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10 Couples That Hurt Gossip Girl (And 10 That Saved It)

10 Couples That Hurt Gossip Girl (And 10 That Saved It)
29 Jun
8:28

Like most teen dramas, Gossip Girl had more than its fair share of couples. Considering the series followed a group of friends from high school to post-college careers, romance was inevitable. For a series on the CW, relationship drama is also a sure thing for most, if not all, couples.

With some couples, it was a relief when the two characters got together. With others in the series based on the books by Cecily von Ziegesar, it was not. Instead, in some cases, relationships hurt the show drastically.

In Gossip Girl‘s case, sometimes a couple is good at the beginning. You root for the characters to get together and sit through the inevitable conflict, even if it’s clearly unnecessary.You watch the couple breakup and find new love interests. Yet, you still want to see a reunion – at least until something happens that makes a reconciliation seemingly impossible.

For example, a big series finale reveal should have led to everyone hating a certain character, not a wedding. Fortunately, not all the series’ couples were awful. Some were a downright delight, maybe they were a fan favorite couple, simply better than the others or they brought a new dynamic to the show. With at least one pairing, it was a relief that the series took that step from friends to more for a little while.

In at least one case, having two characters get (and stay) together was the right move. It meant the end of unnecessary drama and the will-they-won’t-they aspect of their relationship.

Here are the 10 Couples That Hurt Gossip Girl (And 10 That Saved It).

20 Hurt: Nate and Vanessa


Question? Did anyone think Nate and Vanessa would end up together? The answer is probably no.

That’s why their relationship felt like something Gossip Girl had to get out of the way. In the first two seasons, they got together, broke up and then got back together. They also reconnected on their backpacking trip between seasons 2 and 3, but that was one night.

Nate and Vanessa’s had an on-again-off-again relationship. There was drama that surrounded their relationship, but there were indications that it wasn’t going to last. 

However, after that, the series clearly had to move on and explore other relationships for each character. It never felt like they had to put them back together. It wasn’t even really necessary for them to be together in the first place, other than to give Vanessa another connection in that world.

19 Saved: Eleanor and Cyrus


If only more Gossip Girl couples were like Eleanor and Cyrus, the series wouldn’t have been overrun with drama. Sure, they hit a bump in the beginning, when Blair tried to break them up, but that was it.

They benefited from not being one of the main couples because they could just be together and happy.

Cyrus didn’t just become Eleanor’s husband once they got married, he became a member of the family and helped Blair and Dorota over the years.

The couple moving to Paris didn’t stop him from buying Dorota and Vanya an apartment or helping Blair with her future (at the time) mother-in-law. He even officiated Blair and Chuck’s wedding.

It’s just too bad there couldn’t have been more of a focus on Eleanor and Cyrus. They were easily one of the show’s best couples.

18 Hurt: Nate and Blair


Nate and Blair were together before the show began, but he cheated on her with Serena. That provided a reason to root for them to be together and break up. On the one hand, they were childhood sweethearts.

However, he cheated on her with her best friend.

It’s hard to want a couple to be together after that and he (briefly) ruined a friendship. It was obvious Nate and Blair never would (or should) have stayed together from the beginning.

Their relationship seemed to exist to be the source of conflict in season 1 for Blair and Serena’s friendship. After that, there was no reason for it to continue.

The only good thing to come of it was them realizing in season 2 they were truly over.

17 Saved: Dan and Vanessa


Dan and Vanessa’s relationship was one that needed to be explored at some point on-screen. Was it one that should have lasted? Probably not. Was it one that could have lasted? Again, no. It was clear from the very start that Serena and Dan would end up together.

If the Gossip Girl reveal didn’t change that, nothing could.

Dan and Vanessa’s relationship may not have lasted, but they were two outsiders that got caught up in the drama of the Upper East Side.

However, Dan and Vanessa deserved better as a couple than they got. She was the one who got his story published in The New Yorker (as unbelievable as that was). They just ended up getting caught in the drama that was the Upper East Side and Gossip Girl.

Maybe they would have had a chance if their romantic connection didn’t have a scandalous beginning, thanks to Olivia.

16 Hurt: Chuck and Jenny


On the one hand, leaving the city was best for Jenny. That was something that Dan and Rufus agreed on when Gossip Girl’s identity was revealed in the series finale. A GG blast made that possible. However, the events leading up to that GG blast didn’t need to happen.

In the pilot, Chuck tried to take things too far with Jenny on a rooftop. Dan and Serena intervened and saved her. Two years later, Jenny had her first adult experience with Chuck, something that never should have happened.

Why Gossip Girl thought it was okay to have Jenny be with Chuck after what he did was a headscratcher. It was the wrong move and one of the worst things to ever happen in the series.

15 Saved: Serena and Nate


Yes, Serena and Nate may have first gotten together behind her best friend’s back. Their hookup was the moment that started everything, really.

Who knows what would have been different, if not for that? Anyone who likes anything that happened on Gossip Girl has them to thank.

It took until season 3 for the two to give a relationship a try. If Dan didn’t exist, it’s possible that they could have worked and ended up together. There would have been no reason for Serena and Dan to drift back together.

In the end, they sadly didn’t have enough drama to last, which says something given their history. That’s also why it would’ve been preferable to see them end up together, rather than Dan and Serena.

14 Hurt: Dan and Olivia


Remember when Hilary Duff was on Gossip Girl as an actress and Vanessa’s roommate at NYU? Remember when Dan wanted to be with someone normal? Somehow, the two ended up dating briefly. There seemed to be one thing after another when it came to their relationship.

Vanessa briefly interfered with their relationship over a toast at a dinner. Olivia lied about dating a co-star and she told an embarrassing story about him to Jimmy Fallon.

Olivia and Dan’s relationship may have been a short, but it was packed with drama.

He tried to keep her from filming a movie with a list of things college students needed to experience. They, along with Vanessa, did everything on the list, including some experimentation. It inevitably led to some jealousy.

Olivia ended up leaving to film a movie and was never seen again. So, what was the point of their relationship?

13 Saved: Dorota and Vanya


In the earlier seasons, Dorota was only really seen as the Waldorf’s maid but changed as the series progressed. She was also a fan favorite character (and a popular guess for Gossip Girl’s identity). There were even Chasing Dorota webisodes.

Her relationship with Vanya, a doorman in Lily’s apartment building, was never really a main focus of the series. However, it benefited from that because they could just be that sweet, romantic couple on the fringe of the other relationships’ problems.

His proposal is reason enough to love their relationship. “From the first moment I saw you, I knew you were [a] princess,” he told her. “And every day, you make me feel like [a] king.”

12 Hurt: Rufus and Ivy


Only on Gossip Girl could someone pretend to be someone else and then stick around. Not only did Ivy stay after everyone found out she wasn’t Charlie Rhodes, but she even got some money. That wasn’t the worst of it.

In fact, the worst of it wasn’t even the mess that was her and William’s relationship. No, that honor belongs to her and Rufus’ brief romance. It was completely unnecessary since it wasn’t like it was the final straw that kept Rufus and Lily apart.

By that point, that relationship had run its course. Instead, it seemed like the only point of Rufus and Ivy’s relationship was so Dan could walk in on them. No one needed to see that.

11 Saved: Serena and Carter


Serena and Carter would never have lasted, even if Dan wasn’t her endgame. The show would have had her end up with Nate or probably any of her other boyfriends before Carter. However, it wouldn’t have been the worst thing to have Blake Lively and Sebastian Stan’s characters together longer.

Carter really tried to show Serena that he changed and tried to redeem himself. It would have bee interesting to see how their relationship would have played if he didn’t lie about knowing where her father.

He started out as someone she would not be with and he had his problems. However, when they were together, he showed he’d changed (despite others conspiring to try to prove otherwise).

He was at his best and wanted to take responsibility for his past actions when he was with her. Lying about knowing where her father was wasn’t the right move, but it’s still better than being Gossip Girl.

10 Hurt: Nate and Jenny


If ever a relationship never should have progressed beyond a one-sided crush, it’s this one. It all started when Nate mistook her for Serena because of a mask at a ball. After that, the two became friends and that was where their relationship should have stayed.

Instead, after he moved into the Humphreys’ loft in season 2, he and Jenny got closer and eventually briefly dated. Cue the drama. Vanessa took a letter he wrote meant for Jenny.

In return, Jenny planned to get revenge by giving Vanessa an unlined dress to wear at a ball. It was childish and probably never would have happened, if not for Nate and Jenny moving past her crush.

Oh, and let’s not forget why Jenny decided to go to Chuck. She tried and failed to get back together with Nate.

9 Saved: Rufus and Lily


Anyone else wondering why Rufus and Lily didn’t end up together? He would have been the better option for her than William.

She would have made more sense than Lisa Loeb. Sure, their children got married, but even if Rufus and Lily had gotten back together, they weren’t related.

Yes, Lily’s relationship with Bart got in the way of them being together more than once. Having them finally get together was the right move by Gossip Girl. Their secret love child briefly appearing,  then disappearing to never be seen or heard from again was not.

The drama that followed as Lily hid her cancer treatments and William tried to win her back wasn’t either. However, for the most part, they were good together and it’s just too bad that they couldn’t reconcile.

8 Hurt: Blair and Prince Louis


Blair and Prince Louis’ relationship was just one of the many roadblocks in the way of the show’s endgame. Blair and Chuck were clearly going to end up together. Having Blair be with a prince wasn’t going to change that. In fact, having her date Prince Louis wasn’t even a problem.

Blaire and Prince Louis’ had a sweet relationship, but you could tell Blaire wasn’t truly in-love with Louis.

Why this couple hurt the series is that they got married. Blair actually went through with the wedding, even after a Gossip Girl blast including her love for Chuck. At the very least, that video should have meant the end of that royal relationship.

The fact that it didn’t and all the drama that resulted from it (including Blair’s pregnancy and Louis paying Chuck’s therapist) made it a painful storyline.

7 Saved: Eric and Jonathan


There were few same-sex couples on Gossip Girl. In the first season, Eric came out and he dated Asher, Jonathan, and Eliot over the course of the show. Even though Eric wasn’t as involved in the drama as the other main characters, his relationships weren’t conflict-free.

In the second and third seasons, Eric dated Jonathan but they broke up after Jonathan cheated on him. After Eric began working with Blair to embarrass Jenny, Jonathan broke up with him because he’d changed.

Despite that, it was good to see Eric have a storyline. It helps that this relationship didn’t have a negative effect on other characters as well.

6 Hurt: Dan and Georgina


This one is easy. Georgina pretended to be someone else when she first met Dan. That was back when Dan and Serena were together and Georgina was Serena’s frenemy. However, there’s one big reason why Dan and Georgina as a couple hurt the series: the baby.

Remember that time Dan thought he was going to be/was a father?

At the end of season 3, Georgina showed up at the Humphreys’ loft pregnant. Of course in a situation like that, it makes sense to get a paternity test. Dan did (or at least thought he did), but it turned out he wasn’t the father.

Georgina used him because he was the nicest person out of those she’d been within the right time frame.

5 Saved: Dan and Blair


Some people liked Dan and Blair together. Others did not. No matter how you felt, however, it was a pairing that had to be explored at some point. Once Gossip Girl had the two of them begin to become friends and bond over movies and art, it was inevitable.

If nothing had come from it, there would have always been that question of “what if?” That would’ve hurt the show.

Dan and Blaire’s relationship may not have been considered “end-game”, but it was happy to see the two characters bond over their love of movies and art. 

Their dynamic was entertaining enough that even though they weren’t at their best together, it didn’t ruin the series. It was never a relationship that was going to last because they were both really in love with other people.

Their endgames were obvious long before a romance was even a possibility.

4 Hurt: William and Lily


William and Lily were Serena and Eric’s parents, so they had a history. It wouldn’t have been entirely unbelievable for them to give a relationship another try. What was crazy was that they apparently ended up together, given the flashforward to Dan and Serena’s wedding.

That happened after, in an attempt to win his ex-wife’s heart, he used her health against her.

He faked her cancer after she’d gotten better because he’d fallen in love with her again. Rather than face any real consequences for that, everyone forgave him. Oh, and who could forget the fact that he had an affair with Lily’s sister?

William should have ended up alone, not with the woman he manipulated.

3 Saved: Jack and Georgina


Who would’ve thought that a bright spot in the mess of the series finale would be a new couple? The last episode of the show featured a time jump to Dan and Serena’s wedding.

At some point during the five years, Jack and Georgina apparently got together. Surprisingly, it wasn’t the worst thing to happen.

Really, of the new (or reunited) couples shown gathered for the wedding, they were easily the best. (Lily and William back together made no sense, nor did Rufus and Lisa Loeb dating.)

Neither Jack nor Georgina would ever be called a good person, even by Gossip Girl standards, but maybe they worked together. It’s too bad there wasn’t more of their relationship on the show.

2 Hurt: Dan and Serena


Lonely Boy and S. The fact that they got together isn’t the problem. In the earlier seasons, it wasn’t hard to root for them. However, as the series went on, it became increasingly difficult to do so. That was not just because they had other relationships, other love interests are the norm on teen dramas.

Even if Dan and Serena were meant to be together, they shouldn’t have got together after Dan revealed he was Gossip Girl.

Instead, it all built up to the finale, in which Dan revealed he was Gossip Girl. While everyone, especially Serena, should have been mad at Dan, they all got over it in a few moments.

Serena even called what he did a “love letter” and married him. She married the person who posted horrible things about her online. Dan and Serena could have been a couple that saved the series. Instead, because he was Gossip Girl, they never should have ended up together.

1 Saved: Chuck and Blair


Chuck and Blair’s on-again-off-again relationship had its ups and its downs. It was never the healthiest of the relationships on Gossip Girl. However, it was one that fans could root for because it was inevitable that the series would end with them together.

In fact, the series probably would have benefited from the two of them being (and staying) together sooner. It was best when the drama and the will-they-won’t-they were out of the way.

Some of the most romantic moments of the show came from these two, whether it was Blair making sure Chuck knew she was all in or the two of them taking time to profess their love during a quick wedding.

Are there any other couples that you think saved or hurt Gossip Girl? Tell us in the comments!

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