Gossip Girl: Who Each Main Character Should've Ended Up With

Even years after it's ended, Gossip Girl continues to be a widely controversial television show. There are plenty of aspects about the series that aged poorly, but viewers appear to be the most divided over the characters and their relationships. Corruption was a main theme of the drama, but it extended far beyond the scope of power and class.

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Chuck and Blair are the central couple of the series, yet they continuously worked against each other and valued status over their relationship. Due to the rumors that were spread and the multiple betrayals within the friend group, it's hard to find a truly healthy couple in Gossip Girl. However, most of the characters should've ended up with someone other than who they did.

6 Vanessa Abrams: Olivia Burke

Vanessa didn't have a lot of luck in the romance department, and none of her relationships had viewers invested enough to root for. In fact, there are several times fans felt bad for Vanessa in Gossip Girl, and her character deserved a better storyline than she got. She ended up in a love triangle with Dan and his girlfriend Olivia, but Vanessa and Olivia had far more chemistry than either woman had with him.

Olivia was only around for a short while, as she abruptly exited the show after Dan left her for Vanessa. Olivia was the only person Vanessa shared any kind of spark with, and the series would've been better off exploring a romance between them rather than throwing Dan into short-term relationships with them both.

5 Jenny Humphrey: No One

Jenna started the series as the sweetest and most humble character, but her desire to be friends with Blair and join the popular clique made her flat-out unlikeable. None of Jenny's relationships felt genuine, and she had no sense of loyalty to her friends or her family. Jenny had to work on herself before she could be a good partner to someone, and, ultimately, that's what she did when she left Manhattan.

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However, viewers never got much of a glimpse into her new life, and whether or not there was someone special in it is irrelevant. Jenny never needed someone else to complete her. What she needed was to recognize that what she thought of herself was more important than the validation of others.

4 Blair Waldorf: Dan Humphrey

Out of all of the best Dan and Blair quotes in Gossip Girl, "We're a team" best summarizes their relationship. They were equals in every way and managed to have the healthiest and most entertaining dynamic on the series. The slow burn "enemies to best friends to lovers" aspect of their romance was especially appealing.

There were times when it felt as though the pair was out of a rom-com rather than a teen drama, and many viewers believe that their unexpected relationship is the best part of the series. Both of them had outgrown their previous love interests, and it would've been much more impactful if Dan and Blair had ended up together.

3 Rufus Humphrey: Lily Van Der Woodsen

Rufus and Lily were painted out to be star-crossed lovers from day one. Lily had broken off their relationship years before the pilot after Cece threatened to take away her inheritance if they continued to see each other. As adults, Rufus and Lily faced even more complications, but viewers always thought they would come out stronger on the other side.

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Lily ending up with Serena's father felt like a disservice to her relationship with Rufus, and it's clear that it only happened so Dan and Serena could get married. Given all the deceitful things Dan did to Serena as Gossip Girl, as well as the lengths she went to in order to sabotage his relationship with Blair, their endgame wasn't worth sacrificing what Lily and Rufus had built.

2 Chuck Bass: No One

It's no secret that there's a long list of things about Chuck that would never fly today in Gossip Girl. He attempted to sexually assault two main characters in the first episode, sold Blair to his uncle, and even physically hurt his girlfriend in a fit of jealousy.

Sadly, Chuck is rewarded for his behavior rather than forced to pay for his crimes. His ideal ending would involve a jail cell and a lot of time to reflect on his actions. Chuck has proved multiple times that women aren't safe in his presence, so he should have been locked up far away from them.

1 Serena Van Der Woodsen: Nate Archibald

Nate and Serena remain a fan-favorite pairing in Gossip Girl. No one ever loved Serena as much as Nate, and their relationship came naturally. The two had been friends forever, and if Nate and Blair hadn't dated for so long, it's likely that he and Serena would have gotten together much sooner than they did.

Their relationship was built on infidelity, but they both grew and evolved over the course of the show. By the time Nate and Serena became an official couple, they were two completely different people. Dan never appeared to be very interested in Serena after he fell in love with Blair, and it would've made more sense for Serena to marry Nate instead.

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