Gossip Girl: 10 Things About Dan That Would Never Fly Today

Dan Humphrey is the Brooklyn boy portrayed as the ultimate outsider looking into the Upper East Side life in NYC on Gossip Girl. Through the course of the series, he gains access through “It Girl” Serena Vanderwoodsen and dates her throughout their high school years. His father Rufus marries Serena’s mother Lily and his access increases even more as the whole family moves to the Penthouse at the Plaza.

In season 4, Dan publishes a book called “Inside” with characters based on all the Upper East Siders in his life. With that success, his outside status as “Lonely Boy” ends, but it doesn’t all go his way. Through the ups and downs and his schemes to gain the access he always craved, Dan did many things that would never fly today.

10 Didn’t Report Chuck Bass

In the very beginning of the series, Dan’s little sister, Jenny, goes to Blair’s “Kiss On The Lips” party. While there, Chuck lures Jenny into an unwanted advance and attempts to assault her. Jenny gets away, but when Dan finds out, he punches Chuck and agrees not to get any authorities involved.

Today, that would never fly. No matter how rich the person is, if they attempt to sexually assault a child, most people (especially those in power on the Upper East Side) wouldn’t hesitate to make a report.

9 Outed Asher As Gay

At the end of season 1, Jenny is dating the very popular Asher and Dan catches him kissing another boy in secret. In an effort to take his little sister down a notch, he schemes with Blair to out Asher as gay at his own party. The Upper East Siders take it all in stride and Asher has his own way of attempting to retaliate.

While today’s teenagers would definitely still have issues with bullying in the LGBTQA+ world, someone outing someone out of sheer spite wouldn’t fly amongst most people, especially in the crowd that Dan and Blair ran with.

8 Broke Up With Serena Over Social Differences

The beginning of season 2 had Dan going to the Hamptons to win Serena back. Eventually, they decided that their worlds are just too different and they can’t stay together.

In today’s world, this would never fly. Social differences to do with money, with two people who both have great privilege and go to the same school, would likely not be an issue. Not to mention, at that point, Dan had many friends in the Upper East Side world and he was able to keep those relationships.

7 His Affair With Rachel Carr

During his senior year, Dan has an affair with his Shakespeare teacher, Rachel Carr. She’s not that much older than him and he is 18 at the time, so what happens is technically not illegal. But the whole thing spins out of control, with parents, teachers, and other students getting involved, and Miss Carr eventually is fired and moves back to her hometown in Iowa. This whole scenario would never fly today.

An 18-year-old legally hooking up with a teacher on his way out of school, especially with what happens after she is fired, wouldn’t have raised all the red flags that it did. If Dan is independent, an adult at age of consent, and the teacher no longer worked at the school, it is unlikely that there would be such upset over their relationship.

6 Dated Olivia In A Normal College Setting

The story arc where Dan dates famous actress Olivia (but doesn’t know she’s an actress) would never fly today. There were internet and cell phones then, but the world of the show doesn’t show a ton of social media use. There is Gossip Girl and that’s about it.

In today’s world, an actress with a hit movie series going to an Ivy League school like NYU would have been all over the place online. There would have been speculation about her acceptance, social media presence about their relationship, and the whole thing with her fake on-screen boyfriend would have been a much larger scandal.

5 Signed Milo’s Birth Certificate With No Paternity Test

In the beginning of season 4, Georgina Sparks showed up at Dan’s Brooklyn loft very pregnant and claiming the baby was his. They holed up after the boy was born in the loft during the newborn stage and Dan took on the role of baby Milo’s father without question. When Rufus and Lily meet Milo, they inquire about a paternity test, but Dan is adamant. In the end, it turned out that Milo wasn’t his, and getting him to sign the birth certificate was just another ploy by Georgina.

4 Helped Serena Escape From The Treatment Center

When Serena is involuntarily held after a forced overdose, Dan is the only one that believes her when she says that she didn’t actually overdose and the whole thing was a setup. He breaks her out of the Ostroff  Center, where she’s been committed, using a wild plan that shouldn’t have worked.

In today’s world, breaking someone out of a treatment center like that would likely have resulted in some kind of criminal charges, at least.

3 Wrote A Scathing Tell-All Book Without Permission (Twice)

The character’s in Dan’s book “Inside,” that comes out in season 5, are supposedly fictional. But the people in his life know who’s who and many others around them know too, implying that the characters were close enough for the book to do damage to their real lives.

Later on, in season 6, Dan teams up with Georgina to write a serial called “Inside Out.” It’s another scathing tell-all that’s damaging to all around him. In today’s world, he’d never get away with this and publishers would be skewered on social media for letting the works be published.

2 Terrorized Everyone As “Gossip Girl”

The show’s namesake is a website that is a character in itself – some fans might even say it’s the main character. Gossip Girl destroyed lives, caused arrests and jail time, spread all kinds of rumors that terrorized every character, and even led to a couple of deaths. The entity was not simply a reporter – Gossip Girl also stirred up stories and manipulated people to make them happen.

The series finale revealed that Dan was Gossip Girl and in today’s world that would never fly without serious consequences. Gossip Girl’s history was like a confession written over several years and yet Dan doesn’t face any punishment. Rather, he is praised as “giving everyone their start” due to Gossip Girl’s scandals.

1 In The End, He Wins Serena Over

Through all the ups and downs and the social differences Dan and Serena claim would always keep them apart, the series finale shows a time jump with the whole group at Dan and Serena’s wedding. They’re still from two different worlds, but Serena saw Gossip Girl as a “love letter” because it was Dan’s desperate way of getting into her world.

In today’s world, no one would see it this way and fans have lamented over Dan’s stalker behavior (fun fact: Penn Badgley’s next popular role is as stalker Joe in YOU) and how Serena could ever see it as loving.

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