Gossip Girl: 10 Friendships That Should Have Happened (But Never Did)
Gossip Girl was all about relationships, but there are still plenty of friendships that had tremendous potential but never got to happen.
Gossip Girl is, at its core, all about interpersonal relationships. Whether romantic, platonic, or familial, Gossip Girl created as many relationships as possible, as complicated as possible, and that's where all the fun and drama come from.
However, over the years, narrative necessity meant some interesting potential relationships never got to see the light of day, especially as certain plots never got the attention they deserved.
10 Blair and Eric
With Eric and Jenny occupying the ‘younger generation’ of the Upper East Side for a time, Eric was primarily wrapped up with her and her various schemes, while Blair was of course focused on her own status and her own best friends. That being said, it’s not uncommon in the real world for two best friends to have some kind of relationship with each other’s siblings, and with Eric being Serena’s younger brother, it would have been interesting to see how they were able to affect each other.
They likely could have supported each other, especially while Serena was away, and Eric potentially could’ve been the good influence for Blair that he was for Jenny.
9 Juliet and Georgina
There’s nothing better than two bad guys teaming up, especially when they’re actually bad girls. Both Juliet and Georgina took all sorts of pleasure in tormenting the Upper East Siders, and neither was afraid of fully committing to their often-complicated plans.
Their unique positions in relation to the main cast would have made them unstoppable - Georgina knew them too well, while Juliet offered an outsider’s vantage point, allowing her to pick up on weaknesses Georgina was too close to see.
8 Nate and Eric
Eric suffered from not having much in the way of male role models, and Nate seems like the sort of guy who could get deeply invested in someone else’s success, especially when he saw himself as the main contributing factor to that success.
It would have made sense, especially during the period where Nate and Serena were dating, to show the boys connecting as friends.
7 Vanessa and Serena
Vanessa was pretty much constantly an agent of chaos, foiling most if not all of the main bunch’s plans at one point or another. However, in a different world (where no boys got between them), Vanessa and Serena could have been friends.
Maybe even best friends, given how much they have in common. If they weren’t on the Upper East Side, or maybe just if Serena were in a slightly different position, the two artistic free spirits could have been a force to be reckoned with.
6 Ivy and Blair
While Ivy Dickens was more a tool of an evil genius than an evil genius in her own right, Blair could have taken Ivy under her wing and showed her how to really get what she wanted.
If Ivy hadn’t spent so much time trying to ruin all of the main characters’ lives, there could have been a non-zero chance that Blair would have recognized Ivy as a possible protege, similar to the way she ‘helped’ Jenny.
5 Jenny and Blair
Jenny and Blair had a complicated relationship. Jenny both hated Blair and wanted to be her, while Blair saw her as either an amusement, an annoyance, or - in the end - a suitable successor.
If Blair hadn’t been quite so hard on Jenny, and if Jenny had been either less underhanded or even more devious, they could have had an interesting, if fraught, friendship, sort of like an even more complicated version of Blair and Serena.
4 Scott and the Humphreys
Scott wasn’t on the show for long, which is a shame, considering just how fascinating his relationships with the main cast could’ve been. As the illegitimate son of Lily Van Der Woodsen, Serena’s mother, and Rufus Humphrey, Dan’s father, Scott had a significant connection to several members of the Upper East Side.
We do see him briefly interact with all of his biological family, but it’s the last time he appears in the series. He had a connection with Dan and Rufus over the creative arts - admiring Dan’s writing and having some natural musical ability of his own - and could have been a role model and safe person for Jenny to confide in if she’d stayed on as a regular character.
3 Scott and the Van Der Woodsens
While the focus on Scott is more heavily tied to the Humphreys, that just makes the missed opportunities with the Van Der Woodsens even more disappointing. Serena and Eric have a brother they never knew about, and there’s never much mention of how they take the news, or what relationship they have with him.
Both Serena and Eric could have benefited from an outside support system, especially someone who shares their DNA but not their upbringing. Scott could have helped them really learn how messed up some parts of the Upper East Side are, and maybe even eventually helped them to disengage from it.
2 Scott and Literally Everyone
While Chuck knew who Scott Rosson was from fairly early on, the rest of the gang was more or less kept in the dark (except Vanessa). Nate and Blair could have had an opportunity to be real friends for Eric, Jenny, Dan, and Serena upon the revelation, and it would have been interesting to see if and how Scott was able to be brought into the Upper East Side fold.
While he and Chuck likely would never be destined to be best friends, it would have been fun to have another boy almost as conniving to help keep Chuck on his toes.
1 Carter Baizen and Ben Donovan
Bad boys pairing up is always fun to watch. Because Carter Baizen and Ben Donovan weren’t around in the same seasons, they never had an opportunity to interact. If they had, though, they would have found they had plenty in common - both interested in Serena, both with ulterior motives, both trying to get access to the wider Upper East Side world.
Their motives were different - a necessity for Carter and revenge for Ben - but if they’d existed at the same time, they could have had a truly daunting bad-guy ‘good cop/bad cop’ arrangement, which could have exponentially improved their individual success.