“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.
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.
￼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.￼21. 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!
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