Gossip Girl: Popular Couples Ranked

Giovanni Rufino / © The CW / Courtesy Everett Collection

Over its six dramatic seasons, Gossip Girl saw much more than its fair share of break-ups, make-ups, hook-ups and everything in between. Seemingly every major character dated almost every other major character, and while fans tried to keep up, they found themselves loving some of these pairings, and hating others. Obviously, the relationship drama was one of the biggest draws for audiences, and since there was never any telling what twist or turn they were going to take, it had fans hooked! Here are Gossip Girl’s 10 most popular couples ranked from worst to best:

10. Nate and Jenny

Of all the odd, awkward, and unexpected couples on Gossip Girl, Nate and Jenny absolutely topped the list of the most hated by fans. While it was hard to dislike Nate no matter what he did, it was equally as hard to like Jenny, so when the two did wind up together briefly, it felt so wrong. Fans don’t like to remember this relationship because it always seemed like a more big brother and younger sister situation, and luckily things ended because, unsurprisingly, Nate realized just how young and immature Jenny really was.

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9. Dan and Blair

If Nate and Jenny wasn’t awkward enough for fans, Gossip Girl gave them another dose when none other than Dan and Blair decided to hook up. For four seasons, fans watched as the pair disliked each other, but were amicable for the sake of Serena, and gradually grew into friends before becoming something more. When the sparks did begin to fly between the pair in season four, everyone could see there was zero chemistry between the two characters and it was actually difficult to watch.

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8. Nate and Vanessa

Nate Archibald seemingly dated everyone, and that included an on-again, off-again relationship with Dan’s best friend Vanessa. The pair were by no means the worst together, but their romance and relationship was almost always overshadowed by drama and complications of some sort, meaning the two could never really be happy. Unfortunately, while the two were cute together, without all of the distractions and outside influences on their relationship, they were actually super boring and one of the least memorable pairings of them all.

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7. Blair and Prince Louis

Blair had quite a few star-crossed romances in a short period of time and one of the most awful, yet oddly intriguing, was her time spent with Prince Louis. Their romance played out like a bad Hallmark movie, and right from the beginning it was pretty obvious to audiences that it was not going to go well after Blair failed the very first test Louis gave her to see if she would be interested in him if he weren’t a Prince. Their whole relationship was marred by others interfering and, of course, Blair’s unresolved feelings for Chuck, which then made it quite clear that there was never going to be anyone else for Blair no matter how hard she tried.

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6. Lily and Rufus

If the teenagers having dramatic relationships wasn’t enough, one of the worst was between Lily and Rufus. It seems that no couple had more people rooting for them than Rufus and Lily, and the fact they didn’t end up together is still a point of contention for many fans. Not only were they adorable together, their rich history made for an amazing story, not to mention they looked fantastic together. Unfortunately, writers took their story in far too many directions, including the return of their love child, and ruined any hope fans had by ending with Rufus with Lisa Loeb, and Lily with William Baldwin.

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5. Nate and Blair

Nate and Blair were both fantastic, but the problem was audiences were introduced to them while they were still young and, of course, Nate had just cheated on Blair with her best friend. As time went on, it was clear that although they were cute together, it was truly just a first love, and not a forever love, and while they definitely made sense, there was no way they were going to stay together.

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4. Nate and Serena

As two of the most popular and best looking people on the series, many fans would have been quite happy if Nate and Serena would have ended up together. While it was their scandalous hook-up which set the whole tone for the series, they were only actually briefly together, and during that time they were happy and seemed like a good match. It was always clear that Dan and Serena would remain a central relationship, but Nate and Serena made just as good of a match, and to some fans, were even better.

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3. Cyrus and Eleanor

Gossip Girl’s loyal fans had a difficult time when it came to Blair’s mother Eleanor. In the first season it seemed highly unlikely there was going to be any way to actually like the character, but thanks to Cyrus, she actually became very well-liked. In many ways, despite being perhaps the most unlikely or surprising couple on the series, they were actually the best. Despite their differences, they made each other better and most importantly proved to Gossip Girl fans that not every relationship had to be twisted and ruined by drama.

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2. Serena and Dan

A lot of Gossip Girl‘s most loyal fans have mixed feelings when it comes to the central relationship between Serena and Dan. In season one, everyone was rooting for the Upper East Side’s most popular and beautiful girl and the guy from the “wrong side” of the city, and while their make-up and break-up routine got old kind of fast, there was always the hint that they were meant to be together. While a happy ending and a wedding is usually the best way to conclude a series as epic as Gossip Girl was with a relationship that was as dramatic as Serena and Dan’s was, everything was ruined with the knowledge that Dan was in fact Gossip Girl all along. The revelation didn’t make a lot of sense, but at the basis, Dan had essentially stalked, shamed, and humiliated all those closest to him for years, and yet Serena married him anyway. There is no way to be completely happy with that ending.

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1. Chuck and Blair

While the main focus of the show began was on Dan and Serena, it did not take long for Chuck and Blair’s turbulent, and at times twisted, relationship to overshadow all others. Despite many highly questionable storylines between the two, their chemistry was undeniable, and no matter what situation they faced, fans always held out hope that they could make it. What was most important about their relationship was that Chuck was forced to acknowledge his absolutely despicable behavior and had to truly change in order to be with Blair, making them without a doubt the number one couple for most fans.

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Telisa Carter

Telisa Carter

Telisa enjoys learning and writing about all things entertainment in the world of Hollywood. When she isn't catching up on her favorite TV shows, she likes to read, and obsess over all things football.