A definitive ranking of every shitty boyfriend Serena ran through on Gossip Girl
Including all the ones you forgot about
I am not slut-shaming Serena van der Woodsen. If a gal wants to ditch her panties at 1OAK, sex up married politicians in the back of a cab, or have a pregnancy scare with more baby daddy possibilities than she can count on one hand, that's fine! I'm pretty sure that's what Ruth Bader Ginsburg fought for, according to the trailer of her surely-straight-to-DVD biopic I accidentally watched on Twitter!
But what I will do is love-shame Serena van der Woodsen. As I started power-ranking every rich dude she let hit it throughout the Greatest Show of Our Time, I noticed a pattern: she really thought she loved all of these guys! And that's the truly batshit insane thing about SVDW. So while I won't call her, say, the Bicycle of the Upper East Side, I can call her an emotional slut. And by the end of this list, I think you will too.
11. Gabriel Edwards
Before Armie Hammer starred in forgettable movies as Main Tall White Man, he starred in a forgettable Gossip Girl arc as Third Most Important Tall White Man (after Chuck and Dan but before Nate). Over the course of I think two episodes, Serena emotionally sluts it up so hard it makes a Bachelor contestant look like she's in it for the right reasons. Armie plays Gabriel Edwards, a southern businessman who she first met while he was dating her good friend, Poppy Lifton. So despite him being the serious boyfriend of one of her best friends, Serena gets so swept up in his Tall White Manliness that she "marries" him on vacation. He then proceeds to scam millions from her mom, her ex's dad, and virtually everyone who lives in her building.
HIGH POINT: Serena, like me, has a thing for guys with faces that look like cereal boxes. Who among us hasn't been hypnotized by beautiful, generic symmetry? I'll give her this one.
LOW POINT: The theft is up there, but I'm mostly offended that the writers kept making characters repeat that Gabriel is southern but offer absolutely zero evidence to support it. He didn't even attempt an accent.
10. Nate Archibald
Though I've basically got Us Weekly for brains, I'm having a very hard time recalling a single Nate plotpoint that didn't involve him fucking an older woman for money. I know Blair and Serena were both trapped in revolving-door relationships with him but…what happened in them? What did Nate do at all???? There was him sleeping with Duchess Catherine for money (who's Betty's mom on Riverdale, can you believe?!), then there was him sleeping with Diana Payne for money. Then he became the mayor, I guess. Everything in between is a blur, especially anything involving Serena — any time their boring blondness synched up, I would fast-forward through their scenes. It's because of this aggressive non-descriptiveness that Nate ranks towards the bottom. I would have put him dead last, but my boyfriend told me he once met Chace Crawford at a wedding in Texas and he was lovely.
HIGH POINT: When Dan made him gay in his book, which I would very much like to read! Why didn't they release it as a series tie-in?
LOW POINT: When he had highlights :-(
9. Ben Donovan
Sure, he tried to kill Serena because her mother got him falsely convicted of raping her! Sure, he always sounds like he's growling and sure, he's got the blank, liquid gaze of someone on a mood stabilizer. But that didn't stop Serena from diving into her most ill-advised relationship with her former boarding school teacher, freshly out of jail for her statutory rape. Maybe Ben wasn't directly involved in Vanessa, Jenny and Juliette's plan to drug Serena and leave her for dead beneath and overpass, but he did put all the pieces into place. And for that, I say thank you because it was by far the best of the absolutely bonkers late-season storylines.
HIGH POINT: When Ben lies and says he's tutoring to hide that he's actually a cater-waiter because he's embarrassed! It's so sad and sweet and cute and Ben is played by kind of an amazing actor.
LOW POINT: The completely unbelievable setup in which underage Serena and Teacher Ben travel across state lines to visit a library. Serena doesn't know how to read, duh.
So he and Serena never actually dated for real, but he was her date to the Kiss on the Lips party while Dan was too busy being literate with Vanessa in his garage-room. RichGuyIV, whose real name is the horrifyingly Anglo Edward Abbott IV, took Serena to the party and they had a very lovely 15 seconds of screen time during which he was dressed as…William Cornwallis, I guess? And he twirled her around a bunch. Which is really all a girl could ever want on the dancefloor.
HIGH POINT: If you pause the screen on his MySpace profile, his header quote says (*extremely Andre 300 voice*) "Lend me some sugar, I am your neighbor!"
LOW POINT: The MySpace also says the person he mosts wants to meet is Lindsay Lohan. Even in 2007, I thought that ship had sailed.
7. Tripp Vanderbilt
The first man to leave Serena for dead in a hospital bed! What a novel thrill that was. And while Serena's tryst with married politician/her ex's cousin wasn't unique in that it almost ended with her perfect skin grafted to Connecticut asphalt (Ben's murder storyline was superior), it was one of the very few times Serena's mom was right about anything. Remember when she had the fucking nerve to show up at Thanksgiving with him wearing that skin-tight lace catsuit and have a stare-down with his wife and Lily was like "Serena, you're not welcome in my home while you date a married man of an indecipherable age!" Yeah, file that under one of her few solid parenting choices.
HIGH POINT: When that first MMMM WHATCHA SAY cut the Thanksgiving tension like the serrated electric knife my dad uses to cut our turkey every year. I had the pleasure of watching Gossip Girl in real time as it aired, and I remember 15-year-old me SCREAMING over that scene!
LOW POINT: When you realize Tripp and Nate are bang-bros.
6. Aaron Rose
There are so many things I can't relate to about Gossip Girl: being that rich, being that beautiful, managing to bend time and space so I can get lunch at my loft in Williamsburg and be back to school on the UES within an hour. But we all relate to the Aaron Fucking Rose storyline. Who among us hasn't unwittingly entered a love trapezoid with a dirty RISD dropout and his bevy of Instagram-ready beauties, only for him to drop us lines like "I'm not going to explain who that girl was, I thought you were more mature than needing a label for this"? Who! Among! Us! While Aaron never did anything especially insidious, he's just such a prototypical shitbag that I'm angry he ever dared darken Serena's condo's doorstep. Or elevator step, as is the case with the Bass-Van der Woodsen compound.
HIGH POINT: I guess there's something to be said for his long-term memory capacity.
LOW POINT: Every fucking sweater he had to nerve to wear.
5. Steven Spence
I have to be honest with you, dear reader(s). I remember…next to nothing about Steven Spence and his arc. I remember his Serena-aged daughter was yet another one of Nate's inappropriate love interests, and I remember Serena lied to him and said she was from Wisconsin. A quick Wikipedia sesh reveals that Steven and Lily hooked up in their youth! And the worst part? That wasn't even enough to keep Serena away.
HIGH POINT: When Steven finally says what everyone's thinking: Serena is ridiculously immature.
LOW POINT: Steven pulling strings so Serena can head the Central Park Conservancy Gala. I used to be an editor at a society magazine so to this far-fetched subplot, I'm uniquely qualified to say looool no.
4. LAX Bro James
Again, not a proper boyfriend but he was part of such a glorious episode that it would be a crime to leave him out. You know the episode, it was series defining — Dan goes on a date with Amanda (played by Vanderpump Rules loser Laura Leigh!!!!!!!!!), and Serena gets back at them by crashing with this Abercrombie'd lunk and letting Penelope throw a Nairtini at her acrylic-ass wig. To which I say: wig!
HIGH POINT: His tiny gold chain, straining against the ginormous circumference of his neck.
LOW POINT: He thinks STK is the spot to hang at.
3. Colin Forrester
He's a billionaire. And a businessman. And a best-selling author. And a guest lecturer at Columbia. And under 30 (barely). And was a womanizer until he met Serena who made him reevaluate his life choices. And…Serena let him slip through her polished fingers! While it's true he was Teacher Ben/Murderous Juliette's cousin, that wasn't even what split him and Serena up! They just randomly decided to part ways which is so incredibly dissatisfying, I know for a fact some straight male writer is behind it.
HIGH POINT: When he was willing to resign from Columbia to be with Serena, who het met just days earlier.
LOW POINT: None! And forum commentators agree with me:
2. Dan Humphrey
Though many have said Dan was the biggest fuckboy of the series, I can't help but feel a little sorry for LonelyBoy. Yeah he was a total asshole, but he was growing up while trying to navigate the treacherous new social waters he found himself suddenly treading by managing to snag a date with Serena. And specifically within the context of his relationship with Serena, every bad thing he did is cancelled out by all of the equally bad things she did to him. Even though I'll always believe Blair and Dan were a better match than Serena and Dan (hate about it, I don't care), I can admit their opposite-ness evened out. Serena was…free-wheeling while Dan was more rigid and lame. Both took themselves waaaay too seriously, and both were consumed with what the other person represented — you know, like those "we're from different worlds!" talks they were always having despite going to the same high school? In the end, it was weird that they got married and it seemed like a huge cop-out, undoubtedly by the same evil writer who orchestrated the Colin Forrester breakup. But look at it like this: the person Serena loves most in this world is herself, so who better to end up with than the guy who spent a decade of his life obsessively chronicling her every move for an anonymous website? A match made in heaven.
HIGH POINT: Every arc in which he had to prove that just because he was upper middle class instead of upper class, he was worthy of Serena's time and affections.
LOW POINT: Any time he wore a vest.
1. Carter Baizen
Stay with me here: Carter is the guy Serena should have wound up with. Like Serena, Carter was always harping on and on about how he's "changed" and "not the same person I was!" while railing against his wealth and privilege. He did humanitarian work around the world and even helped Serena track down her dad, the lesser Baldwin. Of course he's got his demons like a crippling gambling addiction and sky-high debts to violent foreign dignitaries, but you could tell he was a good guy at heart. Eventually, he was written off the show so Sebastian Stan could finally start making at Marvel money and Serena could do back to playing Musical Dick with Nate and Dan. But mark my works: Scarter (that's Serena and Carter, keep up) could have been legendary.
HIGH POINT: When he risked getting the shit beat out of him by Bree's redneck cousins to see Serena.
LOW POINT: Every time his credit card gets declined. I've been there too but get it together, dude.
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