Like many teen shows that came before it, Gossip Girl had its fair share of scandal and drama. When the characters weren't scheming to get what they wanted on the luxurious Upper East Side, they were falling in and out of love with one another.
The show had an abundance of relationships that kept fans on their toes, wondering what will happen next and if their favorites will become endgame. With six seasons in total, the show featured a lot of different pairings. While some were excellent matches, others were just totally wrong for each other, going on to become some of the worst couples in Gossip Girl history.
Season 1: Nate & Blair
During the first season of Gossip Girl, the love triangle between Blair, Chuck, and Nate takes place. At the start of the series, it's established that Nate and Blair have been dating for a while. Their families even had high hopes for them and put pressure on their relationship to move forward. After it's revealed that Nate lost his virginity to Serena while still with Blair, their relationship is tarnished.
If Nate's cheating doesn't make it clear enough, as the season progresses fans realize that the two simply do not belong together because they are very different people. What kept them together was outside forces that told them they were meant to be. Although Blair and Nate date later on in the series, they break up again because they realize their time together came and went. They know that they are better off as friends (or their own version of friends, at least), and their relationship ups and downs, particularly in season 1, prove this.
Season 2: Catherine & Nate
The second season of Gossip Girl begins with Nate and Catherine's affair. Of course, this relationship is very short-lived, thankfully. The age difference was uncomfortable, and so was the fact that Catherine was only using Nate to cheat on her husband. It only got even messier when Blair, Nate's ex-girlfriend, started dating Catherine's stepson, Marcus.
Essentially, Nate was taken advantage of by Catherine, and, for his part, he never truly had real feelings for her. Since their relationship was mainly physical, there wasn't time to develop any true substance, particularly because Catherine didn't want to divorce her husband. They were a Gossip Girl relationship fans knew were doomed from the start and surely the worst in season 2.
Season 3: Dan & Olivia
Dan and Olivia's romantic relationship starts out very innocent and sweet but quickly comes to an end within the same season. Their relationship involved a lot of jealousy and trust issues, mainly on Dan's side since Olivia, played by Hilary Duff, was in the public eye.
Things become more complicated when the pair have a threesome with Dan's longtime best friend, Vanessa, for whom he already had feelings. Putting Olivia in the middle of that was unfair and a bad move and causes their relationship to sour. In addition, their whole relationship is based on a lie when Olivia isn't honest with Dan about who she really is. At the time it made sense for her to not overwhelm Dan, but relationships that begin with a lie never really stand a chance.
Season 4: Chuck & Eva
After Chuck is left shot in an alley he's essentially rescued by Eva. Eva is nothing like the kind of girls Chuck knows back in Manhattan, and this is what draws him to her. Ultimately, the pair doesn't work because Chuck is not really himself when he's with Eva. Although he actually proves to be a better version of himself, thanks to her bringing out good qualities in him, it's clear he doesn't have long-lasting, deep feelings for her. This is particularly obvious when fans that, just one season before, Chuck planned to propose to Blair.
In addition, Eva is just not equipped to handle the fast-paced life of the Upper East Side. She even mentions that Chuck's life is too much for her and she is not up for scheming and plotting, which are ultimately the things that Chuck is best at. On top of all of that, while Chuck and Blair do bad things to each other, fans know by this point in the series that they're endgame.
Season 5: Blair & Louis
After Blair and Chuck called it quits in season 3, Blair meet a French Prince named Louis. Their relationship seems fine in the beginning until they actually start to get to know each other. Blair and Louis should have never got engaged from the start. Throughout their relationship, Blair seems to only care about her peers and how they are reacting to the fact that she is with a prince.
Blair still had strong feelings for Chuck and was simply using Louis for his status as a prince. Louis and his family also made sure that the couple wouldn't work by constantly giving her a hard time and it was difficult to watch Blair, known for her savage quotes and feisty personality, put up with that kind of behavior. Things got even worse when they actually got married and Louis showed who he really was.
Season 6: Nate & Sage
Although there were many strange couplings in this final outing, Nate and Sage take the prize for the worst ship in season 6. The obvious problem with them as a couple was that he was an adult and she was only a teenager when they began dating. They also didn't have much chemistry or really anything in common for them to be a couple worth rooting for.
Nate has had many girlfriends and love interests that go against most people's morals and the acceptable status quo, but his romance with Sage is perhaps the worst. When the show later reveals that Sage's father is dating Serena, Nate's ex, things become even creepier.