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?