Throughout its six seasons, Gossip Girl it had a lot of romantic drama. The core members of the cast went through many relationships, with each other and with a seemingly endless parade of guest stars coming and going with surprising ease.

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Of all the romantic couples, some immediately stood out as the “endgame” couples, the ones who would surely end up together, no matter how many difficulties they had to face before reaching their happy ending. However, some others seemed like a terrible idea from the start and audiences realized they wouldn’t last long.

10 Blair and louis

By the time Blair met Louis, audiences were already too interested in Blair and Chuck’s drama to care about any potential new partners. So when the kind, handsome and passive Prince of Monaco came onto the scene, hardly anyone believed it would be Blair’s happy ending.

This is a romance that went on for too long. Over and over again, it became clear that Blair didn’t love Louis and was only with him because she knew Chuck was bad for her. However, she never really tries to make it work for the Prince and actually treats him pretty bad for the entire duration of the engagement. Of course, Louis turns out to be less than charming himself. This relationship was doomed from the start.

9 Serena and Aaron

From episode one, the show made it clear that Serena and Dan were meant to be together. More importantly, he stuck to that idea, constantly pointing out that Lonely Boy and his blonde muse were each other’s true love, even after they both hurt and betrayed each other in the worst way.

Aaron came onto the scene in season two as one of those romantic interests that exists solely to stop the estranged couple from eventually reuniting. In fact, Serena and Dan spent most of season two in this weird will-they-not-them situation that lasted until the last episode, when they seemingly moved on, except they really didn’t.

8 Rufus and Alison

Alison Humphrey in Gossip Girl

Rufus Humphrey started the series separated from his wife, who was revealed to be in Hudson, living with a man named Alex. She returned to Brookly at Jenny’s request and tried to work on her marriage to Rufus. However, things were too tense between them and the relationship finally ends.

From the moment she returned, it was clear that Alison was never supposed to stay. Rufus’s relationship with Lily had already been heavily hinted at and after the party favors, it was clear that they were still in love with each other. Alison, therefore, had no clear plot purpose and no one was really sad to see her go.

7 Diana and Nate

Diana Payne had a big and overly complicated arc in season five. She was the editor of The viewer who also acted as the manager of an upper-class sex work network. He also worked for William Vanderbilt, while having a tumultuous affair with Nate.

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Diana’s job on the show was primarily to cause some trouble, and in that, she succeeded. However, she was only tagged as a guest star on the show, indicating that she would not be around for long. All of this taken together was enough to doom their relationship even before it began.

6 Olivia and Dan

Like Diana and Nate, it was pretty obvious from the start that Olivia and Dan weren’t meant to last. For starters, Olivia was played by Hilary Duff, another big name who only appeared on the show for a limited time. Second, her character was a movie star who wanted a normal college experience, which didn’t bode well for her romance with Dan.

Things got even more complicated when Dan and Olivia decided to have a threesome with Vanessa, only for Dan to start feeling something for his former friend. Their romance ended abruptly, and rather awkwardly, after Olivia decided to go shoot a movie, ending her college career and her romance with Dan.

5 Lily and bart

Bart Bass Lily van der Woodsen Gossip Girl

Lily and Bart’s relationship was always one of the most sinister on the show. Mainly because Bart was a really horrible man, but mainly because Lily still hadn’t gotten over Rufus. It was always puzzling that she decided to go ahead with her wedding to Bart, but when the oldest Bass apparently died, she was free to pursue a real relationship with Rufus.

Once she got tired of being Lily Humphrey, and after it was revealed that Bart was still alive, she went back to him and resumed their marriage as if nothing had happened. They stayed together, even though she knew he was a terrible human being before he truly died, finally ending the misguided union.

4 Eva and Chuck

After Chuck was shot in Prague, Eva discovered him, who cured and cared for him until he regained health. They began a relationship soon after, with him assuming a new identity because he was understandably embarrassed by the horrible things he did in his past. Finally, he confessed the truth and they both returned to New York.

Like Blair’s entanglement with Louis, Chuck’s affair with Eva was just one device of the plot. The public never really believed that he would stay with the secret French girl, even if she really was a much more positive influence in his life than Blair could be.

3 Serena and Ben

gossip girl serena and ben

Serena’s relationship with Ben has to rank as one of the most questionable dating options in all Gossip Girl. As many fans know, Ben and Serena start dating in season 4. However, red flags arose about this relationship as soon as fans found out about their story. Not only did they discover that the ‘friendship’ started when she was their student at boarding school, but the relationship was further engulfed by false accusations and manipulations.

RELATED: Gossip Girl: Serena’s Boyfriends, Ranked

Serena and Ben’s relationship dragged on for several episodes, despite the fact that almost every character on the show told her what a bad idea it was. Fans were happy when the romance finally ended, even if it meant that Serena would yearn for Dan again.

two Juliet and Nate

gossip girl nate and juliet

And speaking of Ben’s sister Juliet, played by CW star Katie Cassidy, she was the main antagonist during the first half of season four. She got involved in a long and elaborate plan to ruin Serena’s life, infiltrating her life by becoming Nate’s girlfriend. Juliet then proceeded to turn Serena’s friends against her, even getting her kicked out of Columbia.

Because Juliet was more or less a villain, no one expected her romance with Nate to go anywhere, not even after she seemingly redeemed herself from her terrible actions. And even though she really cared about Nate, their relationship was based on a lie and she couldn’t go anywhere.

1 Blair and dan

gossip girl dan and blair

By far the most controversial couple on the show, Blair and Dan remain a topic of debate to this day. His chemistry was first evident in previous seasons, when his love-hate dynamic turned him into an entertaining watch. However, once they got together, fans weren’t exactly sure what to feel.

Their relationship never worked because it was always evident that it would not end well. Chuck was still a big part of Blair’s life and obviously Serena was still in love with Dan. In short, fans really couldn’t invest in a romance that was never going to last. When they finally finish and Blair, unsurprisingly, returns to Chuck, nobody was fazed.

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