15 Things We Still Can’t Believe Actually Happened on the Original ‘Gossip Girl’

I blame Dan Humphrey for giving me unrealistic expectations as a young writer. In Episode 11 of the first season, Vanessa (Jessica Szhor) gifts Dan with the ultimate Christmas present: getting published in the New Yorker at the ripe, young age of 16. Vanessa explains that she found a story in Dan’s desk and submitted it for him for the iconic magazine’s “20 under 20” fiction issue. (FYI, in reality, the New Yorker’s young writers issue is “20 under 40.”) In response, Dan asks, “This can’t be real, is this real?” Yeah, I can’t believe it either.

In a sweet twist, the story that Vanessa submitted was about the first time Dan saw Serena, titled with the date, “10/08/05.” Later on in the episode, Dan gives Serena the letter as her Christmas present (kind of self-centered, but OK). When she asks what the date represents, he says, “Well I was accidentally invited to a birthday party where I met a girl, and she only spoke two sentences to me, but I’ve never forgotten her.”

In perhaps one of the most shocking cliffhangers of the entire series, Serena tearfully tells Blair in Episode 16 of Season 1, “I killed someone.”

We later find out in flashbacks that after Serena slept with Nate (Chace Crawford) at the Shepherd wedding, she met up with Georgina (Michelle Trachtenberg) and their friend, Pete Fairman (Elan Moss-Bachrach). Georgina had plotted to film Serena and Pete having sex and set up a camera — but instead captured Pete’s overdose after doing cocaine.

Serena and Georgina fled the hotel room and Serena called an ambulance, but it was too late, as Pete died before the paramedics got to the hotel. When Georgina makes her appearance in Season 1, she reveals to Serena that she still has the tape and threatens to tell Dan, who she has started flirting with under the pseudonym Sarah. Serena then visits Pete’s parents for closure and eventually tells Dan the full truth in Episode 18 of Season 1.

One of the most didn’t-see-that-coming twists happens right off the bat in the first episode of Season 2, when we find out that Nate hasn’t been spending his summer in the Hamptons with Serena — but with Catherine Beaton (Mädchen Amick), a much older, married woman. At this time in the series, Nate would have been around 17, so this relationship was certainly sketchy at best (though that is the age of consent in New York). What’s more, when Nate’s father leaves town to escape going to jail, Catherine offers to pay Nate for having sex with her — and he takes the deal in order to save his family from bankruptcy.

Oh yeah, and later on in the season, Vanessa discovers that Catherine was also hooking up with her own stepson, Marcus (Patrick Heusinger). Gross!

Everything about “Gossip Girl” is always more interesting when Blair and Serena are fighting — and “New Haven Can Wait,” the sixth episode of Season 2, might just be the most heated it gets between the two besties.

College visit season is upon the students of Constance and St. Jude’s, and Blair is ready to trek to Yale and Serena to Brown. But when Blair tells Serena she couldn’t get into Yale even if she tried, Serena decides to ditch her plans and steal Blair’s dream: an invitation to the Dean of Admissions’ private reception. What ensues is completely bonkers.

Of course, while Blair waits for her interview with the dean (Byron Jennings), Serena is already done with hers and emerges in an extreme plunging neckline with the dean wrapped around her finger. During Blair’s interview, the dean seems completely unenthused and asks her to tell him something that isn’t included in her application. When Blair fails to come up with something, she falters and ends up kissing the cheek of the dean. Of course, Serena receives the invitation for the reception right in front of Blair, and so Blair defaults to blackmailing the dean’s assistant with an antique ceramic cat. But the battle is far from over — Chuck (Ed Westwick) reveals Blair’s answer to the dean’s famous reception quiz, “What person would you most like to have dinner with — alive or dead, real or imagined?” Serena plans to say Blair’s person of choice — George Sand — but Blair is already one step ahead, submitting Serena’s answer for her: Pete Fairman, the man she killed.

After Serena is forced to explain herself in front of the dean, the two confront each other outside and get into an all-out, physical fight complete with purse-throwing, hair-pulling and dress-ripping. Of course, they make up by the end of the episode, telling each other, “I don’t want to not know you” — and Serena still gains early acceptance due to her socialite status.

Little J aka Jenny Humphrey (Taylor Momsen) proves that she is all grown up by throwing a “guerrilla” fashion show during the New York Philanthropic Society’s annual gala.

In Season 2 Episode 9, Jenny and her new model friend Agnes (Willa Holland) devise the perfect marketing scheme for their new clothing line: bringing it straight to investors by crashing their party. But little does Jenny know, she is actually interrupting a night dedicated to the philanthropic efforts of Lily van der Woodsen (Kelly Rutherford) and Bart Bass.

After almost backing out, Jenny gets into the gala by pretending to be Lily’s son, Eric (Connor Paolo), saying that “sometimes they leave the A off” of his name. Somehow, that works, and Agnes bribes the gala’s sound guy by making him fall in love with her (again, how?). During the fashion show itself, the models tear through the gala, jumping on tables and dancing to the Ramones’ “Sheena Is a Punk Rocker.” Indeed, it’s all very punk rock, and surprisingly, Lily isn’t mad at Jenny — though the same can’t be said about Jenny’s dad, Rufus (Matthew Settle), who tries to get Jenny arrested. By the end of the episode, it is revealed that Jenny has run away from the Humphrey’s Brooklyn enclave.

Because Serena and Dan’s parents getting married didn’t make their relationship incestuous enough, they discover during Lily and Rufus’ wedding in Season 3 Episode 5 that they also share a brother — Scott Rosson (Chris Riggi). That’s right, Lily and Rufus had a child together when they dated in their younger years, but Lily gave him up for adoption and somehow kept the secret from Rufus, too. The two eventually go to Boston to talk with Scott’s adoptive parents, but they lie and say he died in an accident. However, Scott eventually tracks down Dan and pretends to be a student at NYU to get closer to him and learn about his birth parents — which is blown up when Georgina announces his existence to the world at the wedding. The look on Serena and Dan’s faces are priceless — how romantic!

File this under: things we didn’t see coming. It was unexpected enough for former Disney actor, Hilary Duff, to guest star on “Gossip Girl” — but who knew that her plotline would be so scandalous?

Duff played Olivia Burke, a movie star who decides to take a break from acting and attend NYU. Olivia’s roommate is none other than Vanessa, and after she bumps into Dan at a coffee shop, the two begin a relationship. Eventually, Olivia has to return to film the next movie in her “Endless Knights” franchise, so Dan and Vanessa embark on a mission to complete a bucket list of everything a person should do in college — which includes having a threesome. And, to make the whole situation even better, the scene is soundtracked by a slowed-down cover of T.I.’s “Whatever You Like.”

The constant back-and-forth between Chuck and his mom certainly served to humanize his character, but that doesn’t mean it was easy to follow.

We learn near the beginning of the series that Chuck’s mom died shortly after giving birth to him, an event that definitely had a large impact on his brooding, womanizing ways. But Elizabeth Fisher (Laura Harring) soon enters his life in Season 3 Episode 14, claiming to be his mother (under a pseudonym, of course). At first, the two are able to connect, but in the next episode, it is revealed that Elizabeth is in cahoots with Chuck’s conniving uncle, Jack (Desmond Harrington) to take over control of the Empire. Things escalate in Episode 16 when Elizabeth tells Chuck that she is in love with Jack, and tries to take his pain away by telling him that she is, in fact, not his real mother. But after Chuck and Blair’s car accident in Season 5, it is revealed that Elizabeth gave Chuck the blood to save his life, and by the end of the season, she finally admits that she is his real mother, proving it with a photo of her pregnant with him. Yeah, this whole situation probably didn’t help Chuck’s abandonment issues.

The Season 3 finale left viewers in complete shock when a) Chuck slept with Jenny, and b) Chuck went to Prague for the summer and got mugged and shot. The criminals demand Chuck’s money, to which he aptly responds, “I’ve got lots of money, I’m Chuck Bass.” But what they find — and turn out to really want — is the engagement ring Chuck purchased for Blair. The struggle then escalates, and Chuck is shot in the stomach and left in the street as David Bowie and Queen’s “Under Pressure” plays. Now that’s a cliffhanger.

This storyline is an emotional rollercoaster — and of course, also kicked off in the Season 3 finale. Georgina returns to Manhattan, nine months pregnant, and tells Dan that the baby is his from their previous brief hookup. Dan begins to prepare himself for impending fatherhood, with baby Milo being introduced in the first episode of Season 4. But then, Georgina runs away, leaving Dan with the baby. Over the next episode, we see Dan step up to the plate as a father, growing attached to Milo and even baby-wearing. However, Rufus eventually discovers that because of the baby’s blood type, there’s no way he can be Dan’s child. Georgina eventually returns and admits her deception, though I have to say I was a bit bummed to see father Dan fade to black.

Who could forget one of the show’s biggest romantic twists — when sworn enemies Dan and Blair shared a kiss? In Season 4, the two begin to form an unlikely alliance, bonding over film noir. And because she’s Blair and he’s, well, Dan, the two decide to keep their friendship secret. But people eventually start to find them out, and the secrecy of it all turns out to be more suspicious than just making their friendship public. After much stressing about the situation from Blair, she decides to put an end to their arrangement. But ever the romantic, Dan storms into her apartment and speaks the truth, “We kept us a secret because we were afraid there was something more.” In order to figure that out, the two agree on one kiss to test the spark — and boy, did they fly.

Before Blair and Prince Louis’ (Hugo Becker) marriage eventually crumbled, their wedding almost didn’t happen (maybe it shouldn’t have). In Episode 13 of Season 5, Blair leaves Louis at the altar after her emotional pre-nuptials conversation with Chuck was filmed and sent to Gossip Girl. In the video, Blair tells Chuck, “Not leaving with you is the hardest thing I’ve ever done,” so it’s definitely an explosive revelation. Though everyone and their mother was hoping for Blair to run away with Chuck that second, she eventually returns to the ceremony and goes through with the marriage. But Louis soon reveals that it’s all fake, telling Blair during their first dance, “There is nothing between us but a contract. Our marriage is all for show, and you’re going to put on the best damn show anyone ever has.” Ouch.

Ah, the ever elusive Bart Bass. It’s clear where Chuck gets his life mindset from, but even he may not be as cold as to attempt what Bart pulled off.

Back in Season 2, Bart died in a car accident, leaving Chuck parentless. But in Season 5, Episode 22, Bart comes back to life and explains to his shocked family members that he was forced to fake his death to avoid the entire family being killed. Needless to say, things get complicated as Bart reenters life in Manhattan — and attempts to get Chuck to flee to Russia in order to get Nate out of prison. (Bart had him arrested for fraud once he realized that Nate was aware of his own crimes.) Things come to a head on a rooftop, where Bart confronts Chuck and pushes him toward the edge of the building. Chuck punches Bart, who then lunges in his direction, throwing himself off the building in the process. Blair arrives just in time to see Bart fall, and the two make a run for it.

This list wouldn’t be complete without the show’s biggest reveal of all: that Dan is Gossip Girl. In the series finale, Dan decides to make amends with the rest of the group and reveals to them all that he was Gossip Girl through an article in Nate’s newspaper, the Spectator. Astonishingly, none of them are too mad at Dan for his actions (except for Rufus, and Blair for a hot minute), and they all sit around a table discussing how exactly he did it. After all, as Georgina remarks, Dan is “the only one who owns a hoodie.”

If anything, the appearance of Michael Bloomberg — who was the mayor of New York City at the time — in the series finale of “Gossip Girl” simply proves the amount of cultural power the show held. As the whole city finds out that Dan is Gossip Girl through the Spectator article, Bloomberg is shown saying, “I’m shocked! I thought it was Dorota,” referring to Blair’s housekeeper, played by Zuzanna Szadkowski. Honestly, I want to read a whole oral history on how that cameo happened. Kristen Bell, the voice of Gossip Girl, and “The O.C.” star Rachel Bilson are also featured reacting to the news — and of course, the whole show ends alluding to Gossip Girl living on despite Dan’s confession, taking us to the revival series. XOXO!