Imagine my joy when I found myself with ample free time this winter break—perfect for being reintroduced to Blair Waldorf and the drama of the Upper East Side. When I first watched the show at the age of 15, I didn’t really pay much attention to the hipster from Brooklyn, who actually ended up being the bane of my existence as I’ve re-watched it over and over again. The more I watch it, the more I realize that Dan Humphrey, for a lack of a better phrase, was a flaming asshole.
1. Dan slut-shames Serena.
In Episode 2, after one date with Serena, he goes all “Lonely Boy” and shames her, stating that he thought she was different. However, we obviously later find out that Dan was Gossip Girl all along, meaning that he must have already known that Serena and Nate had sex. Not to mention, this all happened before Serena was even introduced to the Joe Goldberg of the Upper East Side.
2. Dan has sex with Blair even though he was previously with Serena.
I don’t know how any of this got past the writers’ room, considering the fact that Dan and Blair being together was quite possibly the worst couple in the show. He claims he loves her, but posted her entire diary on Gossip Girl. Later on, he sabotages Blair’s marriage with Prince Louis by projecting a tape of her saying that she’s in love with Chuck… and then stands in the way of Blair and Chuck getting married?
3. Consistently posts terrible things about his sister Jenny.
Dan puts Jenny on blast for losing her virginity to Chuck, who once tried to rape her. Throughout the series, he then becomes closer and closer to Chuck… Even though he tried to rape his sister? Before that, Dan pretends to be friends with Chuck, finds out that his mother died during childbirth, and proceeds to use his secret to write a story.
4. He’s different, he’s not like other boys.
Throughout the series, Dan purposefully sets himself apart by being obsessed with wanting to go to an Ivy League school. He pretends to hold a moral high ground over Chuck and Nate but ends up being much worse than them due to the fact that he wouldn’t date Vanessa or Georgina because they aren’t Serena or Blair — which means he’s just like them. He shames Jenny for wanting to be like the Upper East Siders, even though that’s what he wants most of all — isn’t that the purpose behind him squirming his way into Serena’s life?
5. He pretends to be the good guy.
I don’t know what much more I can say about this — considering he betrayed everyone in the series at least once. As he betrays them, he continues to question why he is alienated from the rest of the crowd, even though he never admits to being wrong. The entire basis of the show is based on his five-year-long power trip.
6. He’s a terrible writer.
Dan had little to no imagination and went as far as naming Serena “Sabrina” in his story. If that wasn’t offensive enough, he called Chuck Bass “Charlie Trout”. Other terrible lines include:
“Spotted: Dan Humphrey, shoeless and clueless.”
“Looks like World War III has just broken out — and it’s wearing knee socks”.
I can go on and on about Dan Humphrey. He’s the kind of guy who insists he’s a “good guy,” and constantly plays the victim card even though he’s actually just an asshole. People don’t dislike Dan because he isn’t an Upper East Sider or because he’s “different” – they dislike him because he sucks. He cannot and will not change or admit his faults, no matter how much he hurts the people around him. If someone could post a compilation video of him apologizing, maybe that would satisfy my intense need to see him punished. But then again, maybe not.