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 HBIC Leighton's 38th birthday 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...
25. Chuck and Jenny
24. Blair and Prince Louis
23. Bart and Lily
22. Rufus and Ivy
21. Nate and Jenny
20. Dan and Georgina
19. Dan and Olivia
18. Nate and Ivy/Lola/Juliet/Rayna
17. Serena and Tripp
16. Nate and Vanessa
15. Dan and Vanessa
14. Blair and Lord Marcus
13. Rufus and Lisa Loeb
12. Serena and Ben/Aaron/Steve/Colin
11. Jack and Georgina
10. Nate and Blair
9. Dorota and Vanya
8. Nate and Serena
7. Eric and Jonathan
6. Dan and Serena
5. Rufus and Lily
4. Cyrus and Eleanor
3. Dan and Blair
2. Chuck and Blair
(Originally published Sunday, April 9, 2023, at 6 a.m. PT)
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