Many relationships started and ended throughout Gossip Girl's six seasons. It's safe to say that our favorite Upper East Siders dated around quite a bit. Some of these couples were beloved by fans and some just made viewers uncomfortable.

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Dan and Serena's relationship, for instance, was one that fans endured for far too long. On the other hand, viewers loved watching Cyrus and Eleanor's relationship blossom. Keep reading to find out the five unhealthiest and five most wholesome relationships from the series.

Unhealthy: Nate And Blair

These two were together for all the wrong reasons. According to Chuck, Nate and Blair had been together since grade school and their parents wanted them to get married. It seems they both fell into what was comfortable and waited far too long to question their relationship.

Nate was in love with Serena and Blair was only in love with the idea of Nate. Luckily, they recognized this early on in the series and called it quits.

Wholesome: Chuck And Blair

gossip girl chuck blair

It's no secret that this couple had their fair share of problems. They had the odds stacked against them from the start but as the series progressed, these two grew together in a beautiful way.

Chuck and Blair endlessly supported and loved one another and this was exemplified in the series finale when they eloped in Central Park. While it's true that they got married in order to achieve "spousal privilege," it was still pretty romantic.

Unhealthy: Dan And Serena

serena dan gossip girl

Time and time again, Serena and Dan found themselves giving their relationship a second chance, but neither one of them deserved it. Both of these characters were horrible to one another.

Dan endlessly manipulated Serena and spread lies about her as Gossip Girl while Serena took Dan for granted and refused to fully let him into her life. These two just couldn't get it together, but somehow ended up married by the series finale.

Wholesome: Cyrus And Eleanor

Cyrus absolutely is Eleanor's perfect match. At the beginning of the series, Eleanor came off as cold and heartless -- especially to Blair. However, her heart seemed to soften as soon as she got together with Cyrus in season two.

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It's impossible to not like Cyrus, he even managed to win Blair over in the end. Fans loved these two together and witnessing Blair get the present father figure she deserved was just the cherry on top.

Unhealthy: Dan And Georgina

Georgina Sparks smiling at Serena in Gossip Girl

It's not a healthy relationship as long as Georgina Sparks is involved. While Georgina had a few redeeming qualities, she was mostly the villain of the series.

Georgina went to great lengths to cause drama in our favorite Upper East Siders' lives including lying about her identity and tricking Dan into taking care of her child. Dan and Georgina got together on a number of occasions and fans squirmed each time.

Wholesome: Dan And Vanessa

Time wasn't on Dan and Vanessa's side and unfortunately, these two didn't end up together. It's a shame considering they were truly perfect for one another.

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Before Dan became obsessed with the Upper East Side, he and Vanessa were best friends and even on the verge of becoming a couple. If only Dan had let Serena go, Dan and Vanessa would have lived happily ever after in Brooklyn.

Unhealthy: Nate And Jenny

Nate and Jenny talking in Gossip Girl

Many fans wish that these two had never gotten romantically involved. While it's true that Nate is a good guy and has always been there for Jenny, he's made it clear that he sees himself as a big brother figure.

Their platonic relationship was endearing but their romantic relationship was uncomfortable. These two had very little chemistry and Jenny wasn't in a good headspace when they gave things a shot in season two.

Wholesome: Lily And Rufus

Lily, Rufus and Scott meet in Gossip GIrl.

It seems as though these two were meant to be from the very beginning. Fans loved seeing their relationship blossom and watching the Humphreys and the van der Woodsens become a family.

Not only did Rufus and Lily have a strong joint family, but they also shared a son who they finally met in season three. It's a shame that this pair didn't end up together in the long run.

Unhealthy: Blair And Louis

Blair wanted to be with Louis for all the wrong reasons. She loved that he was a prince and she let herself get wrapped up in a fairytale - even though she was truly in love with Chuck.

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When the truth came out about Blair's love for Chuck, Louis became the series villain and made Blair's life miserable. It's safe to say that this relationship was one big mistake.

Wholesome: Dan And Blair

Blair and Dan standing together and smiling on Gossip Girl

This relationship definitely came as a surprise to fans. Dan and Blair came from different worlds but had more similarities than they wanted to admit.

Viewers saw plenty of chemistry between these two when they finally got together in season five. They brought out the best in each other and bonded over their mutual love for books, movies, and art. Unfortunately, they eventually called it quits, but their relationship was great while it lasted.

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