Hey Upper East Siders, Gossip Girl here...

Lets take a deep dive into new york citys most scandalous teens.

Sep 24, 2024

From Kristen Bell’s amazing voice-over work to the questionable fashion choices the Manhattan elite seem to be wearing to lunch, it wasn’t going to be long before I started posting about the hit CW show. I’ve just finished the show, and in this potentially one-off post, I’m going to spill. Spill my opinions on the characters, that is.

Side note: the HBO Max reboot never screamed out to me, but after watching the original for the first time and seeing how in touch it was with the 2010s zeitgeist, I want to see how well Gen Z was written, so watch the space. If you’ve already watched it, do you think it’s worth my time?

Little J (Jenny Humphrey)

The award for the most over-hated character in the show goes to little J herself. I personally loved Jenny, and not just because i’m obsessed with Taylor Momsen. sure, she was annoying, but she was the youngest character in the show, teenagers are all the most annoying people on the planet!

Jenny always had the wildest storylines. all she wanted to do was go to fashion school (“Dad, I’m not your little girl anymore”- Jenny Humphrey, at the age of 15), but she was a busy girl. She dated Damien, the much older drug dealer, and helped sell drugs with him. She leaves home and quits school to start her own fashion line- which ends with her business partner (a literal other 15-year-old) burning all her designs and leaving Jenny homeless. She spent multiple seasons trying to get with Nate, no matter what the cost, and lost her virginity to Chuck before being kicked out of Manhattan by Blair. She added to her own drama by sending some of the messiest gossip girl blasts possible, including but not limited to the photo of Serena and Dan in bed together and revealing to everyone that she slept with Chuck (Talk about self-sabotage.) And the moment where she exposed Vanessa, literally, by getting her to wear the sheer dress in front of everybody. Maybe she was the worst, but I support women’s wrongs.

She also had the most unique style of all the New York elite, from season 2 onwards, she was synonymous with the bleached blonde hair, dark, heavy eye makeup and grungy outfits, leaning much more into Momsen’s own aesthetic and style. Little J, you may be hated by the masses, but to me, you will always be famous.

Golden Boy (Nate Archibald)

The Man who never sent a single tip to gossip girl, who went from the stoner lacrosse player to politician. Nate was basically just a good guy. He dated almost all the main female cast, as well as having a major thing for MILFS (but who wouldn’t want to date Elizabeth Hurley, tbf). despite being the biggest heartthrob of the cast, he was the only one single by the end of the show, whilst all his major love interests got their own happy endings. maybe it's the only real example of nice guys finishing last.

Documentary Girl (Vanessa Abrams)

Vanessa is most likely nobody’s favourite character on the show. Used as a foil, alongside Dan and Jenny, to the uber-rich Manhattan teens, V was the ‘other’ member of the group. she wasn't at school with any of the core characters; she didn't fall into the wealth of the Upper East Side like the Humphreys did and was only connected to everyone through association. She was always stuck in a different love triangle, normally with Nate and Jenny or Dan and Serena, (and that one time with chuck which was random.) but ultimately left at the end of season 4 without any romantic relationships after burning all her bridges with Dan.

Disliked by Serena and Blair, basically from her first appearance, Vanessa is introduced as Dan’s childhood friend. although she wasn’t at Constance/St. Judes, with the other characters, by season 3, she got integrated into the characters’ lives more when she attended NYU with Dan, Blair, Georgina and briefly, the Humphry/Van Der Woodson sibling Scott. She begins a relationship with Dan after one of the most bizarre moments the show had, in which she has a threesome with Dan and Hilary Duff (aka Olivia, dan’s famous girlfriend of a couple of episodes). in this same storyline, the 3 of them are involved in the creation of a Lady Gaga musical based on Snow White, something so awful that my writing cannot do it any justice, so I will just link it down below. She and Dan date on and off for a while, but ultimately, her hatred of Serena is the downfall of their relationship time and time again.

Vanessa ends her stint on the show by backstabbing Dan and publishing his book without his knowledge, similar to how she publishes one of his stories in The New Yorker in the first season. She knows the book will change all the relationships between the group, but her hatred overcomes any level of sympathy she could have for any of the people she has surrounded herself with for the previous four seasons. She is only seen again in the series finale, shocked at gossip girls’ identity.

The Bass-tard (Chuck Bass)

He’s Chuck Bass. The Bass-hole, Bass-tard and any other insults they could sneak into a network TV show. The guy written for you to despise at the start of the show, the wealthy heir who can have anything or anyone he wants. he’s manipulative, vengeful and pretty unlikeable. Always dressed in his best, living a life of luxury in hotel suits and being able to afford literally anything, hes the most elite of new yorks wealthy teens. He undergoes a lot of character development across the show, firstly as he realises his feelings for Blair and after his father’s death (both times!). Storylines including his mother, losing Blair and the time Dan got him a dog show the more vulnerable side to Chuck, the side that makes you still want to watch his exploits. at the end of the day, The Chuck and Blair of it all is kind of the main draw of the show. After their on-and-off relationship, they finally end up getting married in the finale, getting their happy ending.

of course, Chuck has his fair share of wtf moments. He Sells Blair for a hotel, changes his identity after being shot in Europe, he buys a club whilst he is a junior in high school (okay Riverdale) and so many other ludicrous things if I listed them all we would be here for weeks. He leaves most fans divided; some love him, think his relationship with Blair is one for the ages, and say he is the best character on the show. others hate him, think his sexually inappropriate behaviours in the early seasons are unforgivable and totally just don’t understand the hype. But he is, without a doubt, the core of the show.

The It Girl (Serena Van Der Woodson)

Spotted at Grand Central, bags in hand: Serena van der Woodsen. Was it only a year ago our It Girl mysteriously disappeared for "boarding school" and just as suddenly she's back? - Gossip Girl 1x01

She makes questionable life choices, has questionable fashion moments, and has the most questionable taste in men. But she’s the reason for gossip girl itself; she’s the it girl of Manhattan. SVDW herself, Serena Van Der Woodson.

She returns to New York at the start of the series, a former party girl with an insane past. at the age of 16, she has already:

had a pretty bad drug addiction
watched a man overdose and die, feeling responsible
slept with her best friend’s boyfriend
tried to have a relationship with a teacher at her boarding school, ending up with him going to prison.

She walks in fashion shows, is on the cover of magazines, and is repeatedly swarmed by paparazzi, the true socialite of the show. Despite her ‘it girl’ status, she is only the ‘queen bee’ at school for a short period, knowing it is truly only Blair’s position to hold. Serena is also wildly troubled, shown throughout the show. Her substance abuse is shown multiple times when she goes ‘off the rails’, she is drugged by Juliet in season 4, leading to her overdosing and ending up in a rehab facility. Her earlier storylines display her abandonment issues as she tries to locate her father, who left years prior. She is messy, always trying to hide a part of her past from whoever she is dating. some people think she’s too whiney, too annoying and unlikable- but she’s really just a flawed female character.

She has a brief moment of being gossip girl herself, in the later seasons, without even knowing that gossip girl was created just because of her. its queen shit, shes an icon, she is serena van der woodson.

Blair is one of my favourite characters in the show, being far more manipulative than you could ever imagine by looking at her, having so many troubles and traumas as the show progresses, always having the snarky, witty one-liner, and always dressed to perfection. I love her. The girl has dated multiple royals; she is almost literally a Queen B. Speaking to her ‘darker’ more manipulative side, she could be considered a much richer version of Rachel Berry from Glee, my girl Blair would definitely send a threat to her status to a crack house (yes that happened on glee).

despite being destined to be with Chuck, Blair’s romance with Dan in the later seasons was well-received by fans. both of them being pretentious classic film nerds, into art and literature, was a stroke of genius. you knew they would never work out, but the time they were together was enjoyable, and seemed good for both the characters, opposing Blair’s relationship with Prince Louis, which was genuinely hard to watch.

Blair also had a unique narrative device other characters didn’t, the show would often show her dreams (or nightmares) all of which were based on classic Hollywood films. It is truly giving main character energy.

Blair as Audrey Hepburn in Breakfast at Tiffany’s - Gossip Girl 1x04

Lonely Boy (Dan Humphrey)

Gossip girl himself. I loved Dan at the start of the series; he was the easiest of the main characters to support. I thought he and Serena were amazing when they first started dating, but found everything to get more complex after Lily and Rufus became a couple. As the show went on, Dan became less of a likeable protagonist, and by the final few episodes, I found him unbearable. He wrote a book about some of his closest friends and was so unbelievably cruel about them. if you can’t recall, in the book he wrote- Nate and Eric were merged into one character, telling Nate (his best friend) he wasn’t worthy of having a fully fleshed character; he wrote that the character based on Chuck committed suicide, and it took days for anyone to find out because no one cared about him and wrote Serena as a completely vapid selfish party girl, something she was trying to prove she was not. In the final season- he ends up completely removed from the group after reiterating this information in a series of articles. He writes so cruelly about Serena in the penultimate episodes, i genuinely thought they would have no chance of getting back together. before the big reveal in the final episode, Dan has alienated everyone and has become the cruel, Bart Bass-like man he had spent the previous 6 seasons hating.

He should have never been gossip girl and I will stand by that. framing it as a love letter to Serena was ridiculous and I cannot believe how quickly he was forgiven for it. he gets the happy ending with Serena that he honestly did not deserve, and as much as I loved him for the first 4 seasons, he became my least favourite by the show’s conclusion.

I stand by the fact Gossip Girl should have been Dorota or Eric. I will not change my mind on this.