Throughout the course of its six seasons, Gossip Girl had a lot of romantic drama. The core members of the cast went through a lot of relationships, with each other and with a seemingly never-ending parade of guest stars who came and went with surprising ease.
Out of all the romantic pairings, some immediately stood out as the "endgame" couples, those that would surely end up together, no matter how much hardship they had to face before they reached their happy ending. However, some others seemed like a terrible idea from the start and audiences could tell they wouldn't last very long.
Blair & Louis
By the time Blair met Louis, audiences were already too invested in the Blair and Chuck drama to care about any new potential partner. So when the kind, handsome, passive Prince of Monaco came into the picture, pretty much no one believed he would be Blair's happy ending.
This is a romance that dragged for too long. Time and again, it was made 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 with the Prince and actually treats him pretty badly for the entire duration of the engagement. Of course, Louis turns out to be less than charming himself. This relationship was doomed from the beginning.
Serena & Aaron
From episode one, the show made it clear that Serena and Dan were meant to be together. Most importantly, it stuck to that idea, constantly signaling 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 of ways.
Aaron came into the picture in season two as one of those romantic interests that solely exist to stall the eventual reunion of the separated couple. Indeed, Serena and Dan spent most of season two in this weird will-they-won't-they situation that extended to the very last episode, when they seemingly moved on, except they really didn't.
Rufus & Alison
Rufus Humphrey started the series separated from his wife, who was revealed to be in Hudson, shacking up 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 strained between them and the relationship ultimately ends.
From the moment she returned, it was clear that Alison was never meant to stay. Rufus's relationship with Lily had already been heavily hinted and after cotillion, it was clear they were still in love with each other. Alison, therefore, had no clear purpose on the plot and no one was really sad to see her go.
Diana & Nate
Diana Payne had a major, overly convoluted arc in the fifth season. She was the editor of The Spectator who also acted as the manager of a high-class sex-work ring. She was also working for William Vanderbilt, all while having a tumultuous affair with Nate.
Diana's job in the show was mainly to cause some trouble, and at that, she succeeded. However, she was only ever labeled as a guest star on the show indicating she was not going to be around long-term. All of this together was enough to doom their relationship before it even began.
Olivia & Dan
Similar to Diana and Nate, it was pretty obvious from the start that Olivia and Dan weren't really meant to last. For starters, Olivia was played by Hilary Duff, another big name who was only appearing in the show for a limited time. Secondly, her character was a movie star who wanted to have a normal college experience, which didn't bode well for her romance with Dan.
Things grew even more complicated when Dan and Olivia decided to have a threesome with Vanessa, only for Dan to start having feelings for his former friend. Their affair ended abruptly, and rather uncomfortably, after Olivia decided to go shoot a movie, effectively ending both her college career and her romance with Dan.
Lily & Bart
Lily and Bart's relationship was always one of the most sinister of the show. Mainly because Bart was a really awful man, but mostly because Lily was still not over Rufus. It was always puzzling that she decided to go on with her wedding to Bart, but when the elder Bass seemingly died, she was free to pursue a real relationship with Rufus.
Once she got tired of being Lily Humphrey, and after Bart was revealed to still be alive, she went back to him and resumed their marriage as if nothing happened. They stayed together, despite her knowing that he was a terrible human being before he died for real, finally putting an end to the misconceived union.
Eva & Chuck
After Chuck was shot in Prague, he was discovered by Eva, who healed and nursed him back to health. They started a relationship soon after, with him assuming a new identity because he understandably felt ashamed about the horrible things he did in his past. He eventually confessed the truth to her and they both returned to New York.
Like Blair's entanglement with Louis, Chuck's affair with Eva was just a plot device. Audiences never really believed he would stay with the secretive French girl, even if she indeed was a much more positive influence in his life than Blair could ever be.
Serena & Ben
Serena's relationship with Ben has to rank as one of the most questionable dating choices in all of Gossip Girl. As many fans know, Ben and Serena start dating in season 4. However, red flags about this relationship were raised as soon as fans learned of their history. Not only did they discover that the 'friendship' start when she was his student at boarding school, but the relationship was further enmired with false accusations and manipulations.
Serena and Ben's liaison went on for several episodes, despite nearly every character in the show telling her just how bad an idea it was. Fans were happy when the romance finally ended, even if it meant that Serena would go back to pining for Dan.
Juliet & Nate
And speaking of Ben's sister, Juliet, played by CW staple Katie Cassidy, was the main antagonist during the first half of season four. She engaged in a long and elaborate plan to ruin Serena's life, sneaking into her life by becoming Nate's girlfriend. Juliet then proceeded to turn Serena's friends against her, even succeeding in getting her kicked out of Columbia.
Because Juliet was pretty much a villain, no one actually expected her romance with Nate to go anywhere, not even after she was seemingly redeemed of her terrible actions. And while she really cared for Nate, their relationship was based on a lie and couldn't go anywhere.
Blair & Dan
By far the most controversial pairing in the show, Blair and Dan are still a subject of debate to this day. Their chemistry first became apparent in the earlier seasons, when their love-hate dynamic made for an entertaining watch. However, once they actually got together, fans weren't exactly sure what to feel.
Their relationship never worked because it was always apparent that it wouldn't end well. Chuck was still a big part of Blair's life, and Serena was very obviously still in love with Dan. In short, fans couldn't really get invested in a romance that was never going to last. When they finally break up and Blair unsurprisingly goes back to Chuck, no one even batted an eye.