Gossip Girl: 5 Relationships Fans Were Behind (& 5 They Rejected)

Gossip Girl Cast

We all know that the real reason why we tuned into Gossip Girl wasn't just because of the awesome fashion or the campy drama that only a soap opera could provide. It's no secret that the main reason the majority of us tuned into GG was because we wanted to see who would end up with who and which relationships in the drama series would crumble to pieces. Which couples on Gossip Girl were fans obsessed with? Which couples made us want to throw things at the screen? Read on to find out!

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Chuck and Blair, better known by the fandom as "Chair", were pretty much the "it" couple throughout Gossip Girl and they were basically the reason most fans tuned into the series in the first place. Watching their passionate romance unravel with just three small words was the highlight of the series for most viewers and it kept the show alive long after it started to go downhill.

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Chuck and Blair are the definition of a "power couple" because they are both on top of the world and they help each other grow into even stronger versions of themselves - with an added vulnerable side that we never thought we'd see before from these two.


We have seen this trope one too many times before. The gawky writer dude with the man-purse falls for the gorgeous dream girl muse. Anyone else watch Netflix's You? Poor Penn Badgley. Typecasting is real, guys.

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It's nice to think of a writer in love, using his crush as the inspiration for his poems and sonnets, but Dan fails to use Serena as his inspiration for such things that would make Shakespeare proud. Dan has Serena as his muse for a gossip column. One that exists to humiliate others for being human by exposing their darkest secrets to the world- or at least to the Upper East Side. Doesn't sound so romantic, but a little more sociopathic to us.


This was pretty much one of the only relationships on Gossip Girl that offered the potential of a healthy and intellectually stimulating relationship that could last a lifetime. The two had been best friends for life, both extremely comfortable with each other and able to easily talk to one another.

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It wasn't until their threesome with Hilary Duff that Dan and Vanessa were able to see each other in a whole new light and fans were hopeful that Dan would drop his superficial feelings for Serena in order to make things work with his intellectual equal/best friend. It's literally "You Belong With Me" by Taylor Swift. But apparently, the writers decided these two didn't belong together because they wanted to stick with the Dan/Serena endgame and blah blah blah. Point is these two should've ended up together. Who's with us?


This was one of those unfortunate couples that only stayed intact because of the amount of time they had been together. They started dating in kindergarten, which is just... strange. How do toddlers date at this age? Did they share a juice box by the monkey bars? Anyways, it was the fact that they had been together for so long that kept them glued at the hip, along with their families both wanting them to be endgame. It seemed a little bit too perfect and safe which is why Blair ultimately rebelled with Chuck (as Nate did the same with Serena).


This was by far the healthiest (and the cutest) couple in the history of Gossip Girl (and, most likely, the history of any program on The CW Network). Cyrus and Eleanor were perfectly happy with one another because there was no drama or games in their relationship - all they did was lift each other up and feel happy with one another. Doesn't that just make your heart melt? Plus, Cyrus was like the father that Blair never had, and he taught Blair how to be a better person when he had no obligation to do so. He completed the Waldorf family and it changed everything for the better. *Swoons*.


Look, we all know Chuck is supposed to end up with Blair and Fleur Delacour is supposed to end up with Bill Weasley. Why even bother showing scenes that have to do with the evolution of Chuck and Eva when we know they're not gonna end up together? Sure, they have a nice relationship in Paris (filled with lies and deceit because it's Gossip Girl and that seems to be a necessity in relationships according to this universe). But is a "nice relationship" enough? Not in this soap opera, no way. It seems tedious when we see Chuck and Eva "develop" on screen because we know it's not gonna last. Pretty much no one in the world is team "Cheva".


When two people are quite similar it can either make or break a relationship. With Nate and Serena, the fact that they were so similar only worked to make them an even stronger power couple. Both Serena and Nate are conventionally gorgeous, both are kind spirits, and both have the social skills that most of us strive for. Although some might consider their pairing to be somewhat predictable and boring, we know these two would be able to get along just fine and that they'd throw some killer parties together. Nate and Serena just seem so at ease together and drama-free, something that is always rare and refreshing in the world of Gossip Girl.


So this relationship is just plain problematic on like a thousand different levels, mostly due to the fact that the actors had such a significant age difference between them while filming. News Flash Gossip Girl writers, this is a teen series, not Lolita. At the start of the show, Taylor Momsen who plays Jenny was fourteen-years-old while Chase Crawford was twenty-two. We were half expecting Chris Hansen to appear during their scenes together and it just made us uncomfortable to watch. On the subject, Crawford himself had this to say: "I always thought (Nate and Jenny) was a little weird. There's the age gap, she's still in high school..." We agree with you, buddy.


Lily and Rufus were easily one of the most romantic couples on the show because of how much Rufus loved this woman. We were all rooting for them to finally have their fairytale happy ending because although they didn't seem like a conventional match, their feelings for each other overpowered social status. Unfortunately, they never got the chance to have their happily ever after because the writers apparently wanted to play with our hearts, but it seems as though the actors who play Lily and Rufus were rumored to be dating in real life. How cute!


We know what you might be thinking. "Who the hell is Tripp?". Let us refresh your memory. Tripp Vanderbilt (his actual name- we couldn't make this up) was Serena's lover towards the beginning of the series. He may be a fully grown adult with a full-time job along with a wife, but that doesn't stop this chump from lusting after a sixteen-year-old girl. Gossip Girl is a whole lot more messed up than most of us remember it being as teens. How was this relationship ever allowed? Genuinely curious.

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