Gossip Girl ran for six seasons, chronicling the lives of teenagers from the Upper East Side, considered New York and Manhattan elite. Along the way, we meet other characters, such as their parents, enemies, and allies. However, for the most part, the TV show stays focused on Serena, Blair, Nate, Chuck, and Dan (the outsider). For many of the seasons, two other outsiders, Jenny and Vanessa also serve as the main cast.
Famously, the show was marketed with sexy and "scandalous" images of the characters in intimate scenes. In Season 2, the show actually turned bad reviews good. They took quotes from negative reviews, such as the Boston Herald, "every parent's nightmare" and paired them with pictures from intimate scenes, making them the marketing posters for the next season. It was very clever and ahead of the curve in the use of social media as outlined by Vulture. However, not everything about Gossip Girl aged so well.
Serena's Affair with a Professor
While Serena's attraction to Colin, her professor, happened before she reached that he was her teacher, it still continued. This set-up is very similar to Pretty Little Liars when Aria dates her English teacher. Likewise, it doesn't age well. The power dynamics between Serena and Colin are not fair, and Colin hides their relationship. Although he doesn't hide it well enough, he kisses Serena in his office, and they are caught on tape by another person.
Unfortunately, this incident wasn't the first teacher fling that Serena had in the series. Any show with the teacher/student dynamic hasn't aged well in recent years (and perhaps shouldn't have ever aged well in previous years).
Blair's Dad Rejecting Her After He Comes Out
It can be said that none of the parents are very active in their children's lives, apart from Rufus with Dan and Jenny, but this one especially feels off. Blair is close to her dad, perhaps even closer than she is to her mom.
Her dad discovers his sexuality, comes out as gay, and divorces the mother. For a while, he wants to break from everything and everyone associated with his previous life, including his adoring daughter.
Brooklyn's Status
Dan and Jenny live in Brooklyn and attend school with the Upper East-Siders. By Blair and others, Brooklyn is considered a crappy place to live, a place where poor people live. However, Brooklyn's status has altered throughout the years. It's regarded as a popular place to live; its population has grown, and it is getting even more expensive to live there.
Brooklyn may have been the place of the hipsters and the artists, but it may be harder for those creative individuals to live there now, at least not in a place as big as Dan and Jenny's.
Social Sphere Mainly Exists of High School Friends
This made sense when the teenagers were in high school; however, each character goes to college and then starts a career. While we understand that the elite group is especially close, and the outsiders are peripherally close, it doesn't make sense that they wouldn't have a larger social sphere.
We are talking about friends that stay, not those that are there for a couple of episodes and then gone (or are taken down by the group).
Gossip Girl and Bullying
The upper elite crowd reads and often contribute to Gossip Girl, a mysterious writer/blogger who shares the deepest and darkest secrets with everyone. Teens use the forum in order to bully each other and take revenge. The blogger also seems to do the same.
With the information about online bullying, this wouldn't sit as well with current audiences. If a similar blog were to happen today, characters would be searching for various ways to shut it down, rather than solely add to its content.
Rufus Dates Ivy, His Son's Previous Romantic Interest
Rufus usually stands out amongst the crowd of parents as one of the most loyal, smart, kind, and supportive. Even when he dates Lily and is brought into the elite world, he still maintains his integrity. So, why did it slip with Ivy?
Ivy was close to Dan's (his son) age, and she had a thing for Dan. She tried to be with him and get rid of the romantic rivals. An actress who pretends to be Charlie (Serena's cousin), she manipulates all of the elite group. In addition to Rufus dating one of his son's previous romantic interests, it also didn't age well how easily he was manipulated, especially with how he had been presented as a character and a dad from the beginning.
The disappearance of Vanessa and Jenny's Storylines
Vanessa (Dan's best friend and sometimes girlfriend) and Jenny (Dan's kid sister) were main characters at the start of the show, from Season 1 to Season 4. Later, they did return to guest in Season 6. However, they both faded from the storyline. The reason that this stands out is that both Vanessa and Jenny represent another world apart from the elite.
They represent artistic families with limited income, who struggle to make ends meet at times. When they both leave, Dan is the only main character who is an outsider, understands the financial struggle, and understands (and perhaps envies) the privileged life that he can't ever truly be a part of.
Chuck Assaulting Jenny and His Treatment of Women
Chuck, presented initially as an irritating and horrible guy, does grow throughout the show. His treatment of women improves. However, for many episodes and seasons, his treatment is truly awful. What he does would not fly with the #MeToo movement. A man born into power, he acts like he isn't accustomed to hearing no. When freshman Jenny gets invited to a fancy party, he isolates her from the group and assaults her. Luckily, both Serena and Dan find them before it gets too far.
The women in his elite group know of his reputation, but they aren't effective bystanders. When he gets ready to approach Jenny, he asks Blair's friends if there is anything about her on Gossip Girl. They respond back, not yet, but there will be with you are through with her. Additionally, in the same episode, he tries to start something with Serena, thinking because she was romantic with Nate, she would be with him. Chuck, in these moments, doesn't age well at all.
Dan as Gossip Girl
True, this twist wasn't always popular even when it first occurred, but it has aged worse. In the show, they spin it as Dan's big romance with Serena, that he wrote himself into her world. However, it reads as incredibly creepy and stalker-like in future viewings.
Dan, desperate to be with Serena, invents a gossip blog, masquerades as a girl, and convinces all to write to it so that he can spread damaging secrets around. Does this read as healthy? Not so much.
Chuck and Blair's Relationship
Now, we know that this is a controversial statement as Chuck and Blair are seen as the romantic sweethearts of the show. It is true that there were honest and beautiful moments between the two. Chuck seemed to really value Blair, and Blair could count on Chuck. However, there were also incredibly toxic moments.
For instance, Chuck offers his uncle a night with Blair in exchange for a hotel. He doesn't ask Blair, and she thinks that he turned down his uncle's offer. Then, later, she finds out the truth. The series ended with a couple of weddings, and one was Chuck and Blair. It's too bad; we wanted better for our Queen B.