#TBT: Gossip Girl’s 30 Couples Ranked From Best To Worst

Becca Van Sambeck
Becca is a recent Fordham grad, a former German beer hall girl, and a new Brooklyn resident who used to read the dictionary for fun as a kid. She has only gotten slightly less lame since then. She loves pugs, chicken fingers, reading and Game of Thrones.

“Gossip Girl,” the show of our generation, had it all: Glamorous parties, life-ruining secrets, amazing headbands, Blake Lively’s legs, a narrator that made “A” from Pretty Little Liars look like a kindly old grandma, and, of course, lots of romance.

In honor of Valentine’s Day, we’re counting down all the relationships on Gossip Girl, from best to worst.

1. Dan and Serena

Sure, Blair and Chuck were the couple that everyone obsessed over, but Dan and Serena were the couple that started and ended the series. Dan became Gossip Girl for Serena! There wouldn’t be a show without Dan’s obsession over Serena! If that’s not love, I don’t know what is.2. Blair and Chuck

This couple arguably made “Gossip Girl” popular. Girls everywhere swooned over the reformed bad boy and the whole “Three words. Eight letters. Say it and I’m yours” thing. It’s also true that watching Blair and Chuck play mind games with each other was basically the plot of every episode of “Gossip Girl.” They survived it all — a marriage to another person, a shooting in Thailand, a murderous rival tycoon, Chuck selling Blair in exchange for a hotel — but these crazy kids made it work in the end to the delight of every “Gossip Girl” fan.

3. Dan and Blair

Was there ever a more controversial love story than Blair and Dan? But c’mon, now that we know she ended up with Chuck, can’t we admit they were pretty cute together? They both thought they were the smartest people in the room. They loved all the same books and movies. They had a sweet and loyal friendship first that naturally blossomed into love. It’s a really good love story!

4. Serena and Nate

Nate and Serena were both Golden Retriever puppies personified — beautiful, rich and stupid that they made a magnificent couple.

5. Dan and Vanessa

Pretentious, wannabe artists who act like they’re so above their Upper East Sider friends while engaging in all the same petty, self-destructive behavior. And we saw that giant Williamsburg loft, Dan — let’s not act like you’re actually poor. These two were actually quite well-suited.

6. Blair and Nate

Blair and Nate had that sweet high school love that just couldn’t compete with their love for best friends. Still, they had their moments.

7. Dan and Georgina

Dan and Georgina were two people you couldn’t leave behind. Sure, she lied and said the baby was his when it wasn’t, and yes it was a little bizarre Dan would jump into a relationship with a girl who proven herself to be a crazy bitch out to destroy him and all his friends, but I don’t know. I sensed a spark.8. Serena and Gabriel

Serena showed us that she really was kind of stupid when she fell for this businessman’s Ponzi scheme. Buuuut, he was played by the extremely attractive Armie Hammer, so we do kind of get it.

9. Dan and Olivia

Remember when Dan dated a movie star, Olivia, played by real life movie star Hilary Duff? That was nice.

10. Serena and Carter

Carter was suppose to be kind of sleazy, but somehow he and Serena made just the loveliest couple.

11. Chuck and Eva

Eva actually seemed like a very nice French girl, so of course it couldn’t work.

12. Jenny and Damien

Damien is pretty cute and got Jenny into dealing drugs, and that was a pretty fun storyline. I approve!

13. Nate and Vanessa

Nate and Vanessa tried to have this whole “opposites attract” coupling, but it did kind of make sense that Vanessa would ditch her moral compass and standards for someone as sexy as Nate.

gossip girl nate archibald vanessa abrams nate and vanessa

14. Nate and Sage

This was fun just because Nate’s ex-girlfriend, Serena, is dating Sage’s dad at the same time. Serena could’ve been Nate’s mother-in-law. Imagine.


15. Vanessa and Scott

The couple that always gave me the most heat was Rufus and Vanessa, and since she never did end up with the only dad on the show, the closest we got was her relationship with his illegitimate son.

gossip girl vanessa abrams
16. Nate and Jenny

Nate rescued Jenny from bad situations like a million times, so it made sense that she was so head-over-heels for him. Why he was drawn to a random whiny freshman was a little more confusing.


17. Serena and Aaron

Serena proved once and for all she had a type when she started dating this douchebag artist in Season 2.

18. Serena and Steven

In season 6, everyone was worried Serena had vanished and went off the deep end, but she had just created a fake identity and was living with an older man, as one does.


19. Nate and Catherine

Nate loved his affairs with older wealthy women, but Catherine was more fun than Diana because at least her British accent sounded believable.

20. Dan and his Teacher, Mrs. Carr

Ugh, remember when Dan was a high school student sleeping with his teacher? Just because Dan looks like a 26-year-old doesn’t mean its not illegal or creepy in the world of the show.1121. Serena and Tripp

Oooof, Serena did little to help her reputation when she became a politician’s mistress, This would be a little bit more forgivable if Tripp had like, any charm at all.22. Blair and Marcus

Blair lived out her princess fantasies by dating a British lord, but he was sleeping with his stepmom the whole time so the whole low-level incest thing kinda takes away their heat.23. Nate and Juliet

AKA Nate continues his string of dating women who were out to get Serena.24. Nate and Raina

AKA Nate broke the bro-code :/25.Nate and Bree

I don’t know, Nate dated this redhead once, didn’t really seem like there was much to this storyline.

26. Serena and Colin

You probably don’t remember that Serena had a brief fling with a college professor, which says a lot about Serena — that sleeping with her college professor was just kind of whatever in her love life.27.Chuck and Raina

Points deducted because Raina was an accomplice to the whole “Bart’s murderous rival tries to take down Chuck” storyline and that was kind of stupid.28. Nate and Charlie

The less that is said about Charlie/Ivy, the better.29. Nate and Diana

Diana’s stupid accent was just painful, and even though she was an older woman she was spending all her time just fucking around with teenagers’ heads, which is kind of sad. Oh, and she owned a secret brothel? Nate could do better.30. Serena and Ben

OH, these two, NO. We find out Ben was Serena’s high school teacher who went to jail after being falsely accused of sleeping with her-but judging by the fact that he promptly started a relationship with her upon his release from prison, it’s safe to say that he really did want to sleep with a ninth grader, sooo ick.31. Blair and Louis

OH MY GOD WHY. THE FACT THAT WE HAD TO DEAL WITH PRINCE LOUIS AS A CHARACTER FOR SO LONG WAS A GODDAMN TRAGEDY. AND OF COURSE HE TURNED OUT TO BE EVIL, AND HE WAS SOMEHOW STILL SO BORING! NAME ONE PERSON WHO EVER LIKED LOUIS AND HIS LISP. NOBODY WAS ROOTING FOR HIM TO BEAT DAN OR CHUCK!

subscribe

SIGN ME UP