Note: In addition to “34D” “Slutty Sex Goddess” Jenny, this recap of Gossip Girl book 1 includes “The Horniest Boy” Chuck Bass, "Huge Slut" Claire and Age-Gap Vanessa
Jenny Humphrey
In Gossip Girl (book 1), Cecily von Ziegesar described Jenny Humphrey, a Constance Billard School for Girls 14-year-old 9th grader, as a “curly-haired” “tiny little freshman” whom “preferred to be invisible.” However, Ziegesar wrote that it would have been easier for Jenny to be invisible: “[...] if her boobs weren’t so incredibly huge. At fourteen, she was a 34D."
In addition, Ziegesar elaborated that Jenny’s “huge chest” had “[...] boobs that were ten times too big for her body.” Ziegesar wrote:
Over French fries and hot chocolate in a booth at the 3 Guys Coffee Shop [...] Blair looked Ginny [i.e., Jenny Humphrey] up and down. Their cute little ninth-grade helper with the huge chest. She was a total glutton for punishment [....]
Shockingly, in book 1 alone, Ziegesar referred to Jenny’s “boobs” at least nine times. For example, while shopping at Barneys for the Kiss on the Lips benefit at The Met, Jenny salivated over the beautiful dresses, and, naturally, she wanted to “try them all on”; however, Ziegesar wrote that: “When you’re a 34D, you’re kind of limited.”
While perusing the Barneys’ racks, Jenny considered trying on a $600 “purple velvet empire-waist sheath with beaded straps”, but after she “held the dress up to herself. The bodice would barely cover her nipples.”
Ziegesar wrote that even Dan Humphrey, Jenny’s brother, “could not deny” that his sister’s “boobs were really huge.”
Note: The fact that Dan commented on the size of his younger sister's “boobs” isn’t surprising considering that Gossip Girl shared that Dan was “not that innocent”, because he was “up to some kinky shit back at summer camp in eighth grade.” Kinky shit? In the eighth grade? In addition, Dan had a crush on Serena as well. Hence, he fantasized about sneaking Serena into his father’s library, where they would “take each other’s clothes off and kiss on the leather couch in front of the fire.”
Maureen, a Barneys saleswoman, gave Jenny, despite only being a 9th grader: “all sorts of good advice about support bras and the latest figure enhancing underwear.” Consequently: “Jenny had never been happier.”
Initially, Jenny tried on three dresses, but it was a “disaster”. For example, the first dress got snagged in her bra, the second dress “didn’t even make it over her boobs”, and the third dress “[...] fit, sort of, except it was bright orange”.
Ultimately, Jenny "yanked the orange dress over her head and whipped off her bra, reaching for a black stretch-satin dress [...] Braless, she pulled the dress on over her head and felt it ooze all over her.” Ziegesar wrote that at that moment, Jenny transformed from 14-year-old “little Jenny Humphrey” to “a dangerous, slutty sex goddess”! In addition, Jenny was encouraged to add a pair of “kitten heels, a thong, and some Chanel Vamp lipstick” [Emphasis added]
Note: The Kiss on the Lips benefit was held by the Constance schoolgirls to raise money for the Central Park Peregrine Foundation. Encouraging gift bags were provided by Kate Spade, which contained “glow-in-the-dark condom[s]”.
At the benefit, Blair observed Jenny: “standing behind her, looking like a human Wonderbra”, but after two flutes of champagne, Jenny wished that “her dress wasn’t so tight.” Subsequently, Jenny was approached by Chuck, “the best-looking boy she’d ever seen” whom asked Jenny to introduce him to her breasts.
“Well, hello,” a deep voice said, hovering above her head.
“Jenny looked up. Her eyes settled on Chuck Bass’s aftershave-commercial face and she sucked in her breath. He was the best-looking boy she’d ever seen, and he was looking right at her.
“Aren’t you going to introduce me?” Chuck said, staring at Jenny’s chest.
Despite his rakish reputation, it was Blair’s idea that Chuck approach Jenny. Initially, Chuck was “skeptical. But not anymore. The cleavage on her! It was definitely his lucky night.”
When Nate entered The Met, he observed: “Chuck, who was gyrating his crotch against the ass” of Jenny. Unsurprisingly, Nate noted Jenny’s “insane cleavage” and how Chuck held “little Jenny girl so tight it looked like her boobs might explode.”
As a matter of fact, due to Chuck’s gropings, Jenny had multiple wardrobe malfunctions (i.e., her boobs bounced out of her dress). Ziegesar wrote:
Chuck had his hands full of Jenny Humphrey [...] She was trying to dance as fast as she could, to keep Chuck from groping her, but it was having the opposite effect. Every time she moved her shoulders, her boobs bounced out of her dress and practically hit him in the face.
“Absolutely delighted”, Chuck “put his arms around Jenny’s waist and pulled her close” and guided her into the ladies’ room, where “Jenny opened her mouth and let him thrust his tongue deep into her throat.”
Note: Jenny “had kissed boys before, [while] playing games at parties.”
Next, Chuck: “pulled her dress down so he could get at those massive jugs”. But before Chuck could go any further, Jenny was saved by Serena and Dan.
Chuck Bass
Ziegesar described Chuck Bass, a Riverside Prep student, as “aftershave-commercial handsome” and “the horniest boy” in the friend group.
Recall that Chuck Bass, a Riverside Prep student, whom Ziegesar described as “aftershave-commercial handsome”, missed Serena’s lips intentionally “so that his lips landed on her mouth.” However, Serena was unfazed. Later he called Serena, “[...] a perverted slut who made marks on the wall above the bed in your dorm room for every boy you did.” He opined that Serena looked like she had been “thoroughly fucked”. And he wondered if Serena had been a Madam for boarding school sex workers.
In addition, unsurprisingly, Ziegesar described Chuck as “the horniest boy” in the friend group. So much so that after hiding in the guest room closet, Chuck crawled into bed with Kati Farkas whom was “so drunk she kept throwing up in her sleep”. Shockingly, Kati’s vomit on the sheets didn’t disturb Chuck, because when it came to schoolgirls “[h]e was completely unshakeable”. Ziegesar wrote:
Chuck Bass, the oldest son of Misty and Bartholomew Bass, was handsome, aftershave-commercial handsome. In fact, he’d starred in a British Drakkar Noir commercial, much to his parents’ public dismay and secret pride. Chuck was also the horniest boy in Blair and Nate’s group of friends. Once, at a party in ninth grade, Chuck had hidden in a guest bedroom closet for two hours, waiting to crawl into bed with Kati Farkas, who was so drunk she kept throwing up in her sleep. Chuck didn’t even mind. He just got in bed with her. He was completely unshakeable when it came to girls.
Naturally, due to coming from old-money, Chuck was not canceled for his schoolboy sexual exploits. Ziegesar wrote:
In other circles, Chuck might have been banished as a slimeball of the highest order, but these families had been friends for generations. Chuck was a Bass, and so they were stuck with him.
And no telling when Chuck’s carnal exploits began, because (possibly) since the first grade, he desired to “sleep” with girls, including Serena. Ziegesar wrote:
All four of them looked at Serena, who was still chatting happily with Nate. Chuck saw the girl he’d wanted to sleep with since he could remember wanting to sleep with girls—first grade, maybe?
Lastly, Chuck photographed the bawdy after-school gatherings in his suite, and recall that he kept the photographs on the coffee table. Besides the photographs of the nude prep schoolers in the hot tub, Chuck had a photograph of “Blair wearing only her underwear, jumping up and down on the bed [of the suite] with a magnum of champagne in her hand.”
Claire and the L’Ecole Schoolgirls
Ziegesar described Claire, a student at L’Ecole, an Upper East Side French prep school, as a “huge slut” and the L’Ecole schoolgirls as the “ho’s of the Upper East Side school system”. Why? Well, Claire and the “L’Ecole girls all wear really tight clothes and short skirts and high heels.” And readers can infer that, like Jenny, Claire’s “boobs were really huge,” because, once “Claire laugh[ed] so hard her boobs nearly pop[ped] out of her shirt”. Gossip Girl posted:
There’s usually a group of kids from L’Ecole standing around outside the pizza place, so N [i.e., Nate] will stop and flirt with this one girl who I’ll call Claire, who acts all shy and pretends she doesn’t speak English, but she’s actually really bad at French and a huge slut.
N has this cute little gag where he buys two slices and he always offers Claire one. She holds onto it the whole time they’re talking and finally takes a little weeny bit off the tip of the slice. Then N goes, “I can’t believe you did that, you’re eating my pizza!” and swipes the thing out of her hands and eats the whole thing in like two bites. This makes Claire laugh so hard her boobs nearly pop out of her shirt. The L’Ecole girls all wear really tight clothes and short skirts and high heels. They’re like, the ho’s of the Upper East Side school system.
When one considers salacious Serena and bawdy Blair, Ziegesar’s description of the L’Ecole schoolgirls as the “ho’s of the Upper East Side school system” seems a bit biased.
Vanessa Abrams
Vanessa Abrams, another Constance schoolgirl, initially wanted: “only one thing in life: to go to NYU and major in film.” However, after she went to a bar to see SugarDaddy, her sister’s band, Vanessa wanted Clark, the bartender. [Emphasis added]
Clark, whom Ziegesar described as in his: “[...] twenties, with red hair, long sideburns, and a cute, sly smile,” informed (approximately) 16-year-old Vanessa that he had a secret crush on her, and he prepared Vanessa a Kiss Me before they shared an age-gap kiss.
“Can I tell you a secret?” Clark said. He poured a few different things into a martini shaker and shook it up.
“What?” she said.
“[...] I’ve kind of had a crush on you since I first saw you.”
Vanessa stared at him. Was he joking?
Clark poured the drink out of the martini shaker into a short little glass [...]
“What’s it called?” she said.
“Kiss me,” Clark said, with an absolutely straight face.
Vanessa put the drink down and leaned over the bar [...] She was about to be kissed.
Almost immediately after their first kiss, “She couldn’t wait to kiss him again”. Subsequently, Gossip Girl posted that the age-gap couple was watching rented horror movies at Clark’s apartment in Brooklyn. However, it appears that Vanessa and the bartender did not have sex, because Gossip Girl asked encouragingly: “Will she and that bartender get it on?”
GOSSIP GIRL [Book 1] Recap: “Nasty, Slutty” Serena (Part 1)
GOSSIP GIRL [Book 1] Recap: “Sex Kitten” Blair Waldorf (Part 2)
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