In conversation with my previous post: few things are grosser, or more illegal, than early season 1 Chuck Bass.
In the pilot, our very first glimpse into Chuck’s predatory behavior is when he empties his father’s hotel kitchen so he can lure drunk Serena in there with the promise of a cheese toastie. “If you’re looking for a way to thank me, I’ve got a couple ideas” he says calmly, before kissing and clawing at her while she shouts no.
Later on, in the same episode, Chuck coaxes Jenny to the rooftop at a party and forces himself on her as well, with Blair’s prior encouragement…
“Will C end up with a new victim?” the Gossip Girl voiceover chimes.
Luckily, Jenny was scared enough to text her brother beforehand, and Dan and Serena get there just in time. Chuck calls Serena a slut, and Dan gives him a black eye. It’s one of the only times I’ve ever admired Dan Humphrey.
“Chuck likes to brag about his conquests, not his victims”, Blair Waldorf assures Jenny the next day. Charming.

Even early on, Chuck is depicted to regularly have consensual sex, so his attempts at rape are most certainly an intentional flaunting of power. Unfortunately, instead of being a flawed character, in turn promoting awareness for sexual assault and noxious masculinity, he was just Gossip Girl’s resident villain, merely there as the token sleaze and a dramatic plot device. In the original books by Cecily von Ziegesar, the TV show’s source material, Chuck is a minor character who only cares about sex and money, epitomising Upper East Side evil – so it’s possible that the show’s writers didn’t intend for him to stick around very long. Perhaps it was an accident that Ed Westwick proved to be one of the strongest actors in the cast, quickly turning into an audience favourite. I will not even try to pretend that his array passionate fans didn’t include 12 year old me.
Upon obvious reflection, 2007 was NOT a woke time in human history. While people were probably disgusted with Chuck Bass’s actions, many fell in love with the character as he began to battle with ‘fixing himself’ and did their best to erase Chuck’s actions before his romance with Blair from their minds. Given the societal context of the middling early 2000s, and the fact this was a fictional character and not a real life human being, the audience’s denial was almost forgivable. To quote a Vox article:
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.
Constance Grady
As someone who likes writing scripts, and creating characters, and has been entranced by many flawed, anti-hero male characters in the past, like Don Draper, Walter White and Frank Gallagher, I can definitely see this from the perspective of the creators, who probably didn’t realise Chuck would become their main romantic lead, let alone a central character driving millions of views and birthing a questionable population of teen fangirls. Once you make a character a one-sided villain, it’s incredibly hard to backtrack on that later on and propel them into a sincerely believable redemption arc. The Gossip Girl writers probably felt they had done their best, but it was clumsy, and it remains alarming to this day how they tried to move on from these early plots.
There was plenty of trivialising dialogue about how Chuck used to be disgusting haha, but he’s a changed man now. I would have liked actual evidence that proved these claims.
And then in season 2, Chuck, who is depressed and alone at the time, apologises to Jenny. It’s a little half assed, focusing on his personal regret, and not the trauma he likely inflicted on her…
An even more astoundingly odd choice, was in season 4. Chuck had just effectively sold his girlfriend Blair to his seedy uncle in exchange for getting his Empire Hotel back. Blair decides she can move on from this, and plans to meet him at the Empire State Building, where he said he’d be waiting for her one last time. Dorota gives birth, making her late meeting him, and Chuck goes back to his suite alone, where Jenny Humphrey has come to look for Nate. The writers genuinely sat down at this point and were like, haha, now let’s make Jenny consensually lose her virginity to the dude who sexually assaulted her in season 1. Dan finds out and punches Chuck again, which arguably wasn’t called for in the realm of the story, since it was in fact consensual, irresponsibility of the scriptwriters aside.

At this point, we’re done being disappointed with his behaviour. We’re maxed out…but Chuck was intoxicated in season 4, got angry at Blair, and punched a hole through the window behind her, the glass cutting her cheek while he yelled ‘You’re mine!’. He was still treating Blair as an economic unit, and regularly trying to win her over with his wealth via clothes and jewellery. (Not out of character for these obscenely rich, shallow young adults, but still yuck).
I like to think we all understand how societal context can make older shows extremely problematic, and borderline unwatchable at times, as they age. And anyone who writes, understands the difficulty of executing a hefty character transformation, especially one that was unprecedented. Mostly all of us are guilty of rooting for a deeply flawed character who we would be a lil bit scared to be left alone with in real life. Overall though, I think the writers of this show could have come up with a little bit better of an excuse for his rapist and emotionally abusive tendencies than “I’m Chuck Bass”.
As Gossip Girl fans, and as scriptwriters, we should watch this show with a large grain of salt and learn from this.
