Here’s the synopsis for Cecily von Ziegesar’s Gossip Girl: A Novel, the #1 New York Times bestselling young adult novel series, that was posted on Hachette Book Group:
Welcome to New York City's Upper East Side, where my friends and I live, go to school, play, and sleep--sometimes with each other.
S [Serena van der Woodsen] is back from boarding school, and if we aren't careful, she's going to win over our teachers, wear that dress we couldn't fit into, steal our boyfriends' hearts, and basically ruin our lives in a major way. I'll be watching closely...
You know you love me,
gossip girl
Gossip Girl, the CW television series, is based on the novels. The series was called “Mind-blowingly inappropriate.” by the Parents Television Council, “Very bad for you." by the San Diego Union-Tribune, “A nasty piece of work.” by the New York Post, and New York Magazine opined that the series was the “Best. Show. Ever.” Along with seductive images of high school students, those reviews were proudly used by CW in advertisements for the television series. However, I would argue that the young adult novel series is inarguably more salacious.
In preparation for my book From Gossip Girl to Pretty Little Liars: A Study of Self-Sexualized Schoolgirls in Young Adult Novels (working title), I’m recapping books 1-8, 13 and 14, which were written by Ziegesar and are based on Ziegesar's experiences at The Nightingale-Bamford School, an Upper East Side all-girls prep school.
Serena van der Woodsen
In book 1, Ziegesar described Serena van der Woodsen, “[a]pproximately age seventeen”, as a “stunning”, “magnetic, [and] delicious” schoolgirl. And as a “tall, eerily beautiful blond girl” with “dark, almost navy blue eyes”, “perfect, pale skin”, a “long, slender waist”, and a “you can’t stop looking at me, can you?” smile supermodels spend years perfecting.” And Ziegesar wrote that, due to her alluring looks, Serena was “a full-on groper magnet”
In response to Serena (S) returning to Manhattan from doing 11th grade at Hanover Academy, a boarding school in New Hampshire, Gossip Girl warned Upper East Side prep school students on gossipgirl.net that if they weren’t careful, among other salacious activities, Serena would have sex in their parents’ beds:
“If we aren’t careful, S is going to win over our teachers, wear that dress we couldn’t fit into, eat the last olive, have sex in our parents’ beds, spill Campari on our rugs, steal our brothers’ and our boyfriends’ hearts [...]”.
Interestingly, in the Vanity Fair piece “‘Gossip Girl Was Me’: Cecily von Ziegesar Talks Manhattan vs. Cobble Hill.” (2020), Ziegesar related that she was, in fact, Gossip Girl. Ziegesar said, “Gossip Girl wasn’t Dan in the books. She was the omniscient narrator. Gossip Girl was me.”
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Note: For the uninitiated, Blair Waldorf was Serena’s best friend. Later in the novel, Blair referred to Serena as a “nasty, slutty bitch”. Mrs. Waldorf is Blair’s mother, and Cyrus would eventually become Mrs. Waldorf’s second husband.
After Serena entered the Waldorfs’ penthouse for a dinner party, which was for the first time after returning from boarding school, Mrs. Waldorf introduced Serena to Cyrus Rose whom proceeded to not air kiss, but kiss Serena on her cheeks, he hugged her “a little too tightly”, and he patted her on the hip.
Mrs. Waldorf smiled, obviously pleased, and wrapped her arm around Serena’s long, slender waist. “Darling, I’d like you to meet my special friend, Cyrus Rose,” she said. “Cyrus, this is Serena.”
“Stunning,” Cyrus Rose boomed. He kissed Serena on both cheeks, and hugged her a little too tightly. “She’s a good hugger, too,” Cyrus added, patting Serena on the hip.
However, due to being “a full-on groper magnet”, Serena didn’t flinch, because she was used to “horny European gropers”. Ziegesar wrote:
Serena giggled, but she didn’t flinch. She’d spent a lot of time in Europe in the past two years, and she was used to being hugged by harmless, horny European gropers who found her completely irresistible. She was a full-on groper magnet.
After Serena was harmlessly groped by Cyrus, Chuck Bass, a prep school student, handed Serena a “tumbler of whiskey”, said, “Welcome Back”, and he ducked down to kiss her cheek, but he missed intentionally “so that his lips landed on her mouth.” However, once again, Serena was unfazed.
“You haven’t changed,” Serena said, accepting the drink. She took a long sip. “So, did you miss me?”
Serena scanned the room with her “dark blue eyes” and discovered: “[...] Nate was standing by the doorway to the hall, and Blair was standing just behind him, her head bowed, fiddling with the buttons on her black cardigan.” (Serena had just unknowingly prevented Nate, a prep school student, and Blair, a Constance Billard School for Girls student, from having sex in Blair’s bedroom while guests arrived at the dinner party.)
After Nate asked Serena, “So, what have you been up to?” She giggled and replied, “If you only knew, Nate. I’ve been so, so bad!”
While observing Serena and Nate’s conversation, Chuck asked Blair, Kati, and Isabel if Serena looked like she had been “thoroughly fucked”, and wondered if Serena had been a Madam for boarding school sex workers. Chuck asked,
“And doesn’t she look fucked? I think she’s been thoroughly fucked. Maybe she had some sort of [teen] prostitution ring going on up there. The Merry Madam of Hanover Academy,” he added [...]
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Most of the Upper East Side prep school students got drunk for the first time in the 8th grade. At one particular party during the 8th grade, “[a]fter drinking six beers”, Nate got “a lot of action”, including from Serena. The party was at Jenny Humphrey’s apartment on 99th and the West End. Rufus Humphrey, Jenny’s father, “kept the beer flowing out of a keg in the bathtub.” Ziegesar wrote:
Buck Naked was Nate’s alter ego, invented at a party in eighth grade, when most of them had gotten drunk for the first time. After drinking six beers, Nate had taken his shirt off [...] and he started a drinking game. Everyone sat in a circle and Nate stood in the middle, holding a Latin textbook and shouting out verbs for them to conjugate. The first person to mess up had to drink and kiss Buck Naked. Of course they all messed up [...] so Buck got a lot of action that night [...]”
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After completing her 10th grade at Constance, approximately 16-year-old Serena spent a hot weekend in August with Nate. The night began with “martinis at the little bar”, and then the teens took a cab to Nate’s Park Avenue townhouse, where they had beer and cigarettes and got wet. Ziegesar wrote:
First they had martinis at the little bar upstairs by the Vanderbilt Avenue entrance to Grand Central. Then they got a cab straight up Park Avenue to Nate’s Eighty-second Street townhouse [...] Serena and Nate had the place to themselves.
They sat out in the garden, drinking beer and smoking cigarettes. Nate was wearing a long-sleeved polo shirt, and the weather was extremely hot, so he took it off.
Serena was hot too, so she climbed into the fountain. She sat on the marble Venus de Milo statue’s knee, splashing herself with water until her dress was soaked through.
After martinis and beer, the uninhibited teens “tore each other’s [wet] clothes off”, and then, oddly in his parents’ bedroom, Nate parted Serena’s Red Sea.
Nate staggered over to the fountain and got in with her, and soon they were tearing the rest of each other’s clothes off.
Nate was worried about the security cameras trained on his parents’ house at all times, front and back, so he led Serena inside and up to his parents’ bedroom.
They both had sex for the first time. It was awkward and painful and exciting and fun, and so sweet they forgot to be embarrassed. It was exactly the way you’d want your first time to be, and they had no regrets.
“You parted my Red Sea!” she howled, wrestling Nate against the pillows.”
After Serena and Nate had a “huge feast of Chinese food and bad white wine”, Nate: “[...] parted her Red Sea once again before the sky grew dark and the stars twinkled in the skylight.” How romantic.
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Back at the dinner party, Serena said, “Shit. I missed you like crazy, Nate. I wish you could’ve seen the stuff I pulled. It was so bad.” Consequently, Nate imagined Serena: “[...] hosting orgies in her dorm room at Hanover Academy and having affairs with older men in hotel rooms in Paris.” Really?
It’s not clear if Serena participated in orgies over the summer or had age-gap sex in Paris, but, in terms of age-gap affairs, Nicholas, a “French college guy who never wore underwear”, chased Serena’s train “in a tiny Fiat all the way from Paris to Milan.”
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Over dinner at the dinner party, Serena shared with Cyrus, of all people, that while she was in the South of France over the summer, she went topless on the beach. Serena asked Cyrus, “How else could I get a decent [teen] tan?”
Later in the novel, Ziegesar elaborated that the beach was in Cannes and that Serena was “drinking Pernod and dancing naked”. Bottemless?
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Ziegesar did not make Serena a “Girls Girl”. Rather, while her boarding school doormates preferred to eat popcorn together in their pajamas while watching SNL, Serena preferred to: “[...] drink peach schnapps and smoke cigars with the boys in the chapel basement.”
However, back in Manhattan, when not indulging in spirits at the Star Lounge in the Tribeca Star Hotel: “Serena and her friends would spend half the night getting dressed together, swilling gin-and-tonics, dancing around in their underwear, trying on crazy outfits.”
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After 17-year-old Serena arrived at the Whitehot Gallery in Chelsea in her “favorite black leather jeans”, she “grabbed a free gin martini before she was approached by one of the “absolutely gorgeous” 26-year-old Remi twin-brothers. Moments later, one of the twins was kissing Serena’s neck while the other, oddly, “hugged her knees”.
Suddenly Serena felt an arm around her waist [à la Cyrus].
“Hello, ma chèrie. Beautiful girl. What is your name?”
Serena didn’t resist when he pulled her into a photograph with him and his brother for the New York Times Sunday Styles section. [Despite their age differences] [o]ne brother stood behind Serena and kissed her neck while the other knelt in front of her and hugged her knees.
The age-gap photograph was titled Serena and was given to the Public Arts League and New York Transit Authority for an “avant-garde public art program” to be displayed on public transportation all over New York City.
After “[t]wo martinis and three rolls of Remi brothers’ film”, Serena took a cab to Constance and arrived late for the “interschool play rehearsal”.
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While having a “Ketel One and tonic. [with] Extra limes” and smoking a Gauloises in the Star Lounge in the Tribeca Star, Serena shared with Blair that she was expelled from boarding school for having a long-term absence due to remaining in France an extra three weeks, where she lived in an “amazing chateau outside of Cannes” and where she fell in love with “two boys, an older brother and a younger one”, however, Serena confessed that she was: “[...] even more in love with their father, but he was married.”
“Blair,” Serena said. “The only reason I got kicked out was because I didn’t show up at the beginning of school. I stayed in France. My parents didn’t even know. I was supposed to fly back at the end of August, but I stayed until the third week in September. I was living in this amazing chateau outside of Cannes, and it was, like, a constant party. I don’t think I slept a whole night the entire time I was there. It was like those parties in that house in The Great Gatsby.”
“There were these two boys, an older brother and a younger one, and I was totally in love with both of them. Actually,” she laughed, “I was even more in love with their father, but he was married.”
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Chuck listed the activities that Serena was (allegedly) involved in while she attended boarding school. For example, of Serena, Chuck said, “You got kicked out of boarding school because you are a perverted slut who made marks on the wall above the bed in your dorm room for every boy you did.”
When Dan asked Serena if what Chuck alleged was true, Serena “fished in her bag for a cigarette” and asked slyly, “Well, what do you think?”
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Lastly, it may be worth noting Serena’s over-the-top residence. Ziegesar wrote:
Home was 994 Fifth Avenue, a ritzy, white-glove building next to the Stanhope Hotel and directly across the street from the Metropolitan Museum of Art. The van der Woodsens owned half of the top floor. Their apartment had fourteen rooms, including five bedrooms with private bathrooms, a maid’s apartment, a ballroom-sized living room, and two seriously cool lounges with wet bars and huge entertainment systems.
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