A television series like Gossip Girl is built on its romantic pairings and scandals. Based on the series of young adult books of the same name, fans watched a group of high schoolers from New York struggle to stay at the top of the social ladder while stabbing one another in the back one week and teaming up the next.
The series produced some of the most iconic pairings for the CW network, but not all of them were the best. In fact, a lot of the show’s major couples were some of the worst in the series. Some couples brought out the worst in one another, while others were downright boring for the audience to watch. Though there were dozens of hook-ups and breakups on Gossip Girl, we’ve tracked every major Gossip Girl couple and ranked them from worst to best.
Blair And Chuck
Chuck and Blair spent most of the Gossip Girl series as the show’s It couple. The audience loved to watch their drama. Just because they entertained us didn’t mean they were a good pairing.
The duo spent most of their time together scheming and trying to one-up each other. It was hard to believe there was real love in their relationship when everything was a competition or a transaction. A writer’s twist at the end of the show had them wind up together all over again—even though they had both already found better matches in the past.
Dan And Georgina
Dan was always presented as the one person with a moral compass on the show. He didn’t scheme his way to the top of social pyramids, and he wasn’t interested in how many people knew his name. Georgina was the exact opposite. The two of them made an odd couple of epic proportions, only together because she tricked him into believing her baby was his. Of course, with the final reveal of the series that Dan was actually Gossip Girl, maybe these two deserved one another.
Dan And Serena
Dan’s crush on Serena kicked off the events of Gossip Girl. They were the ones we were supposed to root for. Good guy Dan should have tempered Serena’s wild child ways. It’s a shame they were so bad for one another.
Like Chuck and Blair, these two brought out the worst in each other. His feelings for Serena turned Dan into a bit of a schemer. While Serena appeared to be a bit more down to earth while they dated, it never lasted long. The fact that the duo married even after the finale revealed Dan as the person who tormented Serena and her friends is also just plain weird.
Nate And Blair
When the series began, the audience thought Nate and Blair would prove themselves to be high school sweethearts. Despite wanting to present a perfect teen couple though, the two never could. Nate cheated on Blair with Serena. Blair cheated on Nate with Chuck. They never seemed to see eye to eye on anything. It’s good that the writers realized these two worked better as friends who could be honest with one another about what they wanted instead of sweethearts who kept lying to one another.
Dan And Vanessa
If Dan and Vanessa had never been dragged into the popular crowd’s inner circle, they might have worked out. Best friends as children, they only briefly dated during the events of the series.
Friends-to-lovers is a fairly common trope in young adult storytelling. Because of that, these two ending up together could have made sense. Outsiders with similar interests, they could have worked. Instead, they first got together after an adventurous night with Dan’s girlfriend Olivia and then kept trying to force a connection that just wasn’t there anymore.
Lily And Rufus
These days, it seems like a prerequisite for the teen love interests in a show to find out their parents dated in the past. In the days of Gossip Girl, though, it was still a fresh surprise. Lily and Rufus reconnecting while Dan and Serena were figuring out their own relationship was not an unwelcome surprise for viewers.
Unlike his son, Rufus didn’t let the trappings of the Upper East Side get to him as easily. Likewise, Lily’s relationship with him actually did seem like it tempered her snobbish side. The two complemented one another much better than most of the other pairings on the show.
Nate And Serena
Yes, Nate and Serena first got together before the events of the series when they hooked up behind Blair’s back. After the friends worked out how wrong that was, though, they had a chance to try a real relationship. These two made one of the more well-adjusted couples on the show. They didn’t have to introduce outlandish antics to keep one another interested. The biggest obstacle to the two of them being a couple was the fact that neither of them could ever seem to let go of their pasts.
Blair And Dan
Given that fans enjoyed watching Chuck and Blair for the drama, the idea of Blair and Dan together didn’t sit well for some. That being said, Blair and Dan had a much healthier relationship once they became allies.
Blair and Dan competed for internships, but they didn’t compete in their love life. Dan was there for Blair during her dreams of being a princess, and to be her getaway driver when they didn’t work out. They had similar taste as well, making them a much better fit than the other young couples in the series.
Eleanor And Cyrus
A rare instance of a genuinely supportive couple in the Gossip Girl universe, Eleanor and Cyrus were always there for one another and their extended family. They had a rocky start to their marriage when Blair attempted to break them up, but she very soon accepted Cyrus as her stepfather.
Cyrus and Eleanor didn’t spend a lot of time on the show because they made the move to Paris while Blair remained in New York. Blair was still able to reach out to them when she needed help, and scandal never followed them like it did the other couples on the show.
Dorota And Vanya
The Gossip Girl writers probably didn’t anticipate Dorota becoming such a popular character when she was first introduced. Originally simply a maid in the Waldorf household, Dorota became Blair’s right hand. Her relationship with a doorman became a popular background story.
Though not a focal point for the stories, Dorota and Vanya dated, married, and had a child while the rest of the characters spent their time fighting and scheming. They had what passed for a fairy tale romance in Gossip Girl, with Vanya calling Dorota a princess that made him feel like a king.