You never forget your first Gossip Girl.

While the franchise may have been rebooted for HBO Max in 2021, let's be honest: the OG series, which premiered in 2007, is still the number one GG in our hearts. And a large part of its enduring success? It's many couples, with the characters switching partners faster than little kids jacked up on birthday cake play musical chairs. Serena (Blake Lively) romanced Dan (Penn Badgley) and Nate (Chace Crawford), both of whom also dated her BFF Blair (Leighton Meester). And she was in a relationship with Chuck (Ed Westwick), who secretly was with Vanessa (Jessica Szohr), who...okay, you get the point and honestly, we're exhausted. Alas, not all of the CW series' pairings were created equally. While some 'ships proved to be epic, others didn't exactly inspire fans to say those three words made up of eight letters. Because or every "Chair" (Chuck and Blair, duh), there's whichever random blonde dude Serena was interested in. 

The varying success of chemistry is why we decided to rank 25 of Gossip Girl's couples in honor of our Queen B Leighton Meester's 36th birthday on April 9. Because haven't you heard? We're the crazy b--ch around here. 

So, which pair  topped our list of the Upper East Side' best and worst pairings? That's a secret we're dying to tell...

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!)

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

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. 

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, you never forget your 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, like, really 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, 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!

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 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?

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.