We Ranked Gossip Girl's Couples, Prepare to Have Thoughts and Feelings

In honor of the HBO Max revival's debut, we're doing a romance rewind on Gossip Girl' best and worst pairings.

By Tierney Bricker Jul 11, 2021 1:00 PMTags
Watch: "Gossip Girl" Is Back: Live From E! Rewind

You know you love them, XOXO.

You never forget your first time, especially if you were and are a Gossip Girl fan. The iconic series' revival premiered on HBO Max this week, introducing viewers to the next generation of Manhattan's elite. While they're just as dramatic and gorgeous as their predecessors, time (and Twitter) will tell if their onscreen romantic entanglements can hold up to the OG's bevy of beloved couples. Remember the days when "Chair" just meant something you sit on? 

As we wait to see how GG's new pairings play out, we're taking a walk down Fifth Avenue memory lane to reminisce on the many relationships the CW series offered up over the years, ranking them from worst to best. Because even after all this time, we still have a lot of thoughts, feelings, concerns and think pieces in us about the romantic musical chairs that went down on the Upper East side back in the day. Seriously, did any pairings not hook up during its six-season run?

Gossip Girl Cast: Where Are They Now?

Find out which couple topped our list of the UES' best and worst pairings...


25. Chuck and Jenny

Nope. Gross. Need bleach for our brains, please and thank you. 

24. Blair and Prince Louis

Like a Hallmark Christmas movie gone horribly wrong.

23. Bart and Lily

Who knew two robots could fall in love? And make each other even more intolerable?

22. Rufus and Ivy

Shudders. Still not recovered from this. PTGGD is real, y'all.

21. Nate and Jenny

This just felt so wrong. So, so wrong.

20. Dan and Georgina

Remember when she convinced him they had a child together? HAHAHA.

19. Dan and Olivia

Never forget their threesome with Vanessa. (Before she ran off to continue being a movie star. Totally relatable!)

18. Serena and Tripp

We won't lie, we were into Serena hooking up with Nate's married politician cousin at first…before he left her at the scene of a car accident. And tried to pin it on her. BY MOVING HER UNCONSCIOUS BODY. Talk about taking ghosting to a whole new level. 

17. Nate with Ivy/Lola/Juliet/Rayna

Can anyone really distinguish any of these relationships? No? That's what we thought. (You can add Sage, Bree and Diane in here, too!)

16. Nate and Vanessa

Snooze City, population: everyone.

15. Dan and Vanessa

Of all Vanessa's relationships, this was the least awful. So that's technically a win ?

14. Blair and Lord Marcus

Total catch…until it was revealed he was banging his step-mother. Don't you hate it when that happens?

13. Rufus and Lisa Loeb

Still LOL-ing over these two ending up together. Sure, why not?!

12. Serena and Ben/Aaron/Steve/Colin

Like, can you even tell which guy is which? Exactly. 

11. Jack and Georgina

Hey, if any two people were tailor-made for each other, it's this gruesome twosome.

10. Nate and Blair

Ah, first love. These two were cute (if you forget the cheating and all), but not in an epic way. 

9. Dorota and Vanya

So cute, but so peripheral. A web series about their home-life probably would've been pretty funny. 

8. Nate and Serena

We'll always have that gorgeously lit steamy flashback bar romp, right? Still, they were a little bland, with their romance being much more central and meaningful in the book series. (But they were so, so pretty, right?)

7. Eric and Jonathan

A sidelined romance that didn't get enough screen-time, in our opinion! (Ditto Eric as a character, in general.) Still, they felt like a real couple. 

6. Dan and Serena

Serena. Married. Gossip Girl. WHAT?! Sigh…while they were kind of ruined by the end, season one Derena was kind of epic, right? And hey, Lonely Boy landed the Golden Girl...even though he tried to destroy her life through an anonymous blog for six years.

5. Rufus and Lily

We are still SO mad at the writers for screwing this one up. They had such a rich history and star-crossed—or crosstown, to be more precise—romance that was not paid its proper respect in the end. 

4. Cyrus and Eleanor

"Not enough" of these two! We aspire to have a marriage like theirs, TBH. 

3. Dan and Blair

Yes, we dared to "Dair." BYE HATERS. Seriously, these two, out of all the main characters, were the most well-suited for each other. In real-life, they would've been endgame. However...

2. Chuck and Blair

From that first show-changing hookup in the limo, "Chair" became one of TV's most iconic couples, right up there with Ross and Rachel, Seth and Summer, etc. Sure, they had their ups (Chuck finally saying "I love you") and downs (Chuck sold her for a hotel), but these two were made for each other. They were inevitable. 

So what couple could possibly beat "Chair" for the throne?

1. Blair and Serena

Boys may come and go, but friends are forever. And, despite the arguments over the years over guys, college, jealousy issues and what not, B and S did besties better than anyone. You know you loved them. XOXO. 

Gossip Girl is streaming on HBO Max.

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