[The original CW Gossip Girl series was called “Mind-blowingly inappropriate.” by the Parents Television Council, “Very bad for you." by the San Diego Union-Tribune, and “A nasty piece of work.” by the New York Post. However, I would argue that the young adult novel series is inarguably more salacious. I plan to recap books 1-8, 13, and 14, which were written by Cecily von Ziegesar and are based on Ziegesar's experiences at The Nightingale-Bamford School, an Upper East Side all-girls prep school.]
Jenny
As you may recall from book 2 part 1, Jenny is a 14-year-old “lowly ninth-grader” at Constance Billard School for Girls, which is a “small, elite, all-girls school on East Ninety-third Street”, where uniforms are required. And you may recall that Ziegesar wrote that during foreplay with Blair, Nate’s erection “stuck out, tentlike” in his “red-and-white checked boxers”. Interestingly, likewise, Ziegesar wrote that Jenny’s “enormous” “boobs” caused her “pink nightgown” to form a “tentlike triangle”. In terms of Jenny, Ziegesar penned:
She stood in front of the mirror holding her breath and pushing her stomach out as far as it would go. It still didn’t stick out as far as her boobs, which were enormous for a ninth-grader. Her pink nightgown fell in a tentlike triangle from her breasts to her knees [...]
“Freak,” Jenny Humphrey whispered to her reflection.
(Note: Recall that in book 1, Ziegesar referred to Jenny’s “boobs” at least nine times. For instance, in book 1, Ziegesar wrote that Jenny’s “boobs” were: “[...] incredibly huge. At fourteen, she was a 34D.")
Consequently, when Jenny met Nate at “the edge of Sheep Meadow”, Nate, “tanned” with “dark honey-gold” hair, immediately noticed Jenny’s “huge” chest. Ziegesar wrote:
She reached the edge of Sheep Meadow and stepped onto the grass.
Jenny looked up. [Nate] […] the golden boy, standing only thirty feet away, hands on his hips, his green eyes sparkling. His cheeks were flushed pink and his forehead was beaded with sweat. Jenny wanted to taste it.
Nate noticed Jenny’s chest. Man, was it ever huge. He couldn’t let her get away, not without Jeremy and the other guys getting a chance to check her out.
That’s correct. Per Ziegesar, Jenny wanted to taste Nate’s sweat. (LOL) And Nate wanted the other seniors to check out Jenny’s huge chest.
After mingling in Central Park, Nate took Jenny to his bedroom in his Upper East Side (triplex) townhouse, which had red marble floors and famous artists like Renoir, Sargent, and Picasso “on every wall”.
After Nate said, “Let’s go upstairs,” Jenny followed Nate to his bedroom, which had an “antique sleigh bed” and an “ultramodern, ultracool desk with a wafer-thin laptop sitting on it”. Without being asked, Jenny sat “nervously on the edge of the bed”, where she searched Nate’s “emerald green” eyes and shared, “I’m only fourteen”. What was 17-year-old Nate’s response? Ziegesar wrote:
Nate reached up and touched her curly brown hair, combing it ever so gently with his fingers. Then he put his hand down again. “I know,” he said. “It’s okay.”
Although, Ziegesar left it flirtatiously ambiguous, based on forthcoming chapters, readers can safely infer that Nate did not have sex Jenny the first time she sat on his antique bed.
In the Gossip Girl post “EVERYBODY’S DOING IT”, Gossip Girl was asked about her thoughts on “older boys dating young girls”. Gossip Girl opined that “a college senior dating a high school sophomore” is a bit of a problem, that “a high school senior dating a college freshman” is “okay”, but a 12th grader dating a 9th grader is “pushing it”; however, in what most people, I would imagine, would consider to be a counterintuitive and controversial stance, Gossip Girl opined that age-gap affairs “work better” when the “the girl is the younger one”. Ziegesar wrote:
Dear GG,
What do you think about older boys dating younger girls?
—Sneaky
Dear Sneaky,
It definitely depends on the age difference and the circumstances. For instance, if you were a college senior dating a high school sophomore I would say you had a bit of a Woody Allen-Soon Yi Previn problem. If you were a high school senior dating a college freshman, that would be okay. A high school senior dating a high school freshman is pushing it. It seems to work better when the girl is the younger one, mainly because we mature much faster—in all ways.
—GG
Notes:
Ziegesar’s Woody Allen-Soon Yi Previn reference is about Woody Allen’s affair with Soon Yi Previn, which began when Soon Yi was Woody’s teen stepdaughter. For further information about Woody and Soon Yi’s affair and eventual age-gap marriage, reference the Substack piece “The Same Thing Only Different: Nympholepsy in Woody Allen’s Art and Affairs”
In a (somewhat) related note, in the FAMILY MATTERS post, Gossip Girl encouraged what she called “innocent flirting with your stepbrother-to-be”, because it “isn’t sick or illegal”. And she described what some would refer to as incest as “pretty fun and pretty damned convenient”; especially “if you live in the same house!”
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| Woody Allen and Soon Yi Previn |
One reason that readers may infer that Nate and Jenny did not have sex (yet) is that after Jenny met Nate on the steps of The Met, she thought: “Oh my God, [...] He’s about to kiss me.” He didn’t. The arrival of Nate’s friends (temporarily) prevented Jenny from getting what she so desperately desired.
By this point in book 2, readers are up to about ten references to Jenny’s boobs. [I lost count.] Unsurprisingly, the count continues to rise up until the end of book 2. For example, after Jenny joined Nate and his friends on The Great Lawn, her “big boobs’ were spotted by none other than Dan, Jenny’s brother. Of Dan, Ziegesar wrote:
Puffing away, he stared across the grass. A short girl with big boobs and curly brown hair was playing soccer with four boys he recognized only vaguely. It was his sister, Jenny. Since when did she hang out in the park with those boring, preppy, Upper East Side assholes?
Recall from book 1 that Vanessa, another Constance schoolgirl, was in an age-gap relationship with a Brooklyn bartender. Does that make it less surprising that, over hummus and hot chocolate, Vanessa encouragingly referenced Jenny’s “rack”? Ziegesar wrote:
They walked to a café that specialized in Middle Eastern food and ordered hummus and hot chocolate.
“So, Jennifer. With a rack like that, how come you don’t have like, seven boyfriends?” Vanessa said, pointing directly at Jenny’s chest.
Hummus and hot chocolate?! Seven boyfriends?!
Recollect that Dan referenced his sister’s boobs in book 1. For example, Ziegesar wrote in book 1 that even Dan “could not deny” that his sister’s “boobs were really huge.” However, it turns out that Dan referenced his sister’s boobs in book 2 two times! The second time happened at the St. Claire Hotel during Eleanor and Cyrus’ wedding reception, where Ziegesar wrote that Dan recognized his sister’s “enormous cleavage”. Ziegesar wrote:
Dan slipped into a seat at the end of the St. Claire Hotel bar and ordered a double scotch on the rocks. With trembling hands he pulled a Camel out of his coat pocket and lit it.
Dan’s chest convulsed in a sob and he slumped forward, resting his forehead against the edge of his glass. Out of the corner of his eye, he saw a familiar shock of curly brown hair, the enormous cleavage, the tiny figure.
His sister.
And next to her, with his hands all over her enormous cleavage and tiny figure was that rich bastard, Nate.
Once again, Ziegesar left it flirtatiously ambiguous about what happened between Jenny and Nate in Nate’s bedroom; however, readers learned later that they did not kiss on that occasion, because Ziegesar wrote that the first time Jenny and Nate kissed was while they: “were sitting beside the boat pond in Central Park,” where “Nate pulled her toward him. They both kept their eyes open, smiling as they kissed.” (Note: “Jenny had [previously only] kissed two boys during a kissing game at a party once [...]”)
However, later in book 2, Gossip Girl gossiped on the NOBODY DOES IT BETTER post that: “Word has it N and J have been hooking up after school every day. Poor B[lair].” Interestingly, in book 1, Ziegesar wrote that Blair and Nate “had done everything but” have actual sex. Is that what Ziegesar is implying Nate and Jenny did every day after school?
Vanessa
In book 2, readers learned more about Clark, Vanessa’s 22-year-old boyfriend. (Recall that Gossip Girl posted that “a high school senior dating a college freshman” is “okay”. But at 22, Clark would be more like a college senior.) Ziegesar penned that Clark, a bartender at The Five and Dime, a “dimly lit” bar in Williamsburg, had “red sideburns and beautiful gray eyes”. (Note: Per Google, someone with red hair and grey eyes is extremely rare and appears in less than 1% of the entire human population.)
Despite the fact that Vanessa, who dreamed of being a film major at NYU, was still a (prep) schoolgirl who was sitting in a bar, Clark wasn’t shy about openly expressing his age-gap desires. For example, Clark “ran his fingers through Vanessa’s short-cropped black hair” and “blew her a kiss”. Likewise, Vanessa wasn’t shy about openly expressing her desire for an older boyfriend. Ziegesar wrote:
Clark came over and ran his fingers through Vanessa’s short-cropped black hair.
Clark was the bartender at The Five and Dime [...] Clark was twenty-two. He had red sideburns and beautiful gray eyes
[Vanessa] watched Clark’s butt as he bent over to stock the bar fridge with more bottled beer.
“Hey boyfriend,” she yelled at him. “I’m lonely.”
Clark looked over his shoulder and blew her a kiss.
Thank God for Clark, Vanessa thought.
However, because it was “kind of fun to be such a slut”, Vanessa’s age-gap affair with Clark didn’t stop her from flirting with Dan. For example, during the wedding reception at the St. Claire Hotel bar, Vanessa kissed Dan on his “quivering lips”. Ziegesar wrote:
Vanessa picked a ball of lint off her fishnets and flicked it onto the bar floor. She couldn’t believe she was actually flirting with Dan. She hadn’t even broken up with Clark yet! But it was kind of fun to be such a slut.
She leaned forward and kissed Dan on his quivering lips. “Right,” she said, her mouth still full of nuts.
Gossip Girl
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,” which (some) feminists [parents] may find interesting when one considers that Ziegesar slash Gossip Girl encouraged schoolgirls to “break out those credit cards and hit Bendel’s and Barneys for some [...] sexy fishnet tights, [and] little wool skirts”. Not only did Ziegesar write that bulimic Blair vomited her quenelle, but Gossip Girl encouraged: “The way to any girl’s heart is to tell her she looks tiny. Girls kill to be tiny.” And what was Ziegesar slash Gossip Girl’s advice on how to handle “senior stress management”? Materialism, alcoholism, and (teen) sex. Ziegesar/Gossip Girl posted:
It’s time to break out those credit cards and hit Bendel’s and Barneys for some cool new boots, sexy fishnet tights, little wool skirts [...]
Here’s my recipe for senior stress management: Mix one gorgeous boy with a nice new pair of leather boots, a new cashmere sweater, a long night out, and several drinks. Stir in a very late morning and hot chocolate in bed.
Chuck Bass
Lastly, recall that in book 1, Ziegesar wrote that, due to her alluring looks, Serena was “a full-on groper magnet”; thus, after Cyrus kissed Serena on both cheeks, hugged her a little too tightly, and patted Serena on the hip, Ziegesar penned that Serena didn’t flinch, because she was used to “horny European gropers”. And you may recall from book 1 that after Chuck asked Jenny to introduce him to her breasts, he gyrated his crotch against her ass on the dance floor at The Met, and then Chuck took 14-year-old Jenny into the ladies' room, where he “pulled her dress down so he could get at those massive jugs”. Well, Chuck isn’t mentioned much in book 2, but, unsurprisingly, YA readers learned that he’s up to his old ways. For example, on the dance floor at the wedding reception at the St. Clairel, Chuck promptly groped two Constance schoolgirls: Kati Farkas and Isabel Coates. Ziegesar wrote:
Chuck grabbed both Kati and Isabel’s hands and twirled them away, his hands sliding down their backs to their butts within seconds.
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