Jill Kargman’s BITTERSWEET SIXTEEN'S Salacious Prep Schoolers

Here’s the overview posted on Barnes & Noble for Carrie Karasyov and Jill Kargman’s Bittersweet Sixteen (HarperCollins, 2006):

Co-written by bestselling authors Carrie Karasyov and Jill Kargman, star of the Bravo series Odd Mom Out, Bittersweet Sixteen is a story of friendship, drama, and the hazards of turning sixteen.

A brand-new wardrobe from Saks, a private jet, and a red-carpet guest list: just your average Sweet Sixteen party.

At least it is for the teens who attend Tate, the posh all-girls high school in Manhattan. But Laura Finnegan—thrift store junkie and scholarship student at Tate—isn't like everyone else. And when her best friends Whitney and Sophie begin obsessing over their birthday bashes, tempers start to flare, Prada bags go flying, and guys are tossed around in vicious tug-of-war battles. Whose Sweet Sixteen will reign supreme?

It’s worth noting that, in addition to being a (former) Bravolebrity, Kargman, per the Wall Street Journal piece “Bullets and 'F-Bombs'” (October 11, 2011), is an Upper East Sider* who, like Gwyneth Paltrow, went to The Spence School, a tony all-girls prep school in Manhattan, which, per Harper Collins, is where Kargman met Karasyov; thus, Kargman and Karasyov may be the ideal co-authors for a novel like Bittersweet Sixteen. 

In preparation for a new book, From Gossip Girl to Pretty Little Liars: A Study of Age Gap Relationships in YA Novels, I’ve read a number of YA novels that are set in Manhattan prep schools, but the level of materialism in those novels ceases to amaze me. For example, here’s Bittersweet Sixteen’s opening paragraph:

There’s one thing you have to know. In the world of private schools, penthouses on Park Avenue, chauffeur-driven Bentleys, and $100-a-plate family dinners at Le Cirque, one thing reigns supreme as the pinnacle of a tenth-grade girl’s social calendar in New York: the almighty Sweet Sixteen birthday extravaganza. [Emphasis added]

The Plaza

As for the Sweet Sixteen extravaganzas, Sophie’s was held at The Plaza, where “Male models dressed as Tarzans swung from leafy vines [...] Thong-clad “tribal” waiters passed shish kebabs from flaming serving trays and little rawhide tents were scattered around the room”. 

Interestingly, Laura narrated that “most teens” used the little rawhide tents for “heavy petting sessions”. (Oxford Languages defined heav·y pet·ting (noun) as “erotic contact between two people involving stimulation of the genitals but stopping short of intercourse”.) The (teen) heavy petting that took place in the tents at Whitney’s Sweet Sixteen brings me to the next common theme slash motif that I’ve noted in YA novels that are set in Manhattan prep schools, which is self-sexualized (i.e., provocative) schoolgirls. 

For example, in Bittersweet Sixteen, Sophie was described as blond with “white teeth and very plump lips”. Like Gwyneth Paltrow and her classmates at Spence, Sophie tailored her schoolgirl uniform skirt “way above the knees”, and she pulled her “white oxford ever so tight around her suspiciously ample boobs”. (Was Laura implying by narrating “suspiciously ample” that Sophie may have had a (teen) boob job?)

Sophie didn’t understand why Tate’s headmistress didn’t approve of how tightly she wore her uniform shirt, which Sophie did to strategically accentuate her “boobs”.

“I can tell. The headmistress gave me daggers when she saw how tight my shirt was. Do they, like, want us to forget that we have boobs? Why don’t they just suit us up in nuns’ outfits and strap them down?” said Sophie.”

Even off campus, Sophie accentuated her boobs. For example, one day “buxom” Sophie wore a “too-tight V-neck black [Dolce & Gabbana] sweater.” In general, whether on or off campus, Sophie wore her clothes “short, tight, revealing, and [with] logos.” Consequently, Sophie was considered “a blond stick with knockers.” And despite Sophie being a mere 15-years-old, “She was sexy.” Consequently, “guys were going to lap [her] up with a spoon.” Whatever that sexual innuendo means.

Marquee

Like Gywneth, Sophie, and some of her classmates sneaked out of the house. Sometimes they sneaked out to meet up with schoolboys (e.g., at the San Gennaro festival), and sometimes they went to clubs too (e.g., Marquee). 

In reference to sneaking out of the house, Sophie exclaimed that parents, in general, are clueless, but that her parents, in particular, didn’t even realize that she was not a virgin. 

“Parents are clueless!” Sophie laughed. “Mine still think I’m a virgin!”

Sophie considered it a badge of honor that she wasn’t a virgin. So much so that she referred to Whitney as a “Waspy repressed virgin”. However, Karasyov and Kargman did not disclose exactly at what age Sophie began to have sex and to whom she lost her virginity. 

Another common theme slash motif that I’ve noted in YA novels that are set in Manhattan prep schools is age-gap relationships. Specifically, student-teacher relationships. For example, in Bittersweet Sixteen, Laura narrated that Sophie flirted with Mr. Everwood, whom Laura described as a “hottie teacher”. And Laura shared that there was a rumor on Tate’s campus that Mr. Everwood “had banged a senior”. Laura narrated:

Then, in the science lab, Whit’s eyebrow arched ever so slightly as Sophie giggled flirtatiously with Mr. Everwood, the hottie teacher (who, rumor had it, had banged a senior the year before). 

Note that Karasyov and Kargman strategically made the schoolgirl whom Mr. Everwood “banged” a senior (i.e., over 17-years-old), and I find it intriguing that Karasyov and Kargman used banged to describe the way the hottie teacher had sex with his student. 

(In addition to the rumor about the hottie teacher, there was a “whole scandal with the previous piano teacher.”)

Not only did Sophie flirt with her hot teacher, but she flirted with the “guy in the deli” and “the guy who plays the piano in chorus”, which was no big deal, because it was “Sophie’s nature to flirt. Laura said,

“I think it’s just in Sophie’s nature to flirt. I mean, come on, she flirts with the guy in the deli, she flirts with the guy who plays the piano in chorus, she’s just that way [...]” 

(Note that Sophie’s father was “like thirty years” older than her mother. )

Sophie had a “mini-soiree” at her UES residence, where Sophie and Kaitlin wore “[...] ubershort cutoff jean skirts. If they bent over, you could literally see their thong.” And after “several wine coolers” at Sophie’s, the prep schoolers played Spin the Bottle slash Three Minutes in Heaven, which reminded me of Julia Fox.

In Down the Drain (Simon & Schuster, 2023), Julia Fox’s memoir, she shared that when she was 11-years-old, she started 6th grade in the fall of 2001 at East Side Middle School on the UES, where, like Gywneth, she smoked a “cigarette here and there”, and she started “wearing dark lipstick to class”. (p. 28-29)

Ella, Julia’s straight-A student classmate, introduced Julia to marijuana. Julia wrote that before her first hit in Ella’s bedroom, her heart pounded through her Playboy tank top. [Emphasis added] Ella taught Julia how to “roll joints with a filter, ‘like the French’”. And Julia and Ella kissed each other “like the French”. Ella, who had “beautiful thick auburn hair and big green eyes”, insisted that their pre-teen girl-on-girl kissing was “practice for the real deal”, but Julia sensed that Ella liked kissing girls. Julia wrote:

“We play[ed] games like spin the bottle and seven minutes in heaven [i.e., in the closet kissing], and then we pretend[ed] like it didn’t happen.” 

Back to Sophie, ever the model friend, she volunteered to find Laura “a real man”, which was doable for the well-connected Sophie who had the contact information for a number of celebrity men. Although Sophie had access to Matt Damon, whom was 36 when Bittersweet Sixteen was published, Sophie settled on hooking Laura up with Elijah Wood, whom was 25 when Bittersweet Sixteen was published. 

“Yeah, as if,” I [i.e., Laura] said, dejected.

“You never know,” said Sophie. “It will be my mission to hook you up.”

The Pierre

In terms of over-the-top materialism, Whitney’s Sweet Sixteen was held in the ballroom of The Pierre, where “Peter Duchin’s famed orchestra” played, “David Copperfield performed”, “Oscar de la Renta toasted Brooke Astor”, and the “New York Times’ Bill Cunningham snapped away”.

Whitney, who “sampled her first potato galette with caviar at age seven”, was described as “pretty much perfect” with “buttery blond” hair, “blue-eyes”, and with “Waspy facial architecture”. The summer before her 10th grade at Tate, Whitney, in addition to beachside clambakes and tennis lessons, indulged in “heavy petting [i.e., erotic contact] with the Greystone Country Club lifeguard.” The lifeguard was recruited by “Abercrombie’s scouts”, he was “ripped and stuff” and, unsurprisingly, he was “older”. 

The exact age of Whitney’s lifeguard wasn’t shared with readers, but it’s safe to assume that he was approximately 20-years-old, because, per the Us Weekly piece “Celebs Who Were Abercrombie & Fitch Models Before They Were Famous” (April 22, 2022), Channing Tatum was 21 when he modeled for Abercrombie in 2001. 

As for Laura, she admitted that she had participated in “minor hookups and stuff”. For example, she “hung out” with a “guy” (i.e., not a boy) at camp, and they “kissed twice”. (It’s unclear if the kissing is considered part of the minor hookup or the stuff.) However, due to her “un-Barbie looks (brown hair, brown eyes, kinda pale, and oh yeah, small boobs), Laura narrated that she was “hardly schoolboy drool material.” Thereby, Laura implied that if she were a blond with large boobs, like Sophia, she would have participated in major hookups and stuff. 

Laura was the most studious in her friend group. She even took art class very seriously, where at Tate the art teacher provided the schoolgirls with “a male ‘model’ [...] posing buck naked” to draw at their easels. 

Laura shared that she participated in “minor hookups and stuff”, but after Sophie’s exclamation, Laura related that Whitney participated in a lot of hookups, and that Kaitlin, with her strawberry blond hair, Chanel quilted tote, and cashmere sweater-coat, was considered “the sluttiest” of the gang. However, although Kaitlin considered “giving it up to Max”,  she, Whitney, and Laura were still virgins.

I looked at Whitney, who appeared floored. Even with all her hookups, she had not gone there. I mean, Kaitlin, the sluttiest of our gang, had just started talking about maybe giving it up to Max [...]

But if Laura engaged in hookups, although minor, they were plural, and if Whitney participated in a lot of hookups, what in the world did Kaitlin do to be considered the sluttiest of the gang?

Lastly, make no mistake, Karasyov and Kargman are not misogynistic, because some of the schoolboys in Bittersweet Sixteen were provocative as well. For example, Bobby, with his “blond hair and blue eyes”, was referred to as a “male slut” who had “laid more pipe than Con Edison. Total player.” Consequently, Whitney opined, “Bobby is a total babe.” And despite being a prep schooler, Bobby kept a flask for doing shots. 

*Based on the New York Times piece “Mamdani’s Success Spotlights a Deepening Rupture Among U.S. Jews”, due to the election of Mayor Mamdani, Kargman may have left Manhattan.