During the six seasons of Gossip Girl, there have been dozens of relationships that have made us cringe or made us say aw and in light of the new reboot out on HBO Max, we thought it was the perfect time to break down the best and worst Gossip Girl couples in no particular order.
Best: Serena and Nate
Everyone can agree that Serena and Nate were always a perfect match: both stunning, outgoing social butterflies with an edge of rebellion. Their scandalous hookup at the Shepherd wedding was what started it all, and from then everyone knew the two had an unspoken attraction towards each other. It is extremely disappointing that the two never reignited their evident spark after Blair had clearly moved on. If their effortless and fun chemistry is not enough to convince you, their magnificent locks will; their golden blonde hair complements each other flawlessly! You may not agree they were the best couple, but they were certainly among the prettier Gossip Girl couples.
Worst: Dan and Blair
This next one is definitely one of the more confusing Gossip Girl couples; many people have different opinions on Dan and Blair. The idea of the two dating after a rocky relationship of bickering amongst each other is cute in other situations, but when it comes to Dan and Blair it was just weird. None of it made sense and it was unsettling to see Blair, the queen of style and chic class, with Dan who lacked flair and polish. We think the friendship they formed as they got to know each other and realized they could get along if they tried was sweet but ultimately wrecked when they decided to add actual feelings for each other. Blair and Dan together just felt wrong on so many levels, and we just wish they had stayed as friends instead of forming a relationship that no one wanted to see.
Best: Rufus and Lily
Rufus and Lily have the ideal love story: she lives on the Upper East Side and he lives in Brooklyn; she dresses in strictly designer clothes and he dresses in the same outfit every day. Their connection defied logic while simultaneously making perfect sense; the best part was that they were each other’s first loves who, despite marrying other people in between, always found their way back to each other. In some ways, they were amongst one of the more genuine Gossip Girl couples; they were constantly bickering and never seeing eye to eye, but they still managed to love each other despite everything. Unfortunately, the two were not endgame, which we are still salty about, but we like to assume that they found their way back to each other after the show ended.
Worst: Blair and Louis
This is without a doubt one of the worst Gossip Girl couples of all time. For one thing, Blair and Louis’ relationship was preventing Blair from being with Chuck, which was a major no-no. Apart from that, the situation as a whole was fishy, and we did not enjoy seeing our Blair caught up in all the machinations and drama; she had enough on her plate as it is, and Louis and his family were deceitful and meddled far too much. Although we can admit that the downfall of their relationship was not solely on Louis, Blair was at fault in many of her own ways which only proved more that she did not really want to be with him. Then there was Beatrice, Louis’ sister, who only added fuel to the fire and irritated us to no end. The bottom line is, Blair is already the queen of the Upper East Side, she does not need to marry a prince!
Best: Chuck and Blair
Would this even be a rundown of Gossip Girl couples if Chuck and Blair weren’t mentioned? The chemistry between the two was undeniable and it really came to life whenever the two were on screen together. Although their relationship was obviously drama-filled and at times incredibly toxic (i.e. Chuck attempting to sell Blair for a hotel, a million breakups and revenge hookups, etc.) It was still the most iconic and memorable pairing of the entire show. The characters’ growth as they go through relationships with different characters and always find their way back to each other is something that viewers can’t help but yearn to follow to know what will happen next between the two. The fact that Chuck and Blair are so similar in their planning and propensity to do whatever it takes to achieve what they want is maybe the best part about their relationship; the two are able to be entirely and utterly themselves with one another and have a lot of fun doing so. Not to mention Chuck’s growth as a character, who was clearly pushed by his affections for Blair to mature and face his feelings, becoming a more mature version of his deceitful self. Overall, viewers are aware that Chuck and Blair’s relationship is impossibly wild, but that is precisely what makes it so beautiful and suspenseful!
Worst: Jenny and Anyone
We apologize in advance to anyone who does not enjoy Jenny slander, for that is exactly what this is. Jenny has produced some of the worst of Gossip Girl couples, whether it was with Nate, Chuck, or anyone else she met, even if they didn’t date. Jenny’s decision to give up her virginity to Chuck after he attempted to sexually attack her in season one is strange, stupid, and stomach-churning. There’s not much else to say except that no matter who Jenny was with, it always ended in some type of unnecessary drama that even those of us who enjoy a little stir in the pot find absurd.
Best: Eric and Jonathan
We wish we had seen more of Jeric, despite the fact that these two were mostly background characters. The couple was as drama-free as any Gossip Girl couple could be while also being unquestionably cute! Eric’s first serious relationship was with Jonathan, and they were together for a long period before Jenny, as per usual, ruined everything. Eric’s happiness with someone, as well as good LGBTQ representation, was a sweet thing to see for the audience! Unfortunately, Eric does not appear to receive as much credit in the show as he deserves, which we hold against the producers.
Worst: Vanessa and Anyone
Much like Little J, anyone Vanessa has been with also seems to fall under the worst Gossip Girl couples category! She tried with Dan, Dan’s long-lost secret half-brother, Nate, and even hooked up with Chuck at one point. Every time she tries with anyone, Vanessa ends up ruining it with some sort of weird scheme or by budding into business she just does not belong in constantly. The worst part is, Vanessa thinks that she is too good for the Upper East Side and has to make it very clear to everyone. In her defense, I believe she and Dan had the most in common and had the potential to work out, but the Gossip Girl writers botched that one. For the time being, let’s just say Vanessa was incompatible with everyone on the show.
Best: Carter and Serena
Despite the fact that Serena and Carter had a brief romance, we can’t help but like their connection. Their adventurous escapades together in pursuit of Serena’s father all around the world demonstrate how much fun they had together and how natural their connection was. Maybe we are biased because of how good the two looked together on TV, but we honestly believe Serena and Carter had chemistry, even if it was only a smidgeon.
Worst: Rufus and Ivy
We are truly sorry that we have to make you relive this one, but it is simply too revolting and perplexing not to. I’d like to sit down and have a long chat with whoever thought this was a good idea, and I’d like them to apologize for nausea I experienced as a result. All I have to say is that this should never, ever happen again, or at the very least, Dan should not have to witness it. Bottom line: We’re never going to talk about this one again.