What is Gossip Girl? Gossip Girl is an anonymous blogger who sensationalized the lives of Manhattan’s Elite, think of it as a Fitzgerald novel but for the modern teenager. Before we had real gossip sites or easy access to the internet on our phones, Gossip Girl, jumped onto a growing movement of social media, or should we say establishing a need for it, and the need for bigger and juicer information, at a time when those things weren’t as readily available.

Gossip Girl became a phenomenon, influencing how we dress, behave, and our own social needs, but how did we get here? And how does the new series compare to our favorite Upper East Siders? Let’s delve into the background of the series and explore the first six episodes in this highly anticipated reboot.

How did the Gossip Girl Phenomenon Start?

So how did Gossip Girl come about? Well, it all comes from the mind of writer Cecily von Ziegesar, who attended the prestigious Nightingale-Bamford School where most of the inspiration for the characters, plots, and locations are taken from. The books, there are 13 in total with two spinoff series, centers around Blair Waldorf and Sarena van der Woodsen who are privileged teenage socialites attending the Constance Billard School for Girls, in the book we read about these young women who must navigate boyfriends, schoolwork and society’s pressures all while being exploited by an anonymous blogger only known as Gossip Girl.

The original book series was published between 2002 – and 2011, in September of 2007 the book would be adapted into a TV show and premiere on the CW network, after being picked up and produced for TV by Josh Schwartz, the man behind The O.C., and Stephanie Savage. The show would last for six seasons and change the way teenagers and young adults would interact with each other, dress, socialize and look at the world at large, with a passionate fan base behind it, it would only be a matter of time before a reboot would be on the horizon.

As an avid fan of the show myself, and September edging ever closer as my yearly re-watch of the show is about to begin, I have seen the show analyzed over the years, with people exploring the characters in-depth as well as what the world was like then. Also, it is always fun to play detective with other fans as you try and work out who Gossip Girl really is. I do hope that with time we will get to explore this reboot with that same passion and even compare the different shows.  

How do the Original and New Teens of the Upper East Side Compare?

Serena Van Der Woodsen is who the show and Gossip Girl blog is about, after returning from a year away at boarding school, she wants to have a more peaceful life, but that’s not possible on the Upper East Side. She is tall and slender, with long blond hair and a manic pixie dream girl vibe that most men lust after, she is the “IT Girl” of Constance Billard School. In comparison, we have Julian Calloway an “IT Girl” in her own right who is an Instagram influencer and whose entire life is controlled by her friends and the person she must portray to the world. In a lot of ways, they are similar but in other ways, they are very different, but both young women are on a journey of discovery. While Serena had Dan Humphrey and Vanessa Abrams who brought out the best in her while showing her the realities of the world outside her UES bubble, while Julian has half-sister Zoya and boyfriend Obie who are obvious avatars for Dan and Vanessa.

In Gossip Girl (2007) Blair Waldorf is the best friend of Sarena, although they have a very on-again off again friendship, they are more like sisters really. Blair is the Queen Bee of the Upper East Side and is determined to stop at nothing to stay in that position. She is short with deep brown eyes that match her hair and has the air of an old Hollywood film star about her. Her Gossip Girl (2021) counterpart seems to be that of Audrey Hope, who is the best friend of Julian and Aki’s girlfriend, she has a very Blair Waldorf vibe about her, but is she different from the former Queen Bee of the UES? We won’t truly know until we get deeper into the series, but the two are physically and stylistically, from the way they speak to their preppy style, similar. Is Audrey’s home life as dysfunctional as Blair’s? only time will tell.

Zoya Lott and Julien Calloway are half-sisters on their mothers’ side and have reconnected after finding one another in the Gossip Girl Reboot. But who is Zoya’s counterpart in the original 2007 series, this is a hard one to figure out, she has that Dan Humphrey vibe of being a writer and our window in but I would say she is more worldly and creative, meaning she leans more towards the character of Vanesa Abrams. Vanessa is the moral compass of the show, being a little more worldly than everyone else, she isn’t from the upper east side and hates anything to do with money and the corruption it causes, but as time goes on, she learns how to play the game, but this world just isn’t for her. She is too sweet for the manipulation that is needed to survive in this world and Zoya seems to have that about her too, they are also both quick to act before thinking when their feelings are hurt.

Dan Humphrey is our window into the scandalous lives of Manhattan’s elite in the OG series, he is from Brooklyn and attends St.Jude’s on a scholarship but that doesn’t stop him from becoming entangled in the lives of his classmates. As a writer and a fan of the novels of Fitzgerald seems like an almost poetic and unbelievable adventure doesn’t it? In contrast, we have both Zoya and Obie to fill this role in Gossip Girl (2021). Obie whose real name is Otto Bergmann IV has feelings for both sisters and comes from a family that is in property development. Aki, whose real name is Akeno Menzies, is an interesting character too, he is the bi-curious boyfriend of Audrey who is best friends with Obie and Max. 

Obie and Aki deal with many ups and downs while both being drawn to two individuals in their lives when it comes to romance, very much like Nate Archibald who spends most of his time entangled in love triangles. On the subject of Nate, he is presented as a good-looking, athletic, and all together dim-witted young man, but the more you get to know him the more you realize he is so much more. Not your typical jock he has secrets just like everyone else runs into some trouble with the ladies from time to time but has a heart of gold. These three men all are weighed down by the burden of expectation that has been thrust upon them by their families and just like Nate, Obie and Aki will hopefully go on a journey of discovery, finding their voices and carving their own paths in this world that aligns more with their beliefs.

Chuck Bass is a decadent, manipulative, and morally corrupt member of society, using his power, influence, and privilege to get what he wants, be that sex, alcohol, or drugs. He does grow up a lot during the original Gossip Girl series but that doesn’t stop him from being a questionable character and making bad choices. Max Wolfe would be more like Bass had he not grown up in the early 00s and had less supportive parents, the pansexual playboy of the group, who seems to be close with everyone while also being able to do his own thing. 

Jenny Humphry, who is the sister of Dan in the OG series, starts off wanting to be like the Blair Waldorf’s and Serena Van Der Woodsen’s of the world. Jenny goes from a sweet, naïve, and down-to-earth girl to an absolute monster, she is the cautionary tale of what wanting power and influence can do, it can destroy you and everything you hold dear.  There doesn’t seem to be a Jenny Humphrey counterpart in this series yet, but there is always time.

Luna La is best friends with Julian and Monet, acting as J’s stylist and M’s partner in crime while Monet de Haan is Julian’s social media manager, a partner in crime with Luna, and a strong, powerful representation of a young lesbian. Luna seems to have all the hallmarks of Penelope, the right-hand woman to Blair Waldorf. Luna and Penelope are both beautiful and privileged with a cutting sense of humor and will stop at nothing to achieve their goals while climbing to the top of the food chain.

Monet is similar in a lot of ways to Luna but is more vicious, headstrong, and self-sufficient while having a genuine interest in her own self-preservation. All these characteristics directly correlate to the conniving, highly intelligent and drama fuelled individual known as Georgina Sparks. Both keep everyone and the viewer at an arm’s distance away, with you never knowing what they are up to or who they truly are. Monat seems to be being set up as the villain of the piece and if she is anything like Sparks the upper East Siders will need to watch their backs.