We Ranked All the Gossip Girl Couples and No. One May Surprise You

In honor of Penn Badgley's birthday, we're doing a romance rewind on the hit CW series' best and worst pairings.

By Tierney Bricker Nov 01, 2020 7:00 AMTags
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Good morning, Upper East Siders. Are you ready to celebrate Penn Badgley's 34th birthday by taking a stroll down 5th Ave memory lane? That's right, in honor of Lonely Boy's big day, we're revisiting the CW hit series' by ranking all of its pairings—the good, the bad and the oh-so-very pretty. 

Over the course of its six-season run, Gossip Girl worked its way through almost every pairing imaginable. Nate (Chace Crawford) dated just about every female that appeared on the show, while Serena (Blake Lively) also had her fair share of love interests. And c'mon, who can forget about Chuck (Ed Westwick) and Blair (Leighton Meester), with the pair going on to become one of TV's most beloved couples. 

But was that able to snag them the top spot in our ranking? Or was another pairing able to defeat "Chair" and claim victory? 

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. Nate and 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!)

17. 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. 

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, you never forget your 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, like, really 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 pretty much 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. A marriage counselor's dream session!

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 Friends' Ross and Rachel, The O.C.'s 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 guys, college, jealousy issues and what not, B and S did besties better than anyone. You know you loved them. XOXO. 

Gossip Girl is available to stream on Netflix.

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