Gossip Girl: Ranking The Relationships I Couldn't Get Enough Of, For Better Or Worse

Chuck and Blair in Gossip Girl.
(Image credit: The CW)

I did it. I finally did it. I watched Gossip Girl.

No, not the new HBO Max abomination that came out that we will not discuss here, or ever again, because it was cancelled, but the original CW show. It was incredibly popular during its time on the air, and that's only continued with its fans watching on streaming platforms now. As an adult, I decided to give the entire series a shot and I must say – wow, lots of fun stuff in this show, and things that drove me absolutely nuts – but that’s sort of par for the course with CW shows.

However, there was one thing in Gossip Girl in particular that I found myself drawn to, and that, my friends, was the relationships. The romances in this show truly made my life and I absolutely loved watching them. All these Gossip Girl relationships were honestly some of the best parts of the show, and today, I’m going to get into the relationships that I just couldn’t get enough of – for better or for worse. 

Carter and Serena on Gossip Girl.

(Image credit: The CW)

8. Serena And Her Non-Dan/Nate Love Interests

We’ll get into Dan and Nate later on, but first off, I just have to put this at number eight – Serena and literally any of her other love interests that weren’t those two. I just loved every story with them. 

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Whether it was because of Blake Lively’s incredible acting or just how messy they were, I couldn’t get enough. They would never last too long, sometimes only a few episodes, maybe even just one, but they always left a lasting impression. 

I'm talking about the likes of Sebastian Stan’s character, Carter Baizen, or Colin Forrestor (played by Sam Page) who literally quit his professor job at Columbia to be with her. Talk about messy. 

Dan and Blair on Gossip Girl.

(Image credit: The CW)

7. Dan And Blair

God, this couple was the epitome of hate-watching. I despised this couple so much, but at the same time, it was like a car crash. I couldn’t look away. 

This was not my typical, favorite enemies to lovers story, because it really didn’t feel genuine. Their relationship felt like it really happened out of nowhere and because of that, it was quite hard for me to swallow as a viewer. But that also meant that I was fully invested in this relationship ending because literally Dan and Blair are two of the most incompatible people ever. 

I always love Penn Badgley and Leighton Meester, but them together just didn’t do it for me. However, it was fun to watch it go down. 

Rufus and Lily in Gossip Girl.

(Image credit: The CW)

6. Rufus And Lily

I’ll be honest, a lot of people seem to like Lily and Rufus, but to me, they feel just sort of…meh. 

I’m not sure what it is. I definitely enjoyed watching them in the show, hence why they’re number six, but I feel like their relationship could have been a little spicier and had a lot more fun moments rather than how vanilla it actually was. The only real interesting storyline they had was their secret son they never told anyone about. 

That was sort of dropped, though, and never spoken about again, so I can’t put them higher than six. At least they weren’t that toxic. 

Cyrus and Eleanor in Gossip Girl.

(Image credit: The CW)

5. Cyrus And Eleanor

Oh my god, I loved Cyrus and Eleanor so much. They were honestly the sweetest couple out of everyone on this list. 

It was a relationship that really no one was expecting to happen, but Blair’s mother, Eleanor, marrying Cyrus (played by Wallace Shawn) was one of the best decisions the show ever made. Cyrus was such a kindhearted, warm man who genuinely wanted only the best for Eleanor and Blair, and you could tell by how close Blair ended up being to Cyrus, and how much Eleanor and Cyrus were in love. 

If they had expanded on their relationship more in the show, they would have been higher, but I must say they are my personal favorite without any drama. 

Blair and Lord Marcus in Gossip Girl.

(Image credit: The CW)

4. Blair And Lord Marcus

I mean, we all knew Blair would be around someone with royal ties at some point during the series, and Lord Marcus felt like he would be a perfect match for her. He was kind, rich, and had connections that could give her everything she ever wanted. They had a good thing going. 

And then we found out he was having sex with his step-mother and that all went to garbage. 

It’s that singular moment that bumps this couple all the way up. That sort of storyline is so messy and yet, I just can’t look away. It was something that made my head do a full 180, and I needed to see how this relationship ended. Truly one of the craziest moments of the show. 

Nate and Serena in Gossip Girl.

(Image credit: The CW)

3. Nate And Serena

To be honest, I actually really liked the dynamic between Nate and Serena, even though I don’t really think their relationship was super healthy. Obviously, you can’t help but love Chace Crawford (who is killing it now in The Boys on Amazon Prime) as Nate and his interactions with Serena, but I have a feeling that if there wasn’t the history with Blair, these two would have ended up together in the end. 

They had their own story, their own vibe, and came from the same world of the Upper East Side. They could have been the golden standard for couples, but alas, it all fell apart. 

Dan and Serena on Gossip Girl.

(Image credit: The CW)

2. Serena And Dan 

Look, yes, I know Dan is Gossip Girl, and he spent a ridiculous amount of time trying to ruin Serena and everyone else’s life, but that’s what makes this partnership spicy. 

Yes, Dan is a problematic man and honestly needs to go to therapy for how often he focused on other people’s problems, but let’s be real here – Dan and Serena in Season 1 was great, and even later on, any time they were together, they had some excellent chemistry. A lot of fans found it hard to believe that they married at the end of the series, but I can see it. 

This may sound a tad problematic, but Serena likes someone who can keep her on her toes and Dan sure did that with his blog. Don’t think they would have made it past a few years of marraige, though. 

Chuck and Blair in Gossip Girl.

(Image credit: The CW)

1. Blair And Chuck 

I mean, was there ever any doubt? 

Chuck is literally the worst, and I will stand by that. And Blair honestly wasn’t that much better. It took a crazy amount of character development for me to like either of these two and think that their relationship was meant to be, but even by the messy end, I actually thought that out of everyone, they deserved each other. 

Admittedly, they both did change a lot by the end of the series, but wow, this relationship was truly something I could not get enough of, through the toxic moments and everything else. 

Gossip Girl was a marvel of its time and I’m happy that it’s over with now and I never need to return to the world of the Upper East Siders – or any of these relationships. I’ll just check this off of my watch-list and look for something a little less toxic in my favorite teen dramas

Stream Gossip Girl on HBO Max.

Alexandra Ramos
Content Producer

A self-proclaimed nerd and lover of Game of Thrones/A Song of Ice and Fire, Alexandra Ramos is a Content Producer at CinemaBlend. She first started off working in December 2020 as a Freelance Writer after graduating from the Pennsylvania State University with a degree in Journalism and a minor in English. She primarily works in features for movies, TV, and sometimes video games. (Please don't debate her on The Last of Us 2, it was amazing!) She is also the main person who runs both our daily newsletter, The CinemaBlend Daily, and our ReelBlend newsletter.