Without doomed romance, there would be no Gossip Girl. The whole show operates around scandals, miscommunications, libelous rampages, and the broken hearts of the ultra-wealthy. If everyone’s relationships were healthy and unremarkable, there would simply be nothing for the anonymous blogger to remark upon.
Looking back across all six seasons, it’s remarkable how many different pairings the creators pulled out of what’s a relatively small cast, creating a mix-and-match of dysfunctional dating partners that includes friends-to-lovers, enemies-to-lovers, and everything in between. Underneath the showy facade of debutante balls and fashion shows, Gossip Girl is ultimately a drama about the negotiation of power within intimate relationships. In this way, the old adage that “knowledge is power” rings true; secrets revealed and lies stacked on top of one another are what produce both monumental fallouts from social grace and moments of so-called outsiders, like Jenny Humphrey or Vanessa Abrams, gaining a foothold in the champagne world of the ruling class.
While this summer will usher in a new iteration of the franchise, there’s no denying that the fresh take will come with a lot of cultural baggage. This refresher summarizes just how twisted, disastrous, and down-right doomed some of the original pairings got.
13. Blair Waldorf & Dan Humphrey
As far as Gossip Girl romances go, there’s really no such thing as being entirely not doomed. But, when looking at short-lived love affairs, there’s nothing quite as wholesome as “Dair.” This enemies-to-friends-to-momentary-lovers progression is truly the only relationship on the show where the two people seem to have anything in common. They don’t see this at first, of course, because they are too absorbed in the fact that they hate each other. For Dan, he has a preconceived notion that Blair Waldorf embodies everything he doesn’t like about the Upper East Side. He doesn’t admit this, but it also seems like he dislikes Blair because her friendship with Serena is a detectable threat to his long-term, pining goal of swooning her. When they finally do start to bond over films, books, and shared interests in art, they both keep the connection completely secret from everyone. This secrecy, though spurred by a desire to save face among their respective friend groups, ends up giving them a cloak of protection against the gossip machine. When Blair returns to her long-term distraction (Chuck Bass), neither of them suffer very long-term heartache, so, as far as doom goes, they both get off pretty easy.
12. Raina Thorpe & Chuck Bass
Largely quarantined to Season 4, Raina and Chuck’s relationship begins as FWB and continues into something much more genuine and vulnerable. Raina, outspoken and the daughter of one of the Bass family’s main business competitors, makes clear to Chuck that she doesn’t suffer fools. Unfortunately for Chuck, this includes him. When Raina overhears him in the middle of a bitter argument with Lily, his adoptive mother who presents as a kind woman only out to support him, she draws a line. The biggest tragedy to come from this ill-fated romance is that we lose Raina Thorpe, one of the show’s most fierce female characters, forever. Raina Thorpe deserved more airtime, especially considering there was so much to unpack about her life, not the least of which being that she had to turn her dad in for the accidental murder of her mother.
11. Jenny Humphrey & Nate Archibald
This relationship can only be so doomed, considering it doesn’t ever really get off the ground — something that upsets Jenny but is ultimately in her best interest. Nate acts as a kind of mentor to her, since he is a few years older, and they end up kissing once in Season 2. The rest kind of fizzles into an unrequited crush, with Jenny continuing to pine for a while before moving on with very little damage. One of the weirdest dynamics to emerge out of this almost nonexistent romance is the rivalry between Dan Humphrey and Nate. They already had some bad blood because they were in a not-so-subtle competition over Serena for several seasons, one that went into periods of passivity but never actually absolved. When it comes to blows between the two guys over Jenny Humphrey, it definitely seems like Dan is taking out other, unexpressed aggressions toward Nate.
10. Eric van der Woodsen & Jonathan Whitney
These two really, really did not have to be such a disaster. Jonathan seemed to have endless patience for Eric as he sorted out who he was, and went through several especially moody phases. Jonathan deserved better from Eric, who continually gets caught up in the cat-and-mouse drama of the Upper East Side and ends up morphing into the type of person that the two had previously been united against. In Season 4, when Jonathan realizes that Eric is not necessarily slipping into these bad habits but maybe that they are characteristic of him as a person, he finalizes the breakup for the last time. His disappearance highlights how little the show let him develop as a full character separate from this dysfunctional relationship, which is disappointing since these two were the only queer couple featured on Gossip Girl.
9. Blair Waldorf & Chuck Bass
Okay, it might not seem like this pairing belongs anywhere on this list; after all, they are one of the rare couples that stays together—as much as breaking up and getting back together one million times before getting married can be considered “staying together.” They’ve been through it all, literally. It can be hard to remember everything that Chuck put Blair through (selling her for a hotel, lying at every turn about basically everything, devising elaborate plans to tarnish her reputation, going into hiding in Paris to avoid ever seeing her again, etc.). As much as they seem to make each other happy in a strange, twisted way that only they can, their relationship is built on the backs of a lot of casualties, from those they led on while trying to make the other jealous to deeper, more substantial relationships that were never going to work out while the other still lived and breathed. Forging a bond that was more compulsion than love, the two do come to a kind of mutual understanding, but their complicated history cannot be completely erased.
8. Blair Waldorf & Nate Archibald
Speaking of the casualties of the Blair and Chuck fiasco… Nate, while objectively one of the least likable characters on the show, definitely got the short end of the stick here. The series begins after Nate, the long-time partner and established marital prospect of Blair, cheats on her with her best friend Serena. While Serena leaves town shortly after the incident, Nate stays behind and deals with the fallout. As the show follows him from partner to partner, and mistake to mistake, there’s something utterly helpless about all of his interactions that reads as relatively forgivable. He is much simpler than either Blair or Chuck, and it’s easy to see how he gets used like an unwanted chess piece between them.
7. Vanessa Abrams & Dan Humphrey
By this point, it’s probably become clear that Dan and Serena are not going to make this list. That’s not because they weren’t cursed on their path to marriage, necessarily, but more so that their many relationship woes were simply not very interesting. Dan and Vanessa, on the other hand, present a kind of tragedy. Best friends since they were kids, the two struggled to walk the tightrope between platonic intimacy and romance, and ultimately Dan’s obsession with Serena, as well as his crossing over into the superficial Upper East Side crowd that they both used to despise makes him unpalatable. What gives this disastrous romance its dramatic flair is that by the end, the two are practically arch-enemies.
6. Serena van der Woodsen & Colin Forrester
This relationship was destined for drama from the moment that their “meet cute” was Colin running into her several mornings in a row while he stole her cabs and sent them away with various women that he’d presumably slept with and needed to get rid of. Rough foot to get off on, and made rougher when he is appointed a guest professor for a class she’s taking at Columbia. There are some weirdly tense office hours, but luckily Serena sees him for what he is and dumps him before anything really happens. He’s got billions of dollars and what Serena feels is an intoxicating grin, but pretty much everything beyond this facade falls flat.
5. Serena van der Woodsen & Ben Donovan
As underwhelming as Colin was, as far as student-teacher relationships go, Ben is definitely… worse. In addition to being doomed, this one is just downright confusing, embedded in all of the semi-incestuous, telenovela-style coincidences that this show thrives on. Ben is Colin’s cousin, and he also used to be Serena’s teacher. But in high school. Nothing really happens when she’s a minor, but there is an unfortunate situation with a broken down car and the crossing of state lines that lands Ben in prison, with a vendetta that leads him to want to plot for her destruction. While this scheme seems like the main tenet of his character, he quickly gives it up when she still wants to date after he’s released. What may have started as a genuine connection ends up indistinguishable from the double-crossing, blackmail, and rumor mill that surrounds it.
4. Georgina Sparks & Dan Humphrey
It’s really hard to know how to categorize this relationship. It starts as a fling that neither of them appears very invested in, but since it’s Georgina, something weird definitely has to happen. And it does. After being away for a while, she shows up and informs Dan that she is pregnant with his child. Dan gets very responsible, letting her move into his loft and eventually signing the birth certificate for the child, Milo Humphrey. Of course, the child is not really Dan’s, which is par for the course for Georgina’s pathological lying. For a while there, Dan and Georgina seemed like a couple thrown together by necessity into learning how to raise a child together. It’s fair to say that the most luckless party of all is Milo, the little boy who will now be raised by Georgina.
3. Blair Waldorf & Louis Grimaldi
Oh, Louis. The meet-cute between Louis and Blair is straight out of a storybook. He approaches her at an art museum in Paris, where she is absorbed in looking at a painting. Louis takes dating Blair extremely seriously, and they actually do get married, despite his family’s persistent concerns that Blair is too common and won’t understand the intricacies of royal life. This is an intriguing development because the Waldorf family, wealthy as they are in the States, is almost indistinguishable from a kind of corporate royalty, so it takes a specific type of snobbery to consider Blair below someone’s paygrade. As far as their more intimate struggles, what’s most troubling about this relationship is that even though everything is completely perfect on paper, there is absolutely no way that they will work out, making them, in the truest sense of the word, doomed. What’s worse is that as soon as the marriage ceremony is finalized, Louis turns into an entirely different person, one perfectly content to trap Blair, leading her on an epic journey to attain a divorce that seems, on the face of it, like a legal impossibility.
2. Eva Coupeau & Chuck Bass
As far as fallout from the ongoing tug-of-war between Blair and Chuck, there is really no more depressing storyline than “Cheva.” In the episode “Last Tango, Then Paris,” Chuck gets shot in a dramatic and disorienting sequence of events. Luckily, Eva stumbles upon him and nurses him back to health. When he comes to, Chuck assumes a false name and attempts to build a quiet life completely disconnected from his troubles in the States. Eva is exceptionally lovely to Chuck, and only ever wants to be a supportive partner. When circumstances beyond their control bring Chuck back to New York, she struggles with self-esteem issues as she attempts to fit into his extravagant life. When the whole thing comes crashing down, Eva is heartbroken as she accepts that maybe the person she believed Chuck was really didn’t exist, under any name.
1. Ivy Dickens & Rufus Humphrey
The fact that this romance takes the number one slot may be a surprise, because it truly only lasted a split second in the Gossip Girl timeline. However, it would be completely irresponsible to let Rufus off the hook for this one. Ivy Dickens, hired by Carol Rhodes to pretend to be her daughter and infiltrate the Rhodes/van der Woodsen family in order to access her trust fund, makes a lot of understandable terrible decisions. She gets seduced by the extravagantly wealthy lifestyle, backstabs some friends, etc. The unforgivable choice was hooking up with Rufus Humphrey, especially since this is after going on a date with his son, Dan. It was a short-lived but extra-messy relationship that encapsulates all the deceit, tangled affairs, and high-society scheming that the series was known for. For so, so many reasons this will always be Gossip Girl’s most cursed romance.
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