The Gossip Girl finale has a lot to answer for. It was pretty much a fiasco from beginning to end, but probably the worst sin of all was how it turned Dan and Serena’s once pretty adorable on-off romance into the creepiest thing ever. The revelation that Gossip Girl was actually Dan all along probably seemed like a great ‘OMG!’ moment in the writers’ heads, but once your brain starts doing backwards calculations you’re like ‘Wait, what about all those times we saw Dan text Gossip Girl? What about that time Gossip Girl slut-shamed Dan’s sister? IS DAN LITERALLY INSANE?’
Dan had been increasingly terrible for about three seasons before this point, treating Serena like crap despite her supposedly being the girl of his dreams. But after it turns out Dan’s also been anonymously stalking and humiliating Serena for years under the guise of GG, she doesn’t run a mile and file a restraining order. Oh no. She marries him. Because nothing says ‘I love you’ like an anonymous poison pen blog! In conclusion, Dan and Serena are the worst.
9. Nate & Vanessa
We could write a whole essay about why Nate and Vanessa made no sense as a couple, but who would even care enough to read it? Nobody was really shipping Nanessa (?) – their romance was like a bad penny that just kept on coming back through the first three seasons, even though their scenes together were always pretty flat. They always felt like a backup couple, thrown into the mix to create conflict in relationships we actually liked, and it was a relief when they finally called it quits after backpacking through Europe.
8. Rufus & Lily
Is anyone else still kind of bitter that Rufus and Lily didn’t end up together? They were basically an adult version of Dan and Serena (minus the creepy finale), but there was a real spark between them, even though Lily’s preference for douchey millionaires was always going to make it impossible for her to choose Rufus in the end. By the time the pair’s long-lost secret love child returned from the dead in season three, it really felt like the writers had no idea what to do with them any more. So Lily ended up with William Baldwin, and Rufus ended up with singer-songwriter Lisa Loeb, and nobody lived happily ever after.
7. Nate & Blair
Given the way we were introduced to this couple – with Nate having just cheated on Blair with Serena – it was always going to be tough for them to recover, especially because neither of them really seemed all that into the other. When you get together in junior high, chances are you’re going to grow out of each other before you graduate high school.
Even when Nair (Blate?) briefly got back together late in season two, it just felt like a doomed attempt to cling onto the past, especially because they were both in love with each other’s best friends. Their friendship remained cute and consistent long after their romance ended, though, which earns them a respectable seventh spot.
6. Serena & Carter
Okay, admittedly our view of Carter Baizen might be skewed by Sebastian Stan’s role in the Captain America movies, because it’s hard not to ship anybody with Bucky Barnes. Serena and Carter were never going to be a long-term thing, what with him being kind of a shady drifter and her having at least vague aspirations to do something with her life, but they were hella fun together and Stan had more chemistry with Blake Lively than almost any of Serena’s other beaus. Had the finale ended with Carter rocking up to whisk Serena away from her ill-advised wedding, The Graduate style, we would have been more than okay with that.
5. Dan & Vanessa
From the moment Vanessa showed up in Brooklyn wearing her unresolved feelings for long-time BFF Dan on her sleeve, it was clear they were going to hook up eventually. What was surprising was just how well they worked together as a couple, once that threesome with Hilary Duff forced them both to acknowledge the obvious.
Basically every single good thing that ever happened in Dan’s career was because of Vanessa, and she was the only person who could relate to him creatively – even though she was by all accounts a way better writer. Dan was so terrible by the show’s end that it was hard to ship him with anyone other than loneliness, but had Vanessa still been around she might have smacked some sense into him. Or at least inspired him to do something better with his time than be Gossip Girl.
4. Dan & Blair
We could have had it all, guys. Remember the very first time Dan and Blair shared a scene, in season one’s ‘Bad News Blair’ (above), and it was unexpected and lovely and a totally authentic moment of connection between two characters you’d never expect to connect? Their sparky frenemies dynamic remained one of the best things about the show for a long time, and as the Chuck/Blair relationship became increasingly toxic in seasons three and four, it began to look like Dair might end up being the true love story of Gossip Girl.
But then… Something weird happened. We’ll never know exactly what went down in the writers room midway through season five, but Dan transformed from a sweet guy into a sociopath, sabotaging Blair’s wedding and isolating her from everyone who wasn’t him. Eventually the whole relationship was later retconned into an afterthought, with Dan claiming he’d only ever wanted Blair because he was afraid of his love for Serena. Or something. We’d given up caring by this point, and seemingly so had the writers. RIP, Dair.
3. Eleanor & Cyrus
THE BEST. Technically Eleanor and Cyrus should be number one, because they’re the only genuinely flaw-free couple in the Gossip Girl universe, but their screen time is a little too limited to bag the top spot. Eleanor was a pretty strong contender for world’s worst mother in the first season, but under Cyrus’s adorable influence she became warmer and more supportive towards Blair, while Cyrus himself was basically the perfect stepfather. These two are proof that real love is possible on the Upper East Side.
2. Chuck & Blair
Oh, Chair. So divisive. So inconsistently written. So undeniably hot together. Had Gossip Girl only lasted two seasons, these two would be number one with a bullet – Leighton Meester and Ed Westwick’s chemistry was so off-the-charts that it altered the whole course of the show, right from that first hookup in the back of Chuck’s limo. The relationship became, for better or worse, the centre of Gossip Girl for pretty much its entire run, but a couple of seriously questionable storytelling choices in seasons three and four made their epic romance deeply uncomfortable to watch. Yes, we’re talking about the time Chuck pimped out Blair to his rapey uncle, and that other time he attacked her.
Clearly realizing that they’d gone a little overboard with all the sexy dysfunction, the writers spent the next two seasons trying to rehabilitate Chair. They’re toxic as hell, but that’s par for the course in Gossip Girl, and Chuck’s awful behavior was at least openly acknowledged in the show, so that he had to genuinely change in order to win Blair back. And let’s face it – that chemistry alone has to put them close to the top spot.
1. Serena & Nate
If Serena wasn’t going to end the show single (which she probably should have), her best endgame option by far would have been Nate. These two had a big hand in defining the tone of Gossip Girl – it was their scandalous hookup at the Shepard wedding that started it all – and they always made sense together because they’re essentially the same person: effortlessly gorgeous, insanely loyal social butterflies with a rebellious streak.
Season three was a golden age for GG romances in that everybody was with their best match (Chuck/Blair, Dan/Vanessa and Nate/Serena) and the way Serena and Nate drifted apart afterwards never really added up. Okay, so they weren’t the show’s most compelling pairing, but that relative lack of drama was a breath of fresh air compared to every other messy romance on this list.