Upper East Siders.

Serena van der Woodsen (Queen S) People compare her character with Josh Schwartz’s original it-girl creation, Marissa Cooper, stating that Serena “seems to have it all, but in addition to a party girl reputation, dark family secrets and a disregard for high society, Serena one-ups the sulky Coop with a history of BFF betrayal.” [2] Jason Gay of Rolling Stone describes Serena as “the bad girl gone good(ish) who serves as Gossip Girl’s wobbly moral compass.” He added praise while describing her early strained relationship with Blair, stating, “Lively’s Serena is a former queen bee who mysteriously disappeared from campus, only to return and find her spiteful ex-best friend, Blair (Meester), in charge.”[3] With regards to her character’s direction in the show, actress Blake Lively commented on her character’s adventurous storylines during an interview with NYLON saying “I feel ridiculous at times with her, because I’m, you know, killing someone or marrying someone, but I look like me. I’m like, ‘Oh, this is absurd.’ ” [4] [5] [6] Vogue magazine considers Lively’s upbringing to be advantageous to her character background and finds her “dazzling and worldly and optimistic”. Her mother, a former model from Georgia would dress her differently and her differing fashion choices drew the attention of her classmates from the L.A. private school she enrolled in. “It was the only school where people were just downright mean to me,” Lively stated. “They would make fun of my clothes because I dressed differently than the other kids.” [7]

Blair Cornelia Waldorf ( Queen B ) In the first book, Blair is introduced as a privileged, comically vain overachiever.[6] She is described as an alluring brunette,[7] and occasionally models her appearance and demeanor after famous actresses, including Marilyn Monroe and, frequently, Audrey Hepburn.[8] In early novels, the character is also written as bulimic. Blair is largely motivated by matters surrounding family, romance, and ambition. However, her tendency to overachieve can lead to feelings of paranoia, with dramatic or comic results. In a review for The New Yorker, Janet Malcolm remarked that Blair’s issues made her “both a broader caricature and a more real person” than the other Gossip Girl characters.[6] In a 2009 interview, Gossip Girl creator Cecily von Ziegesar claimed to identify with Blair the most. “She is so unpredictable and dramatic. Such a bitch, but we understand why she is a bitch and we like her anyway”.[9]

Nathaniel Archibald ( Nate ) he is a “WASP” lacrosse player at the elite St. Jude’s School for Boys. His mother, Anne Archibald, is a French socialite, and his father, Captain Archibald, is a former Navy captain and a wealthy banker. Nate’s friends are Anthony Avuldsen, Charlie Dern, and Jeremy Scott Tompkinson, and his best friends since childhood are Serena van der Woodsen and Blair Waldorf, who is also his on and off girlfriend. Nate’s family resides in a stately townhouse off Park Avenue on the exclusive Upper East Side of Manhattan in New York City, and his mother’s French socialite family owns a summer chateau in Nice. He is a fan of sailing like his father, and wished to do that instead of attending Yale with his girlfriend Blair, although he expressed interest in attending Brown University. At the end of the series he sails around the world with a friend of his father’s, Captain Charles ‘Chips’ White to avoid getting in between Blair and Serena again. In I Will Aways Love You, on break from Deep Springs College, Nate chooses Blair in part I and then Serena in part II.

Daniel Humphrey ( Dan ) lives with his father Rufus, and sister Jenny in Brooklyn. He is tall and pale, and is quite neurotic. He enjoys drinking coffee. He is considered to be an intellectual when it comes to writing and literature, and was in fact an intern for The Strand one summer. His favorite past time is writing on his black journals. He goes to St. Jude’s Preparatory with Chuck Bass and Nate Archibald. In the first part of the books, he is in love with Serena Van Der Woodsen because of a party he threw at their apartment before he went to boarding school. When Serena returned to the Upper East Side, she was ostracized by her peers, so she made friends with Dan and Jenny. Dan later realizes that he has feelings for Vanessa, so he begins a relationship with her. They have a fight when a video of Jenny without her pants is leaked onto the internet, and she apologizes by sending his poem to the New Yorker. Dan gets published, and they make up. He gets an agent called Rusty Klien who claims he is “the next Keats.” Rusty introduces Dan to Mystery Craze, a novelist. They hook up on stage at a poetry reading which Vanessa sees, effectively ending their relationship. He gets an internship at Red Letter, which he leaves once he realizes they don’t want him there for his talent. He gets back together with Vanessa after he sends her a small, pink singing toy from Japan to film, and at a party at her house, a band called The Raves make him their new front man because of his poems, which they thought were lyrics. He hooks up with one of the instrumentalist’s wife, which ends his stint with them. He later meets Bree while working at The Strand one summer while he was still dating Vanessa. Dan explores his sexuality later in the books by starting a relationship with his co-worker in the Strand by making literary salons with him, which were, in actuality, giant orgies. He breaks up with his co-worker because of Chuck, and he realizes that he truly loved Vanessa. He went to The Evergreen State College for bachelor studies.

Vanessa Abrams ( V ) Described as sullen, with a shaved head and black clothing, Vanessa is a budding filmmaker and Constance student on scholarship. Her dream is to one day attend NYU and major in film. Her hippie artist parents live in Vermont but allowed her to move to Williamsburg, Brooklyn to live with her sister Ruby. In the first books, she stays away from Blair Waldorf and Serena van der Woodsen’s social scene, resenting the Upper East Side way of life and preferring the company of Dan Humphrey, her best friend, and her sister Ruby. She has had a huge crush on Dan ever since they met on a fire escape when they were both locked out of a party, but Dan had always been too in love with Serena van der Woodsen to realize it. Dan and Vanessa finally get together in the second book, but break up when Dan cheats on her with a writer named Mystery. Vanessa is very fond of making dark films and spends most of her time filming people and objects. She later becomes friends with Blair Waldorf, and they become short-lived room mates. She takes much from her, becoming more open to the Upper East Side way of life and later semi-adapting to Blair’s sense of fashion (though she once quipped that she would not be wearing snakeskin Manolos anytime soon) She begins a relationship with Aaron Rose, Blair’s stepbrother, only to cheat on him with Dan come graduation. Dan and Vanessa once again become a couple, but with Vanessa taking a job as an assistant for Ken Mogul (and later a babysitter) and Dan cheating on her yet again with a leggy blond named Bree, they break up. Dan has a period of crisis when he thinks that he is gay after kissing a guy at work, but Vanessa stands by him. She agrees to move in with Rufus Humphrey (having been kicked out of her apartment by her sister Ruby and her new fiance Piotr) during the fall when she goes to NYU. Dan turns out to be straight, and they spend the time they have together before college being a real couple. In I Will Aways Love You, it was revealed that Vanessa grew her hair out.

Jennifer Humphrey ( Little Jenny ) Jenny is the daughter of Rufus Humphrey, an editor for beat poets whom has never been published himself, and Jeanette Humphrey, who ran off with an European aristocrat. She has an older brother Dan Humphrey, who is an aspiring writer. Jenny is a student at the Constance Billard School for Girls, a small, elite, all-girls school located on the Upper East Side, which Serena Van der Woodsen and Blair Waldorf also attend. In the book series, Jenny Humphrey is described as a short, well endowed brunette while the television show depicts her as tall, skinny and blonde. In the Gossip Girl prequel It Had To Be You, Jenny is noted for having a rather flat chest until she begins taking breast enlargement supplements, which turns out are the cause of her double D cup size. Jenny is the protagonist in the book series, The It Girl, which shows her new life, after she gets expelled from Constance Billard, and starts at Waverly Academy in upstate New York. In The It Girl, Jenny tries to reinvent herself as a “popular and sophisticated city girl” and leave behind the person she was at Constance. When Jenny arrives at Waverly, she finds the students even more attractive, athletic, and intimidating than she imagined. Jenny then meets her two new exceptionally beautiful and popular Junior year roommates: lithe and blonde Southern girl Callie Vernon, and red-headed, green eyed, and sophisticated New Jerseyan Brett Messerschmidt. She quickly learns that she has replaced their old best friend: extremely attractive and notorious Tinsley Carmichael. Jenny can’t help but feel that sleeping in such a lucky bed must rub off.

Charles Bartholomew Bass Jr. (Chuck)  In the Gossip Girl novels, Chuck has a series of flings with male and female characters across the course of the series. Chuck’s role is initially that of an antagonist to the main characters. Chuck resides with his family at the Plaza Hotel on the Upper East Side and attends school at the Riverside Preparatory School for Boys on the Upper West Side, along with scholarship student Dan Humphrey. Chuck is largely friendless, but is tolerated by the others because of his family’s enormous wealth. He is described as having flamboyant fashion sense, with a penchant for scarves. Lazy and vain, Chuck’s only interests are sex and money, and he is frequently chided by his father for lacking ambition and performing poorly in school. Following flings with numerous females and males, his only serious relationship comes near the end of the series, when he begins dating Blair Waldorf, a self-obsessed luxury loving teenager. In the twelfth book in the series, Gossip Girl: It Had To Be You (2007), Chuck is rejected from colleges because of poor grades and is sent to military school by his father. When next mentioned in Gossip Girl spin-off The Carlyles (2008), it is stated that Chuck never showed up to military school, and his whereabouts thereafter are unknown. In the thirteenth Gossip Girl novel, I Will Always Love You (2009), it is revealed that Chuck went off to Deep Springs College in California and returned a changed man, and to have dated main character Blair Waldorf in Oxford, England for a year.