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? The series' 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 for 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 the—OMFG—16th anniversary of the OG series' premiere. 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...