together it’s great. I feel strong and safe.”
Eleanor: “And with Chuck?”
Blair: “I’m vulnerable. He’s devastated me, but he’s also made me happier than I’ve ever been. I just don’t know which kind of love is better.”

Blair basically… spells out her entire character regarding love here. She literally describes the two main stages of an abuse cycle when she speaks about Chuck; the highs are very high, and the lows, devastating. And when talking about Dan, she doesn’t use the words “boring” or “okay” or “settle”. She feels “strong”, and “safe”. She chooses Chuck. And, well. Damn.

It’s heartbreaking. She says it herself: she doesn’t know what kind of love is right. Because she doesn’t know herself. In the next line, she tells her mother that maybe she shouldn’t care, because “if I was truly powerful, I’d be content without any man at all.” But Blair doesn’t know how to be content with a man (Dan), much less without one. She never learned how.

Who is Blair Waldorf?

She’s the woman who struggled from the word “go” to get some success for herself, and ended up accepting to run her mother’s company. Blair is Serena’s best friend, who won’t trespass into her “property”. She is the woman Chuck Bass pertains to own, and she ultimately lets him.

I can’t help but see Blair’s story as tragic. She worked so hard to escape Eleanor and Serena’s shadow, and ultimately settled in it. She pushed and pulled to get out of a cycle of abuse. She even almost recognized for what it was. In the end, she fell right back into it.  In moments, she was so close… so close to breaking free from the people and the society she’s let define her all her life.

Blair is the woman who could have been.

Nevertheless, Blair is only twenty-one at the end of Gossip Girl. She has time, and I like to imagine that later down the road, Blair broke free of it all and was finally able to answer that one question, not for anyone else’s benefit, but for herself.

If you got all the way to the end, thank you so much! This is a juggernaut. If, like me, you have any thoughts on Blair or some other character whose fate has always gnawed at you, I’d love to read them.

Images courtesy of The CW

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