Top 10 Most Shocking Gossip Girl Moments

This story line is completely crazy from start to finish. For his entire life, Chuck believed that his mother died giving birth to him. As it turns out that was a lie by Bart Bass. While at Daddy Dearest’s grave, Chuck meets Elizabeth, and thus begins one of the most convoluted stories in Gossip Girl history. We practically got whiplash from all the back and forth, is she, or is she not the mother drama. So many lies! Another woman even claimed to be Chuck’s mother at one point for some duplicitous reason. But after years of searching, Chuck finally finds out the truth: Elizabeth Fisher is his birth mother.

They might have become GG's IT couple, but back in season one, this hazy hookup was a real shocker. Chuck was the bad boy player and Blair was the good girl who went out with his best friend. But during the short period of time that she and Nate were broken up, she and Chuck shared a few defining moments that made them see each other in a different light. You could definitely start to feel that things were starting to develop between them, but it all happened so suddenly. One minute they’re annoying each other, and the next, they are making out in Chuck’s limo. Mind blown.

Georgina's entire purpose on the show was to stir up trouble. As if this show needed any more bad behavior. After the way she played Dan so spectacularly when she first came back to New York, he must have been absolutely insane to hook up with her again. And yet, he fell victim to one of her most dubious schemes ever: she shows up on Dan’s doorstep and drops off a baby that’s apparently his. But what’s an even bigger twist than Georgina randomly showing up with Dan’s baby, is that no one found this at all sketchy and just believed her for quite some time.

Chuck and Blair have done some pretty terrible things to each other over this show’s six season run, but this has definitely got to be the worst. Chuck has an especially sordid relationship with his family, so why he ever trusts any of them is a mystery that may never be solved. When Jack Bass comes to town seeking revenge on Chuck, he hoodwinks Chuck out of his most prized possession at the time: his hotel. He tells Chuck that he will give it back if he offers up a night with Blair... and he makes the trade. Yeah, as if it is his to give. Chuck willingly sells Blair to his uncle for a hotel, and all of our jaws hit the floor.

Drama just seems to follow Chuck and Blair around like a shadow. When Blair decides to leave Louis and run away with Chuck, you could just feel it in the air that things were too good to be true and something bad was going to happen - but no one could have expected this. What makes this particularly interesting is that we experience the crash from Nate's point of view. He is in the vehicle behind Chuck and Blair, and though he has no idea what's going on, you can feel some kind of tension before the crash even happens. You hear the crash from Nate's car and see his shocked reaction. And we were all right there with him.

There have been quite a few unlikely pairings on this show, but this one beats them all. After pretty much ruining her relationships with all of her friends, Jenny goes to look for Nate for some comfort, but finds Chuck instead. He is also depressed because he thinks Blair bailed on him again. In a moment of desperation, they turn to each other and end up in bed together. The whole thing is extremely cringeworthy, especially because Jenny really needed a friend, and Chuck took advantage of the vulnerable situation. And because Jenny ends up losing her virginity to the same guy that previously tried to force himself on her. One of the most cringeworthy things to ever happen on the show. Were you screaming at your screen? Because we were.

The big mystery behind why Serena left New York had been looming over her friends for a year. It was the catalyst of season one. And when the big secret was finally revealed to everyone that Serena hooked up with Blair’s then-boyfriend, Nate, we all thought that was the end of that particular strain of drama, but we were wrong. Turns out, Serena had another big secret that she’d been keeping to herself. After starting to resort to her former self destructive self, her friends stage something of an intervention and she confesses that she was partly responsible for someone’s death. Off all the things that Serena could have possibly revealed, did anyone expect it to be that?

Okay, there is a lot to unpack here. Let’s start with Bart’s first death. Allegedly, Bart was in a fatal car accident while on his way home. They had a funeral and everything and Chuck was surprisingly destroyed. Then a few years later, Bart returns from the dead revealing that he faked his first death to escape some shady dealings he’d been involved in. But, come on, did any of us really believe that that car accident was the end of Bart Bass? Finally, after having Nate arrested, threatening Blair, and trying to kill his own son - man, this dude could throw a tantrum - Bart and Chuck end up in a huge fight to the death on the roof of one of his buildings... and Bart goes over the edge.

This comes completely out of nowhere. After his failed attempt to propose to Blair, Chuck travels to Prague to escape New York for a bit. Practically upon his arrival, Chuck is randomly confronted by a couple of muggers who try to steal not just his money, but also the engagement ring he planned to give Blair. When Chuck refuses to give up the ring, the muggers shoot him, leaving the season on a life or death cliffhanger. It’s even more shocking that, with the way this show works, the shooting didn’t turn out to be some kind of masterfully orchestrated evil plot against Chuck. The other shoe just never dropped.

Before we unveil our top pick, here are a few honorable mentions.

The Reveal of Lily & Rufus’ Son, Scott
“Rufus Getting Married”

Dan & Blair Kiss
“Empire of the Son”

It’s a Sham Marriage Between Blair & Louis
“G.G.”

No one could have suspected that Dan of all people would turn out to be the infamous Gossip Girl. This was a huge controversy among fans of the show as many believe it was impossible for Dan to be GG. Surely the showrunners wrote this ending with the intention of being shocking, but it passed into the realm of unbelievability. To many, it seemed much less like a carefully thought-out plan, and more like the writers had no idea who Gossip Girl was either, and just ended up making it Dan because it was the craziest possible answer.