Who was the most toxic person on Gossip Girl? In the Upper East Side, the idea of toxicity is really relative, especially when there are million dollar trust funds and high-powered alliances at stake, but Gossip Girl did feature problematic relationship patterns, bullying, gaslighting, intimidation, and enabling behavior, which weren't recognized as toxic.
The show has received flak over the years for glossing over the glaringly toxic personal dynamics under the veil of ‘rich people, doing rich people stuff.’ But even the non Upper East Siders have proven to be quite dangerous in their own right.
Rufus - Least Problematic
Rufus was perhaps the only person on the show who never had a vendetta against anyone, not even his ex-wife, even though they had a bitter split. He was father to Dan and Jenny, and was very aware of their angst against the Upper East Siders, specifically because he had always steered them away from leading shallow, fame and money-obsessed lives, since he himself led a low-key life. Not only has Rufus always been there for his kids, he’s also a good friend and ally, and he was genuinely shocked to find out that his own son Dan was Gossip Girl and did so much damage to other people, often unprovoked.
Dorota
Sure, she had enabled Blair’s devious antics for years, but Dorota was also a steady voice of reason in the Waldorf household. It goes without saying that she was much more than a housekeeper, she was also the keeper of many secrets and was acutely aware of anything and everything that was going on.
But there was also a wholesomeness in her character design, which is why Blair didn’t always reveal her nefarious designs to Dorota, since she would obviously warn her against pursuing them. She was also someone who wasn’t afraid to be honest, and who didn’t judge, and had proved her worth as an ally many times.
Lily
Lily believed in tough love; even as a parent, she was always the first one to make the tough calls because she was very aware of how messy life in the Upper East Side can be. And though she gave her kids a lot of freedom, she knew how and when to rein them in. Like when she put Serena in rehab or warned her against getting engaged too soon or berated her abandoning a class to date her professor. It’s possible that Lily realized Serena was too much like her and she simply wanted her against making the same mistakes she did. However, she’s not wholly unproblematic, she has often made lives difficult for other people and can be quite cutthroat, but it’s impossible to dominate the Upper East Side without any fangs.
Jenny
Despite her personal hang-ups Jenny was never someone who directed her toxicity at another person just for payback. And though it’s eventually revealed that Jenny did help Dan with some of Gossip Girl’s work, it’s difficult to determine how involved she was since she didn’t stay in New York at all. But she herself had been relentlessly bullied by Blair, and even Blair's mum Eleanor.
Jenny’s exile from the Upper East Side helped her because she found some perspective and realized that the world is much bigger than the Upper East Siders. She was also very self-aware, even when she was a young designer and since she knew how bullying and oppression feels like, she would never do that to someone else.
Nate
This may sound controversial considering his history as an enabler but it’s important to acknowledge Nate’s transformation on Gossip Girl. Season 3 onwards, Nate starts realizing more clearly what he does and doesn't want, and that drives him towards some reprioritizing. Many times, he comes across as the voice of reason, warning his friends against giving in to their pettiness; he doesn’t just work on himself but also goes out of his way to help his friends stay out of trouble. He constantly looked out for Serena and could see she was on dangerous grounds even before she herself knew; and he constantly supported Chuck through his personal crises.
Serena
Serena, at her core, was never someone who’s driven by vengeance or bitterness. She has often been ousted from her friend circle and has been made to feel isolated, and yet she never schemed to get payback. She was aware of her privileges and also about how she was perceived, and many times she chose to step away, although she wasn’t always the best judge of character.
It's fair to say, Serena has been the victim of her social culture more than once. And though Serena has done some terrible things (she even made a sex tape with Dan just to get back at Blair), her priorities, unlike Blair weren’t all about hurting others. It was only when she felt acutely threatened did Serena think of doing something potentially hurtful.
Dan
The Gossip Girl fandom is still reeling from the revelation that Dan was Gossip Girl all along; and though he led the tirade against the mean, insidious Upper East Siders, he himself did a lot of damage to people’s lives as Gossip Girl, and many times his attacks were simply unprovoked. Not to mention he gaslighted both Serena and Vanessa and was pretty okay with lying. But Dan’s biggest sin is perhaps his sense of delusion, he never once admits to himself that Gossip Girl wasn’t his way of blitzkrieging a social circle but actually a means of gaining entry into the circle. He simply despised the fact that he was never seen as an ‘equal’ by Serena and her friends. So, in hindsight, Gossip Girl was just a teenage revenge blog that became too big because Dan simply refused to work on himself.
Blair
Pop culture has perhaps never experienced a teen so vengeful and intimidating as Blair Waldorf, who thrived on other people's traumas. The Queen B title was so important to her because she realized that she had very few allies, and people usually flocked to her because of her social cred. So, she always needed to be surrounded by a clique of yes-men who would agree with whatever she says. She oppressed vulnerable people, and it's important to note that most of her victims would be teenagers without any of the privileges Blair has access to. It’s important to note that Blair herself has been a victim of her own social culture many times, but instead of reflecting on herself and her privileges, each setback only made Blair all the more dangerous and scathing.
Chuck Bass
Chuck Bass has become the poster boy for the toxic boyfriend and quite rightfully so; Chuck was a terrible partner, and an even worse friend. In season 1 he was established as a predator, which is why Gen-Z audiences watching the show were quick to denounce Chuck’s problematic patterns. He tried to force himself on women, he literally traded his girlfriend for a hotel, he could not let Blair be happy if she wasn’t with him, and was simply too preoccupied with his own life to notice others’ problems. So, while his friends were able to work on their hang-ups to a certain degree, Chuck remained pretty much the same.
Georgina
What did Georgina really want? Much like the Joker, she simply wanted to see the world turn upside down, however unlike the Joker, her bitterness seemed to be quite rudderless. It was clear that she despised Serena and Blair and reveled in their downfall, and actively plotted against them throughout the show. She was also opportunistic and planned on passing off Milo as her and Dan’s son, although she knew he was not the real father. Season 5 onwards, she grows even more heinous because she becomes Dan’s agent and actively pushes him to spew venom in his book, specifically against Serena and Blair. But in spite of her bitterness and angst, it was never really clear as to what she really wanted for herself.