Sometimes Gossip Girl is Gossip Boy: A Retrospective on Dan, Blair and Serena
Can you keep a secret? This is sort of my own personal Gossip Girl - XOXO
In light of the very recent passing of Michelle Trachtenberg (the greatest to ever do it), I want to talk about one of my favourite television programmes of all time and the reason why I have a campy little semi-secret blog, Gossip Girl.
I came late to the party with Gossip Girl after my best friend (the one from Horse Girl) raved about it for years. I started watching it on Netflix long after it had finished during my teenage years but at that time I was feuding with the friend in question and I found it too upsetting and stopped watching because I saw me and her in Blair and Serena. Make no mistake, I know people often compare themselves and their friends to the characters but, we were Blair and Serena.
As an adult, I decided to try again and became absolutely obsessed because of the sense of nostalgia it brought and how much I related to the characters, fortunately or unfortunately. I was a French obsessed brunette with a thing for film and fashion, sure, but I also saw myself as a bit of a Dan, for better or worse. An outsider, often late to the party, often caught up in too many things, in too deep to realise it. Ironically, I also have a secret blog that isn’t very secret and I used my first ever professionally published piece to slander the Serena to my Blair. The kicker was, I called her Sabrina the entire time in true Humphrey fashion.
Gossip Girl is not aspirational, but it is. It’s supposed to show the viewers what big time New York wealth looks like and fabulous outfits and parties every episode. But equally, it shows how irrevocably messed up this world makes people. We see it through Dan and Jenny, the outsiders from Brooklyn (back when Alex McCord was uttering “I am in Brooklyn trying to survive in this economy!”), how they slowly become corrupted by the world they try so hard to be part of. Jenny bears the brunt of this especially, since she’s a girl and a direct threat to Blair in every single way. After all, the nail in her coffin comes when she and Chuck sleep together in incredibly icky yet technically consensual circumstances. Jenny cannot be part of that world because it’s alright for everyone else to have romantic moments with each other, but whenever she goes after one of the boys or one of the boys goes after her, she needs to be exiled away to Hudson.
I had to actually look up Hudson during the rewatch because I do not know anything about New York State and it’s actually really cute. I kind of want to visit it.
Anyway, I think the way that Gossip Girl treats its women is fascinating, even with the 2007-2012 time period to consider. We have Little J, the aforementioned Jenny Humphrey, who tries her best to become one of Blair’s underlings only to be given the title of Queen of the School once Blair graduates. Then she turns goth, gets into a bad crowd (mostly meaning my favourite of the random mini characters, Damien Dalgaard, ambassador’s son and Upper East Side drug dealer), becomes a teen fashion designer, pursues Nate and sleeps with Chuck and then is exiled like Napoleon for War Crimes against Blair. But really this entry of the Gossip Girlypop blog, Readers Wanna Know has got to be about Blair and Serena.
It really is Blair’s show and it becomes more obvious as the seasons go on. It’s basically the Blair and Chuck toxic Bonnie and Clyde love story but then it’s also randomly The Age of Innocence about Blair and Dan. Sometimes Serena is involved in this because she’s supposed to be the endgame character for Dan but really, if you’ve read The Age of Innocence, you’ll notice that Serena is basically serving as May Welland. They even have a very iconic early episode where the school play is The Age of Innocence and she plays May (I think, I need to rewatch it, I fear). Blair is who Dan really wants, but he can’t seem to land her because she’s always going to be in love with Chuck above anyone else.
Blair is complex and my favourite character. She’s so terrible at times yet there’s so much within her character to root for. She’s a slut shamer just as all the boys are, she’s certainly not what anyone would ever call “a girl’s girl” and yet, she inspires a sense of wanting her to succeed regardless of her failures. She’s a girl who was abandoned emotionally by her busy mother and then physically abandoned by her father when he moved to Paris to be with his boyfriend and torpedo his marriage and family life in New York.
She has an eating disorder, a controlling streak, a need to win at all costs and prove herself. Her best friend is a beautiful and mysterious carefree blonde while Blair needs to follow her own rules so rigidly that she drives herself crazy in the process and can’t understand why no one likes her as much as Serena. She’s in an abusive relationship with Chuck, she’s in a toxic relationship with Prince Louis and she’s in a sham relationship with Nate. The only person who has ever seen her for herself in actuality, is Dan.
Is this becoming an “in defence of Dair” blog post? I’m not sure, but I do love them together because they do, for better or worse match each other’s freak. Dan is no prize pig at the fair either, he’s largely insufferable, secretive and generally so “woke-feminist-hipster-writer-idiot” that I do find it harder to root for him than Blair. But in the areas of Blair’s life where it matters like her real interests and her passions, Dan shares them.
Blair is a film buff and often references films in conversation or in her little dream sequences. Chuck seems to generally understand what she’s going on about most of the time, but they never really have bigger conversations that we see about specific films or anything like that. But with Dan, we see this a lot. We get the trope of enemies to reluctant friends to lovers and we even get a scene referencing the ultimate film in that genre to me, When Harry Met Sally, in the scene where they both call each other while watching the same film at the same time just so they can discuss it as though they were both there physically with each other. That’s probably one of the most romantic moments in the whole series because it’s something so shamelessly intimate without the intimacy of physical acts.
Blair and Dan talk literature and film and go see Nanette in secret while everyone thinks they both have secret dates which eventually blooms into Dan realising he actually does have feelings for Blair. Unfortunately for him, she’s not into it and promptly moves into her getting engaged to a Monegasque prince arc plus her actual physical affair with Chuck arc. Dan is left reeling but also he’s an insufferable writer and like all annoying writers (this is me talking about myself here), he puts pen to paper and writes a slam dunk of a hit piece against literally all his friends.
Yes, his book is published under false pretences since Vanessa finds and steals the manuscript and magically gets him an agent and publisher through the strength of the book itself, but Dan wrote it and revelled in his notoriety as a literary celeb when it was released into the world. But the only one who did not, surprisingly, get a nasty narrative spun about them through a ridiculous (yet very amusing) roman à clef was Blair. She, as Claire, was basically written as the perfect woman, the one who Dan’s self-insert is in love with and the one who he actually and so very obviously wants.
Meanwhile, Serena, by contrast, is rarely shown to really have much of a deep conversation about anything. She and Dan joke around and tease each other in a way that feels like they really get each other, but as the series goes on, Serena becomes even more avoidant somehow and rarely stays in the room long enough to have a conversation with anyone. We never even really get a proper resolution to Dan and Serena before the last scene which is a five year time skip and their wedding. I wonder how many times they broke up and got back together in that time.
She’s always billed as the great big mystery girl. Ellen Olenska (to continue this Age of Innocence thing I have going on) in terms of how she arrives back to New York in a cloud of intrigue after skirting off away, telling no one and abandoning everyone. In the beginning, she actually gets the more sympathetic edit since we see how Blair wants to destroy her and how Blair would be a terrible enemy to have too. But as the show goes on, Serena is just as bad as the rest of them, maybe even worse than some.
She has terrible things happen to her, like the Pete Fairman thing where he died in front of her of an overdose. Her mother is a terrible parent and is too interested in her next boyfriend or husband to notice her daughter is a drug addict and her son is suicidal. Her father abandoned her too and she had to basically raise her brother, Eric. She gets herself involved with the more dangerous fringe characters like Carter Baizen (who I love) and Georgina Sparks (played by the great Michelle Trachtenberg, my Ice Princess Forever) in a way that’s supposed to spell her doom, but she always finesses her way out. Serena and Jenny are actually very alike and it seems almost that Jenny was trying to be Blair in the beginning then switched to wanting to be Serena, which is insane for the optics. Crucially, we all need to remember that Lily and Rufus, Serena’s mother and Dan’s father, respectively, were once lovers and had a secret baby together and we’re all just supposed to accept that and move on. Jenny is trying to emulate her step-sister-slash-one-time-girlfriend-and-eventual-wife-of-her-brother, okay? Normal, fine, cool.
Right up until the end, Serena gets a nastier edit from Gossip Girl than Blair because Serena is the one who actively messes Dan around the most. She leaked a sex tape between them in a way that would now be viewed as some form of consent issue/ assault since he was not aware he was being filmed and then it was broadcast out to the world. But this was in the era of Paris Hilton and Kim Kardashian and it wasn’t considered as big of a deal, especially if a girl did it to a guy. She constantly leaves Dan in the lurch regardless, and she really only did all of that just to make Blair upset since Blair and Dan were getting too close anyway.
Never mind the fact that Serena slept with Blair’s longtime boyfriend Nate which was the inciting incident of the entire show. In fact, Serena sets the sex tape scene up exactly like how she had slept with Nate, same location and vibe and everything. We were watching the pilot play out again before our eyes and it was all made explicitly to hurt Blair. Serena is the villain here and she sort of becomes worse than Blair in trying to defeat her, which we have already seen happen (in a way) to Jenny.
But the reason we see these women like this, always pit against each other and always fighting over boys, is because we actually see them all through the catty eyes of Gossip Girl herself. If you haven’t seen the show and don’t want a spoiler look away but it ended in 2012 so I think I’m okay to tell you that the titular Girl herself is none other than Dan Humphrey. There is some serious misogyny in how we see all the women on the show, even when they get good edits like Blair. She’s still a bitch, still needy and still absolutely has to have a man, even if it’s Dan’s biggest opp, Chuck Bass.
Dan’s whole schtick, like Newland Archer (Age of Innocence) is that he’s so woke about everything and everyone, especially women. He’s different and an outsider so he considers himself more real than everyone else in his school and later social group. He’s confronted with this during the publication of the book arc but fails to actualise it, since he literally is Gossip Girl. He’s self-important and just as self-involved as the rest of them, though that isn’t exactly new information. But I think that perhaps the characters in Gossip Girl itself start to almost become creations of Dan Humphrey.
I think we see the worst of everyone as the seasons go on because Dan hates everyone, most of all himself. The only time we see the good is when Dan sees the good. We see happy and sunny Serena in the beginning because Dan is intrigued with her and in love with her (maybe). We see smart and serious Blair towards the end because Dna is definitely in love with her for her mind as as as her beauty. We see annoying Jenny because she’s his annoying little sister and later we see slut Jenny because allegedly she wanted that edit herself– however, I think some of Dan’s own thoughts filtered in too.
We see inoffensive Vanessa, Dan’s childhood bestie who has unfortunately fallen in love with him in the beginning, only when Vanessa isn’t a threat. When she messes with Dan (or Serena at this point), she’s suddenly the most annoying character. We see scheming and wild Georgina filtered through the stories Serena tells us in the beginning, but then we see nothing but bad things from her because of course she has also messed Dan around too.
Overall, I think this is what makes Gossip Girl so compelling and it will stay that way for years to come over its flop of a reboot. It was a smart show that had flaws and did get worse as it went on, possibly a little too long. It referenced itself and the world around it at the time but it was never afraid of a highbrow and random literary or cinema reference. After all, one of American literature’s most beloved works, The Great Gatsby, is completely filtered through the perspective of the most famous unreliable narrator possibly ever. Dan is a Nick Carraway trapped in the shadow of wanting to be Gatsby and in a way, aren’t we all?