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.

Spotted: Gossip Girl fans preparing to have some serious thoughts and feelings about what they're about to read.

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? 

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

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

Like a Hallmark Christmas movie gone horribly wrong.

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

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

This just felt so wrong. So, so wrong.

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

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

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. 

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

Snooze City, population: everyone.

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

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

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

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

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

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

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

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?)

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. 

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, in the end, Lonely Boy landed the Golden Girl…even though he tried to destroy her life through an anonymous blog for six years.

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. 

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

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…

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?

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. 

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Gossip Girl is available to stream on Netflix.

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