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!