The revelation that Dan "Lonely Boy" Humphrey was Gossip Girl all along was a fitting end to the show, in the sense that it was an incomprehensible mess best enjoyed as self-parody. Co-creator Stephanie Savage has claimed that Dan as GG was always the plan, and that the pilot even had to be recut because one sequence seemed to make the twist too obvious.
But unless the writers conceived of Dan as a sociopath from day one, this just doesn't fly. Thematically, it's elegant—Dan was the ultimate pseudo-outsider, wanting to believe he was better than the Upper East Siders while secretly longing to be one of them. Dan literally writing himself into their narrative, penning snarky commentary on his relationships with Serena, Blair, et al while playing the innocent nice guy, is a potentially amazing antihero story.
That's not the story Gossip Girl ever committed to telling though. The show wanted to paint Dan both as a sensitive hero who deserves to get the girl(s), and as a master manipulator who's basically Brooklyn's answer to The Talented Mr. Ripley.
So is this actually a psychological thriller about a teenage sociopath with dissociative identity disorder? Let's take a look at 11 of the weirdest Dan Humphrey/Gossip Girl cross-sections.
1. When he's shocked by this GG update about the masked ball (Season 1, Episode 6, "The Handmaiden's Tale")
Dan is visibly surprised to read a Gossip Girl update saying that Serena's looking for a date to the masked ball, and decides to blow off his plans with Vanessa to go and surprise her. But…you wrote the post, weirdo. Why are you pretending to be shocked when you're alone in your kitchen? The exposed brick doesn't care that you're Gossip Girl.
Side note: This is also the episode where Vanessa comes back to town and gets all self-righteous about her former hipster bae Dan now being into the Upper East Side scene. "You hate this world!" she yells, after finding out he snuck into the masked ball. So Dan's childhood BFF has no idea that he has any interest in the scandalous lives of Manhattan's elite, let alone that he's Gossip Girl. Something ain't right here.
2. When he outs Serena for buying a pregnancy test (Season 1, Episode 13, "A Thin Line Between Chuck and Nate")
Once again, Dan looks shell-shocked by a Gossip Girl blast—though this time Jenny and Rufus are there, so at least he has an audience to make feigning shock worthwhile. But the blast shows Serena, who is Dan's girlfriend at this time, buying a pregnancy test, thus sending the entire school (and Dan's dad) into a tailspin. Why would Dan ever do this?
Oh, and then there's this gem about Blair later in the episode:
"Looks like the Virgin Queen isn't as pure as she pretended to be. Who's your Daddy, B? Baby Daddy that is? Two guys in one week? Talk about doing the nasty, or should I say being nasty?"
3. When he spreads rumors about his 15-year-old sister's sex life (Season 1, Episode 16, "All About My Brother")
On one level, you have to respect Dan's commitment to the Gossip Girl persona here. But the way he—as Gossip Girl—talks about his 15-year-old sister in this episode is downright unsettling:
"Breaking News–Asher Hornsby overheard bragging that Little J swiped her V card at his register. Didn't anyone teach you, Little J? You shouldn't give away the ending if you want him to pick up the book again."
And then, a few scenes later…
"Looks like Little J didn't spread her legs after all. She spread lies instead."
Dan Humphrey: redefining the worst since 2007.
4. When he outs Dan and Serena's secret reunion (Season 2, Episode 3, "The Dark Night")
So Dan and Serena get back together at the start of season two, but Dan really wants to keep it a secret. Serena persuades him that they should reveal all at Blair's upcoming party…but then a Gossip Girl blast comes out showing the two of them kissing. Maybe Dan decided to pre-empt Serena's plan out of pure spite, but what kind of a petty asshole would…okay, yeah. Never mind. This one makes total sense.
5. When he outs Dan and Serena's faux-incest (Season 2, Episode 15 "Gone With The Will")
Lily and Rufus's love child was all-around one of the show's worst storylines, and it led to one of the most egregious "Dan as Gossip Girl" fails. After learning about their long-lost sibling, Dan and Jenny understandably decide to keep it quiet—but Gossip Girl takes the first opportunity to spill the incestuous beans, making Dan and Serena's barely reconciled relationship super awkward.
The blast goes like this: "It seems D and S share a sibling! While I'm always a fan of star-crossed lovers, at least Romeo and Juliet didn't share DNA!"
…At this point Dan is actually just trolling Serena, right?
6. When he outs himself as a cheater (Season 2, Episode 17 "Carnal Knowledge")
Remember when Dan had that brief, creepy affair with a teacher at Constance, and Gossip Girl posted the rumor before they even officially hooked up? Admittedly, Dan and Serena had a lot of other issues at this point, but the "hot for teacher" rumor was the final straw.
The only explanation that makes sense is that Dan has a Mr. Hyde-esque alter ego who really hates Serena and is constantly trying to sabotage their relationship. Or he just wants to make himself look like a stud. Either way, ugh.
7. When he reveals his sister is a drug dealer (Season 3, Episode 20 "It's a Dad, Dad, Dad World")
When it comes to Dan and Jenny, the writers tried to cover themselves in the series finale by including a line claiming that Jenny knew he was Gossip Girl all along. Jenny was a total social climber, second only to her brother in her desperation to get on the inside, so she'd definitely use the GG access to her advantage. But being outed as a drug dealer did not help her social standing in any way, and she's clearly really upset about it in this episode. Thanks for nothing, bro.
8. When he creates a Dan vs. Nate poll (Season 4, Episode 2, "Double Identity")
A poll specifically asking whether Serena should choose Dan or Nate. This might make sense if Dan had won in a landslide, because you know he'd be all about rigging it. But in the end, nobody wins, because Dan and Nate both passive-aggressively start dating other girls before Serena gets back from Paris. So what's in this poll for Dan, other than the probability of public humiliation when Nate inevitably beats him?
9. When he is shocked about Georgina's beachside shenanigans (Season 4, Episode 3, "The Undergraduates")
Once again, Dan is stunned by a Gossip Girl update that reveals Georgina's chillin' on a beach while he's taking care of her baby. And once again…he is alone in his kitchen feigning shock. Like really though, does he think the bricks have eyes?
10. When he spread the news of Serena's overdose (Season 4, Episode 10, "Gaslit")
Serena wakes up in a seedy hotel room after an overdose, and Dan is the only person who believes her when she says she's been framed. Touching, right? Mm-hmm. Then comes this Gossip Girl blast:
"Afternoon, Upper East Siders. Were your dinners as filling as mine was? Hope not, because have I got some dessert for you. With sugar on top. It seems everyone's favorite party girl fell off the wagon and landed right in rehab. Good luck getting a Lohan-dle on things, S. From the looks of it, you've got a lot to recover from."
In the same episode, Dan makes a self-righteous speech to Lily about how he "sees the good in Serena," and is clearly super-enjoying his hero status in comparison to everyone else in the room. DIE IN A FIRE, DAN HUMPHREY. (Or maybe just seek psychiatric help because this is actually getting a little scary.)
11. When he blasted out a video of Blair confessing her love for Chuck (Season 5, Episode 13, "G.G.")
This one actually defies the laws of physics. So Dan is at Blair's clearly doomed wedding to douchey prince Louis, standing right up at the altar, definitely not typing. Right as Blair finishes her walk up the aisle, a Gossip Girl blast comes out with a video of Blair confessing her love for Chuck. That conversation happened about five minutes earlier, so unless Dan did some incredibly speedy typing and auto-publish scheduling, he must have a Gossip Girl intern doing the posting for him.
The bigger question mark is why Dan would want to publicly humiliate Blair, a woman he claims to love. Oh, right—because he's a terrible excuse for a human and has already been pulling that nonsense with Serena for five seasons. Right after ruining the wedding and letting Chuck take the blame, Dan whisks Blair away and Nice Guys her all the way to the airport, presumably cackling under his breath like the supervillain he is.
…How did this show not end with Dan Humphrey being thrown into a volcano?
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