Relive Most Memorable 'Gossip Girl' Hookups (PHOTOS)

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In honor of Gossip Girl’s season five premiere tonight, Sept. 26, we are counting down the show’s best hookups. Whether steamy, crowd-pleasing, or unexpected, we can always count on Gossip Girl to provide us with the most complicated love triangles, forbidden loves, and even threesomes! Click the pics and get a more detailed look into the hookups below! 

10. Nate and Serena - While Nate (Chace Crawford) and Serena (Blake Lively) didn't last too long into the series, this was a significant hookup that showed how Serena and Blair (Leighton Meester) are the ultimate frenemies. It tore the friendship apart but of course, the drama of the Upper East Side brought them back together again.

9. Blair and Nate - Eat your heart out Chuck Bass (Ed Westwick)! After a messy breakup, Nate and Blair rekindled their flame with a seriously naughty make out sesh. While it was fun at the time and the relationship was on-again off-again, the two were definitely not meant to be.

8. Jenny and Nate - While it lasted only a short time, Jenny (Taylor Momsen) and Nate's relationship was definitely a memorable one thanks to the age difference and the fact that Nate was supposed to be Dan's friend. Awkward! 

7. Vanessa and Dan – Best friends turned friends with benefits. We all know that in real life, this never works, but it did not surprise us when it happened with Vanessa (Jessica Szohr) and Dan (Penn Badgley). After this romantic relationship, it was hard for them to ever get back on track.

6. Nate and Catherine the Duchess – Remember this one? Blair was dating Marcus, a lord. Meanwhile Marcus’ mother, a duchess, was getting naughty with Nate in the library! Talk about complicated!

5. Dan and Georgina - We all sat at home watching, screaming at our televisions, "DON'T DO IT!" We saw Georgina (Michelle Trachtenberg) was crazy but Dan was blinded by her seductive ways. This hookup even led to Georgina announcing that her baby was his - which thankfully was just a lie.

4. Dan and Blair – A fairly new romance, that seems to have already passed. It all started with their internship at W Magazine and ended when they finally kissed and Blair “didn’t feel anything”. Oh well…more chance for Blair to get back with Chuck and Dan to get back with Serena!? Positive thinking.

3. Dan, Vanessa, and Olivia - We all know that college brings about new life experiences but we doubt Dan Humphrey had any idea he would find himself in the middle of a steamy threesome. Dan's face is priceless when he finds himself watching Vanessa Abrams and guest star Olivia (Hilary Duff) making out right in from of him! Definitely a Gossip Girl hookup to remember.

2. Dan and Serena - Another crowd favorite, a beautiful couple who end up being step-siblings! Coming from opposite ends of Manhattan, Dan and Serena became fascinated with each other. Things fell apart when their parents got married, but we have never given up hope that the two will get back together. While it seems far-fetched at this point, the two are currently single. We can keep wishing!

1. Chuck and Blair - Ever since Chuck (Ed Westwick) opened up and said those three little words Blair needed to hear, this couple is arguably one of the favorites on television. With their scheming and conniving, Chuck and Blair always have always proven to be meant for each other, even if she is currently engaged to a prince.

There we have it. The upcoming season is sure to bring out even more memorable hookups so make sure to tune in Monday at 8 p.m. to The CW to see what will happen next!



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  • Pankaj

    I saw it opening night, front row, in a paekcd theater full of people who somehow had no idea what they were about to see. Like most movie freaks, I had already heard, read, and watched as much as possible in the weeks beforehand, so I was obviously not watching it thinking, "Did this really happen?" (as it is, I can't believe that myth lasted any longer than opening day but it's worth noting that this was prior to the days when people could so easily look up information online). So although I knew it was fake, much of it still freaked me out, and that night I coincidentally was staying the night at a friend's house in a dark, cement-walled, windowless basement. I slept not a wink.

  • ann

    Looks photoshopped....

  • Emilija Vanagaitė
    Emilija Vanagaitė

    That wasn't Dan.It is fake.It was Nate,duh...

  • tabachu

    i'm so inlove w/ their chemistry.. ^@^

  • Christiana

    The one with Brair and Dan is fake. She was suppost to kiss Nate in that scene. And guys Chack and Blair have the the kisses!!

  • Bonnie

    I love Chuck and Blair and want them back ASAP!

  • LF

    Chuck and Blair are number one because they're the only awesome couple on this show. And LOL! that that's a fake pic of DB. Ha!

  • Caitlin

    Chuck and Blair. Blair and Chuck. Of course they are number one. No other couple compares. :)

  • Lilly

    LOL! Dan and Blair has no pictures together, aww they have one yeah! it was one which they kissed and made Blair want to vomit. Chuck and Blair are the hottest couple around.. Watching GG just for them.

  • Emily

    Creepy manipulation picture aside, I loved Chuck and Blair, and DS, but where's NS? That's got to be better than D with Georgina or Olivia! Seriously, lol.

  • Olivia

    Love the Chuck and Blair kiss (that Dan/Serena one is hot as well). The Dan and Blair on you posted didn't actually happen, since that's a photoshop... LMAO.

  • harumscarum

    CHAIR and derena ftw!

  • harumscarum

    no i'm pretty sure chair is in the number 1 spot. and for good reason, i might add ;)

  • Lisa

    Chuck and Blair are by far the beat thing about Gossip Girl so yes they ate the best, hottest and sexiest hook up/relationship.

  • dr

    lol they look terrible...not "organic" at all...

  • allym

    Yum!...LOL! :P

  • Olga Elenna Estay Diaz
  • Olga Elenna Estay Diaz
    Olga Elenna Estay Diaz

    haha cue kiss!

  • Tyler

    What about Chuck and Jenny???

  • Katy

    haha, he is so cute :D

  • Blair

    What a stupid post!? Why would you even begin to tell us who's best. We should decide who we like. Boo, I prefer Dan Humphrey and Blair Waldorf and Nate and Serena.

  • Charlie

    DAIRRRRRR is number 1!!!

  • Urszula

    Those were some amazing kisses. Coincidently, my boyfriend and I had the most sensual kiss last night which made my head spin and my heart miss a beat. My boyfriend is an amazing kisser and he knows exactly what to do to turn me on in all the right ways.