If there's one thing the original Gossip Girl was known for, other than its scandalous relationships, it's keeping the audience on their toes. The series managed to surprise even the most seasoned TV watchers with plot twists, new pairings, and storylines that they didn't see coming.
With a huge cast of characters, and a setting that allowed for indulgence and glamour, the sky was the limit for Gossip Girl storylines. That meant there was never a dull moment, whether it was seeing the characters jet set to another country to escape their problems, or getting the reveal of Gossip Girl's true identity out in the open.
Serena Implies She Killed Someone
One of the running mysteries of the first season is just how out of control Serena was when she suddenly went to boarding school. There's a lot of hints as to what her life was like before the series begins, like her feelings for Nate, or the discussion of her substance use. What the audience isn't expecting though is for Serena to tell her friends she killed someone.
While Serena didn't actually kill someone (he died of an overdose), she still feels responsible. That storyline also doesn't just go away, but is revisited later in the series to pile more guilt on Serena. It's the kind of surprise for the audience that ups the stakes for the show. If Serena could be connected to a major incident like that so early in the series, it means that anything can happen.
Blair And Chuck Hook Up
While Blair and Chuck become the Gossip Girl couple to watch, that isn't the case in the start of the show. At the beginning, Blair is committed to Nate, despite the two of them having a lot of issues trusting one another - or even wanting to be together at all.
When Blair is upset and arguing with Chuck, the two end up hooking up in the back of Chuck's limo. It's a pretty shocking moment for the audience since, up until that point point, Chuck is the one member of the friend group the audience connects to least. He's there mostly to cause a little chaos, while Blair is a quick fan favorite. While Chuck never becomes the traditional good guy, it's his relationship with Blair that does set him on a different path.
Charlie Is Ivy
The only reason Charlie really being Ivy is so surprising is because this particular storyline of Gossip Girl has so many twists and turns it was like the audience was in a maze. Ivy is hired by Charlie's mother to impersonate her daughter so they can claim her share of the inheritance. Little does Ivy know that Charlie is actually in town too, but going by the name Lola, and dating Nate.
The paths of both young women, of course, cross, and the entire plan blows up in Ivy's face. Even more unexpected than this convoluted reveal, however, is that Rufus would then date Ivy. She's a peer of his kids - and pretended to be the niece of the supposed love of his life. The entire storyline involves a lot of surprising moments for the audience.
Dan Believes He Has A Child With Georgina
Georgina is a schemer from the moment she's introduced, so it's always a good time (full of conflict) when she shows up. When she blows back into town declaring that Dan is the father of her baby though, the audience is just as surprised as the characters.
Perhaps what's more surprising is that Dan initially believes her. There's nothing in Georgina's track record to indicate that she would tell him the truth. She's always ready to manipulate everyone, and Dan should have seen the real truth coming.
Chuck Is Willing To Trade Blair For A Hotel
Once Chuck and Blair are officially together, their romance has very high moments, but also very low moments. This is one of those lows. It marks one of the worst decisions Chuck ever makes in Gossip Girl, and that's saying something considering he's the king of poor decisions.
Chuck decides it's perfectly acceptable to give Blair to his uncle for the night in order to keep the hotel his family owns. It's a record scratching moment for the audience to process. The surprise stems from the audience thinking that Chuck truly loves Blair at this point in the story. It doesn't make sense for him to make that decision for her, or to put her in that position at all.
Vanessa Becomes Part Of Dan And Olivia's Relationship
Hilary Duff ing Gossip Girl in one of her first mature roles is already a surprise for the audience, but in a bit of a meta twist, she stars in the series as an actress that is assigned to room with Vanessa in college who is taking a break from the spotlight. Her character Olivia ends up dating Dan, but their relationship goes in an unexpected direction.
When Olivia, Vanessa, and Dan are trying to squeeze in as much of the college experience as possible, they decide to spend the night together. Not only does it shock the fans, but it also leads to friction in all of their relationships. Olivia and Vanessa have a hard time being friends, Vanessa and Dan see a strain in their friendship, and Olivia no longer wants to pursue a relationship with Dan when she realizes he and Vanessa might have feelings for one another. It's a big shakeup in the series that comes out of nowhere.
Chuck Is Shot In Prague
When Chuck and Blair hit one of their many rough patches, he doesn't just lose himself in another country to forget about her. He actually gets lost thanks to a couple of people mugging him, stealing the engagement ring meant for her, and shooting him in Prague.
While Gossip Girl is no stranger to dramatic relationship storylines and squabbles amongst its main characters that could lead to betrayal, violence isn't something the show delves into much. Chuck getting shot is a huge departure from how the series would usually dangle cliffhangers in front of the audience, and having it happen at the end of the season leaves the audience hanging on by a thread to find out if he survives.
Dan And Blair Have A Relationship
When the series begins, no one would expect Dan and Blair to find any common ground at all. As their love lives and friendships crumble in the later seasons though, they find and solace in one another - and discover that they have more in common than simply having Serena in their lives.
Putting Dan and Blair together brings the show a breath of fresh air. While it's impossible for them to work in the long term, seeing them go from rivals to friends to love interests makes for one of the most interesting (and fun) arcs of the show. Blair discovering that the heroine of his novel is based on her instead of Serena is certainly a standout moment for the audience.
Dan Is Gossip Girl
Fans spend the entire run of the show analyzing just who Gossip Girl could be. It's always presented that Gossip Girl is out to get Serena and Blair. This person has a vendetta. That's why it's such a shock when Dan confesses to being Gossip Girl - and that he told his little sister the truth before she was run out of town.
Though there are clues that point to Dan as Gossip Girl, the same could be true of any of the main group of characters. It doesn't make sense for a lot of the audience that Dan would be the person tormenting Serena at every turn when he cares about her so much. It's a hard pill to swallow that the role of anonymous internet bully is all part of what helps Dan become the writer he wants to be.
Serena Ends Up With Dan
If Dan being Gossip Girl is surprising, it's even more surprising then that he gets his happily ever after with Serena. Serena, who is Gossip Girl's main target for years, just forgives and forgets what Dan puts her through.
Serena and her friends spend so long trying to unmask the person tormenting him that it's almost a let-down for her to just brush it aside as he tells Chuck and Blair the truth. It's true that she finally ends up with someone who is always going to be laser focused on her, but at what cost?