Gossip Girl was a popular teen drama series that aired on The CW from 2007 to 2012. The show helped make the network what it is today and has remained topical all these years after its series finale. The series will even get a reboot on HBO Max sometime next year.
One of the biggest draws to Gossip Girl was its many scandalous romances. It seems like every character on the show dated each other at least once. The following list details some of the couples we think would have been great together had they ever gotten together.
Blair & Tripp
Tripp Van Der Bilt was the cousin of Nate Archibald. In the series, he was an ambitious and politically-minded young man who eventually got into a relationship with Serena. Tripp certainly had a dark side as he ultimately became obsessed with Serena and even got her into a car crash.
However, Tripp and Blair may have been better suited to one another. Blair understands the word of mind games and politics much more than Serena ever did. She and Tripp would have understood each other better, almost similar to the relationship Blair has with Chuck.
Chuck & Ivy
Ivy and Chuck would have been an exciting couple to see explored in the series. Ivy came from a very different background from the majority of the other characters. She wasn’t born into glitz and glamor.
However, her rough upbringing gave her some survival skills that she needed while trying to understand the convoluted world she got herself into with the Rhodes family. She may have been able to ground Chuck in some ways. Plus, she helped him out on more than one occasion.
Raina & Dan
Raina Thorpe entered the show in Season 4 and caused quite the stir between main characters Chuck Bass and Nate Archibald. Most characters on the series would eventually date every leading character at least once. Surprisingly, she never dated Dan.
The two would have made an interesting pair since Raina is so strategic, and we know that Dan is too. She’s also very strong and could have helped curtail Dan’s wilder antics.
Nate & Jenny
Nate and Jenny had a lot of romantic tension between them and even shared a kiss at one point, but they never really got a genuine chance to become a couple. Jenny was too immature during the beginning of the series, and her crush on Nate was unrequited because of his feelings for Serena.
Even though they shared a few sweet moments throughout the early seasons, Nate and Jenny never became a legitimate couple. It would have been nice to see them get a chance at it when Jenny had grown up more, and Nate too, for that matter. Had Taylor Momsen not left the show, perhaps it would have happened.
Chuck & Dan
Even though Chuck and Dan are enemies in the literal sense and romantic rivals when it comes to Blair, there are a lot of people in the Gossip Girl fandom who feel the two characters shared a fair amount of homoerotic tension. There were plenty of scenes between them where it seemed like they were on the verge of throwing punches or throwing each other up against the wall for a passionate makeout session.
Needless to say, if Gossip Girl had included gay characters back then or at least made Chuck open to experimenting with his sexuality (as he did in the books), this could have been a fascinating pairing.
Juliet & Georgina
Not many fans remember Juliet Sharp as she was a brief recurring character that entered the show to shake things up for Serena. Whereas Georgina Sparks is a wrecking ball that consistently blows through town to shake things up for every character.
It would have been interesting to see Juliet and Georgina get into a relationship; it certainly would have ruffled some feathers and raised the stakes on the show’s never-ending drama. Plus, both Juliet and Georgina had personal vendettas against Serena.
Georgina & Chuck
Before Georgina came around, Chuck was one of the primary antagonists on the series. He caused a lot of problems in the first season before gradually becoming one of the main characters and achieving some real character development.
There are a great many fans who think Chuck and Georgina would have been a blast to watch on-screen. It helps that canonically, Georgina supposedly took Chuck’s virginity at some point before the series began. There is a mutual attraction between them. Unfortunately, we never get to see it play out on-screen.
Chuck & Juliet
Again, sometimes it’s fun to watch antagonists get together. By the time Juliet entered the scene, Chuck had progressed to being a main character. It’s not likely that he and Juliet would have gotten together during Katie Cassidy’s time on the show.
However, it would have been interesting to see her make a return years later. Imagine if Chuck had walked into town with Juliet on his arm. That certainly would have sent Gossip Girl into a tizzy and created some backlash amongst the gang!
Nate & Dan
Dan and Nate would make even more sense than Dan and Chuck. Dan and Nate genuinely liked each other, most of the time anyway. The two became good friends throughout the series, which only strengthened their pairing. While they had their ups and downs, Dan and Nate were supportive of one another, and they liked to spend time together.
It would have been sweet to see them romantically involved, mainly because they were often so caught up in the romantic drama, often to the point of utter exhaustion. Sadly, this was never meant to be.
Blair & Serena
Out of all the couples never happened, the one that makes the most sense is Blair and Serena. The books hinted, multiple times, that the two best friends had been intimate with one another on more than one occasion.
At the end of the series, they even say goodbye to Nate and start the next chapter of their lives without any boyfriends, just each other. Blair got emotional at the beginning of the series because Serena left her, and some of the constant jealousy between the two girls can easily read as latent romantic feelings.
Next: Gossip Girl: 5 Best Rivalries (& 5 That Made No Sense)
