The Chuck Bass Paradox

You know you love him. XOXO

(This post contains spoilers.)

The first thing you notice about Chuck Bass is his wardrobe: ascots, bow ties, sweater vests, sailor jackets, flowy trousers, scarves, scarves, scarves. This guy better have money otherwise he’d never get laid dressing like this. He’s like a parody of the Richie Rich cartoon.

The other thing we learn right away is that he’s kind of a dick.

Right out the gate when we enter the world of Gossip Girl, he sexually assaults 14-year-old Jenny Humphrey at the Kiss on the Lips dance, and nearly does the same to Serena.

We’re meant to laugh this off the way we overlook the fact that 16- and 17-year-olds are having multiple martinis at lunch. He’s Chuck Bass. Date rape of underage girls and sex trafficking are his “thing.”

. . . ascots, bow ties, sweater vests, sailor jackets, flowy trousers, scarves, scarves, scarves.

He’s Mephistopheles. He says things like: “I do my cardio in the evening.”

For a minute, I didn’t understand the sexual innuendo, but instead pictured him in a velour tracksuit and an ascot on the elliptical—which wouldn’t be that far off considering his other workout clothes.

As Chuck says in Season 1, “The Wild Brunch,” “Don't mock the scarf, Nathaniel. It's my signature.” 

Throughout Season 1 we’re pretty sure that Charles is always going to be a villain. He is a definite bad guy, but that all changes over the course of the show. Why do we give bad guys endless second chances? What could account for our undying tenderness toward abusive pricks?

We want so much for them to “grow out of it” and find the right woman to tame their inner beast.

If this story were told from the perspective of the girls Chuck trafficked, we might not be so forgiving. Or if we were Jenny Humphrey or the many other people who weren’t lucky enough to be rescued in time, we would not see his rapey-ness as just a minor character flaw.

When he does apologize to Jenny in Season 2, she doesn’t say, “Oh, that’s OK.” The look on her face is cold and disgusted, tears welling up in her eyes—indicating that Little J would never forget the trauma of the moment when she thought she wouldn’t be able to get away.

In the end, she sleeps with him willingly and even loses her virginity to him. Even though she consents to this specific encounter, the earlier attempted rape looms large in the subtext.

She is wrecked. She looks like an abuse survivor afterward because she is one—it’s just that the assault started years before and finished with her sacrificing herself to the beast.

Little J would never forget the trauma of the moment when she thought she wouldn’t be able to get away.

The real Chuck Basses of the world are not likely to change on their own, especially when everyone turns a blind eye.

So what’s the paradox? As much as we hate the devil, it wouldn’t be the same world without him. As much as we hate Chuck Bass, he comes with the package. Our only hope is to redeem him. We can’t erase him or forget about him, but he has to reform. He can’t just keep raping and pillaging.

It's more likely that without outside help, Chuck Bass will relapse. It might be years later, but at some point, his demons will catch up to him and he’ll default into his comfort behaviors (e.g., mercilessly exerting his power over others at his own whim).

Maybe he’s able to maintain a perfect façade at home. Maybe he is the society husband Blair always dreamed of: Perfect in every way. Except he pays for sex with underage girls and he gets a little rapey at work. It seems easier to gloss things over and put a spin on it, pay out the victims, avoid the courts, keep the secrets.

As much as we hate the devil, it wouldn’t be the same world without him.

Or he’ll be driven mad like in Season 4, Episode 20, “The Princesses and the Frog” when Chuck punches through a window near Blair’s head—a shard of glass cutting her cheek. Gossip Girl narrates as Blair runs away: “Once upon a time in the land of Upper East, a beautiful girl fled from the beast.”

When Chuck is sued for sexual harassment in Season 3 and loses his hotel over it, we’re told that he’s being framed this time (“Some of those girls weren’t even in the country!) but it doesn’t change the fact that he is guilty of similar crimes a thousand times over and just hasn’t been caught.

By that point, we’re more likely to side with Chuck because we’re invested in his salvation. We’re more prone to side with him because we want so desperately for him to just be a good guy already. But does treating one woman “like a queen” make up for the harm he’s done to countless others before?

If all it took was one good woman to completely heal men who prey on girls and women, then we’d be living in a reformed society. I’m sure every survivor wants to believe that their abuser will change with enough love, but this doesn’t play out in the averages. Abusers continue to abuse unless there is something to break the cycle, not just once, but every time. And unchecked power will inevitably escalate to abuse of some kind.

Of course, we have the benefit of hindsight when watching Gossip Girl years later. What seemed like harmless fun in 2009 takes on a different tone in 2024.

The Upper East Side teens are exactly the kind of people who would’ve aspired to attend P. Diddy’s “white party.” In the problematic Season 5 of Gossip Girl, they gush on and on about what a great producer Harvey Weinstein is.

There are references to David O’Russell and Charlie Rose, both of whom have had their own scandals. It makes you wonder if all these men had the same publicist? Were they trying to get ahead of the bad press by wooing the GG generation?

In a weird “life imitates art” moment, Serena’s boyfriend Gabriel is played by Armie Hammer, who is pretty much a real-life Chuck Bass.

Coming from an uber-wealthy family himself, he understands this life of unimpeded privilege better than anyone.

I had a hard time watching these episodes given the accusations of rape and sexual assault against him. It’s not a leap of imagination to think that Chuck might have let his freak flag fly and tried to eat some people too.

The actor who plays Chuck, Ed Westwick, himself was accused of sexual assault (also not charged due to statutes of limitations and lack of prosecutable evidence), which begs the question: Where does reality stop and the fantasy begin?

It’s clear that Chuck and his family (aka, the Bassholes) aren’t the only ones perpetuating a hypersexual culture on the Upper East Side.

Chuck might have let his freak flag fly and tried to eat some people too.

The entire show is steeped in objectification of underage girls and boys. Cleavage is on full display even at the most demure occasions. Skirts could not get any shorter. Heels could not get any higher. Makeup could not get any thicker. Hair could not get any more blown out.

The creators of Gossip Girl didn’t have to dress the actresses this way. This was a choice to dress them in low-cut cleavage shirts with super tan skin and blown-out hair extensions and underwear shorts.

So, are we meant to judge the Upper East Siders for being shallow and sex-obsessed or does the fact that we’re watching this mean that we are?

We’re led to believe that it’s the kids sexualizing themselves because of their natural debaucherous tendencies triggered by privilege and bad parenting. But in the classic double standard, we’re urged to view the “good boys” sleeping with teachers and married women as sexy rather than abusive. Far from being portrayed as victims, Dan would probably call Miss. Carr the “best teacher ever.”

And was Nate always going to be attracted to older women or was he oversexualized by randy ladies who should have known better?

To bring down Chuck Bass and really hold him accountable would be to destroy this whole system, which is the only thing we know. A lot of us probably believe it’s “just the way it is” and it’s “natural” for powerful men to have free rein to sexually assault anyone. It’s a perk of the position. Maybe we want to preserve this immoral world because we fantasize about one day ruling it.

But by then, we’ll be tying our own ascots and rationalizing our own vices.

We don’t want to end the game when we still dream of winning. Who hasn’t had fantasies of success? Who hasn’t ever daydreamed about feeling powerful? We don’t want to tear down the empire when there’s still a chance we could sit on the throne.

We tell ourselves we wouldn’t be rapists and murderers and schemers and adulterers and child abusers. Not us. We just need to get those “bad guys” out of there and take the power into our own hands.

But by then, we’ll be tying our own ascots and rationalizing our own vices. “I’m Chuck Bass,” we’ll say. And that’s the only justification anyone will ever need.