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.

Odell’s "Gwyneth [Paltrow]: The Biography" of a Rebellious and Sexual Student

Per The Hollywood Reporter piece “Gwyneth Paltrow Burns Before Reading” (November 5, 2025), Amy Odell’s Gwyneth: The Biography “[...] debuted at No. 5 on The New York Times best-seller list [...]”. Odell’s well-read biography naturally covers Gwyneth’s career; however, for our purposes, we focused on Gwyneth’s teen years, which was done to compare Gwyneth’s teen adventures to those of celebrities like Paris Hilton.

Odell wrote that as part of her “extensively researched, [and] thoroughly reported biography”, she “interviewed more than 220 people” from Paltrow’s childhood. For example, Rober Nugent Jr. shared with Odell that he and Gwyneth dated during several summers while they participated as child actors in The Williamtown Theater Festival in the Berkshires of Massachusetts. Nugent related that he and Gwyneth shared a mutual attraction that began when he was “nine, ten years old”, which is intriguing since Nugent was “roughly three years older” than Gwyneth. Nugent shared,

“As young kids, if you call it dating, we dated. So she must’ve been attracted to me and obviously vice versa, even though I was only nine, ten years old,” Nugent said.

Odell wrote that the young couple’s "blissful summers” were mostly spent: “[...] wandering the festival grounds and exploring the woods.” One summer when Nugent was 10 or 11, and Gwyneth was 7 or 8, Gwyneth proposed. Gwyneth even procured a ring and a witness for the ceremony. Odell wrote:

“One summer day when she was around ten or eleven, Gwyneth turned to Nugent and said, “Will you marry me?” She made them fake rings and, with Jake as a witness, they held a ceremony.

However, the young marriage ended in August of that summer before Gwyneth returned to Manhattan.

After Gwyneth turned 11, she matriculated at The Spence School, a tony all-girls prep school on the Upper East Side, where she sneaked out of school, in her “hiked up” uniform skirt, to smoke cigarettes and meet up with boys at the Stoop. (The Stoop was attached to the home of The Preppy Killer.) Gwyneth shared that after she enrolled at Spence, she was “immediately drawn” to smoking. Consequently, she smoked a pack a day throughout middle school and high school.

Nancy Jo Sales related in her New York magazine profile “A Star Is Bred - Gwyneth Paltrow” (July 1996), that by the 9th grade, Gwyneth had blossomed into a “state of stunningness” and that to show off her “coltish legs” Gwyneth took to “hemming her school uniform well above her knees”. A former Spence schoolmate of Gwyneth shared with Sales that, although they all wore their uniform skirts short, Gwyneth, “[...] wore her skirt a little too short.” In addition to smoking and meeting boys at the Stoop, Sales wrote that Gwyneth showed off her coltish legs on Madison Avenue: “[...] where she would escape to smoke cigarettes and flirt with passersby.”

Odell related that while in the 10th grade at Spence, Gwyneth entered her “rebellious phase”. Consequently, she would sneak out of her 5th bedroom to go to bars with “the Posse” (i.e., four other on-the-run Spence schoolgirls). Sometimes Gwyneth would leave a note on her pillow: “I snuck out. I’m at Dorrian’s. You can punish me in the morning.” (Dorrian’s is where The Preppy Killer met his victim, 18-year-old Jennifer Levin.)

Sales related another version of the note that Gwyneth left on her pillow: “Dear Mom and Dad, I didn’t run away. I haven’t been kidnapped. I’m out at the clubs. You can punish me in the morning.”

Not only did 15-year-old Gwyneth frequent bars and clubs, Gwyneth would also attend parties in hotel rooms, or she would host a party in her town house while her parents were away.

In addition to entering her rebellious phase, Odell wrote that during the 10th grade, Gwyneth “began discovering her sexuality” as well. Consequently, after approximately 26-year-old Sheryl Berkoff, a make-up artist and then-girlfriend of Keanu Reeves, gave 15-year-old Gwyneth a “blowjob lesson” behind a movie trailer while smoking cigarettes on the set of Gwyneth’s mother’s film.

Of the blowjob lesson, Gwyneth later shared on the “Gwyneth Paltrow: Dangerous and Scintillating” episode of the Literally! With Rob Lowe podcast (07/23/2020), “I’m sure that I implemented it the first chance I got.” Furthermore, Gwyneth revealed during the podcast that 23-year-old Keanu Reeves was her celebrity crush and that it was “so cool” that, although Gwyneth was a 15-year-old “high school kid”, Sheryl treated her like a sexual young woman; thus, Sheryl made Gwyneth feel “so free”. Gwyneth said,

"I met Sheryl when I was 15 or 16. She was doing my mom's makeup on this TV movie [...] and I was, like, immediately obsessed with her. First of all, she was dating Keanu Reeves, who was my celebrity crush. And she was so cool. And she knew that I was sneaking cigarettes, and she would come smoke with me behind the trailer, and she taught me how to give a blow job, and you know, all the classic Sheryl stuff [...] And I was a high school kid [...] It was less about remembering the technique — although I'm sure that I implemented it the first chance I got. It was so cool to have someone treat me like an adult and see me as, like, a young woman and someone who is sexual. She just made me feel so free."

Rhetorical question: Did Gwyneth ask Sheryl to teach her how to give a blow job, or was the lesson unsolicited? If Keanu Reeves had given Gwyneth the “blowjob lesson”, would Vanity Fair, People, and Newsweek write about the lesson so lovingly?

Gwyneth Paltrow | Hook (1991)

Not only was Gwyneth sexual, but she also possessed a “bawdy sensibility” as well. For example, during the 10th grade, Gwyneth drew an erect penis on a cubicle in Spence’s library. After Gwyneth was confronted by the librarian, Gwyneth replied, “Come on, where’s your sense of humor?” Odell wrote that: “Gwyneth became annoyed when she had to clean it up.”

Reportedly, during her teen years, “Gwyneth dated a lot [...] and talked openly about sex.” Unsurprisingly, Gwyneth dated an older guy as well. For example, Odell wrote that 15-year-old Gwyneth “dated her cousin’s college friend”.

Odell wrote that Gwyneth was described as a “tall, beautiful, thin girl - [with] a lot of arms and legs”, a “pretty blond nepo-baby”, and “ever the extrovert”. Sales related that Gwyneth was “six feet tall with blonde hair down to her waist” and that Gwyneth’s dates included “other people’s boyfriends”. Odell and Sales wrote that Gwyneth confessed, “I kissed somebody’s boyfriend when I was 15.”

Odell wrote that, inexplicably, Gwyneth’s father gifted her “a pair of lace underwear” and that after Gwyneth made reservations at Elio’s, an Italian restaurant on the Upper East Side, patrons assumed that Gwyneth and her father were dating. Odell wrote that Gwyneth’s father said, “The women were staring daggers at me at the tables, and the guys were going, ‘Way to go.’”

Interestingly, for her senior project, Gwyneth recorded a song with Donald Fagen, the lead singer of the band Steely Dan. Arguably, Steely Dan’s most popular song is "Hey Nineteen", which is about a man who rejects the sexual advances of a teen groupie.

Per Odell, at the end of the 1990 season of The Williamtown Theater Festival, 17-year-old Gwyneth attended “an end-of-season party at a bar” with Christine Lemme and Christine’s summer fling, who was in his twenties, but that didn’t stop Gwyneth from groping him (i.e., SA). Subsequently, Christine’s fling informed Christine, “Gwyneth just felt me up!”

As part of a multi-million dollar marketing campaign, in January of 1991, the fashion brand Esprit sent out postcards to young customers with the question: “If you could change the world, what would you do?” Odell related that: “Gwyneth was on the audition circuit, and she was one of the pretty people whose photo ended up on the casting board [...]”

And what was 18-year-old Gwyneth’s reply to Esprit’s question about how she would change the world? Gwyneth replied: “i would distribute condoms in every high school in america.” Odell wrote:

The text ran alongside a black-and-white image of Gwyneth in her own jeans, white T-shirt, and cardigan. She looks musingly off to the side, her hair cascading undone over her shoulders

Over twenty years later, Esprit, ignoring the fact that Gwyneth's initial response was a consequence of her sexual nature, repurposed her response in a 2019 HIV and AIDS prevention campaign.

Gwyneth Paltrow | Flesh and Bone (1993)

And due to a “ease about her” and the fact that she was “Hollywood royalty”, Gwyneth was cast as Ginnie in Flesh and Bone (1993). Per Odell, Risa Bramom Garcia, the casting director, opined that Gwyneth possessed, “[...] a combination of earthiness and depth and intelligence, which was really rare for an actor and especially a nineteen-year-old.” However, the role required nudity, which wasn’t a problem for 19-year-old Gwyneth. Per Odell, Gwyneth didn’t “flinch” when she was informed about the nude scene, because Gwyneth said that she: “[...] would do what[ever] was necessary to play the role effectively.” Odell wrote that Gwyneth’s nude scene was cut from the film, but that isn’t true. Consequently, Gwyneth’s topless scene has been posted on a variety of porn websites that are dedicated to celebrity nudes.

It turns out that Gwyneth's teen years were, unsurprisingly, very similar to Paris Hilton’s. For example, Paris shared in Paris: The Memoir that in the sixth grade at The Buckley School, a prestigious private school in Los Angeles, the tenth-grade boys invited her to sneak off campus. “Sure!” Consequently, like Gwyneth, Paris rolled up her prep schoolgirl skirt “and styled it short.” Reminiscing on the day, she wrote, “I just liked the attention.” And it was at The Buckley School where, during a sixth grade game of Spin the Bottle, Paris had first kiss. (In addition to wearing her sixth grade prep school skirt short, by 8th grade, 14-year-old Paris “found ways to shorten” her Catholic schoolgirl plaid skirt as well.)

Per Paris, since she was “frequently grounded”, she began sneaking out of the house in the 8th grade. Paris would climb out of her bedroom window, “slid down the drainpipe”, and she “maneuvered down to the ground”. Paris was determined “to wear makeup, go on real dates, or hang”. After Paris turned 15, she moved to Manhattan with her parents and siblings into a 2,500 square-foot condo in the Waldorf, but that didn't stop Paris from sneaking out.

Paris’ source for nightlife entertainment was Time Out New York, which she used for: “[...] scoping out the best parties and music and DJs”. Paris would sleep “most of the day” and “[a]fter everyone went to bed” she “headed out”. Paris would “dance and go wild until the morning”, then she “slipped past the doorman”, “took a shower, and fell into bed as everyone else got up to get ready for school.” Sometimes Paris: “[...] crashed at a friend’s house, slept all day, and went back out the next night.” Lastly, Paris shared that after she turned 16, with the help of the Wonderbra, she became a woman. Paris wrote:

“I looked in the mirror, and there was a woman looking back at me. It was helpful that Wonderbra was having a moment.”

Lastly, Odell wrote that Gwyneth and Mr. James Dawson, Gwyneth’s 9th-grade biology teacher, had “a unique connection”; however, it’s unclear if Gwyneth and Mr. Dawson had a student-teacher affair like Paris had with Mr. Abercrombie, whom she described as “handsome” with “tousled hair” and “penetrating eyes”. Their affair was their secret. A secret Paris wrote that was a “[...] secret like candy under my pillow.”

From the NY Times to Netflix: Schoolgirl Sleepover Sex Stories (Part 6) | TikTok Desires, Peeping Parents, and OnlyFans Clickbait

The TikTok "Still No Head" Trend

Of course, not all schoolgirl sleepovers involve sexual activity; however, some schoolgirls don’t understand why there wasn’t any sexual activity. For example, on TikTok, some teens poetically expressed their bewilderment and dismay over not being the recipients of head (i.e., oral sex) during sleepovers. 

For example, one teen TikToker posted that she and her friend “Slept in the same bed” during “So many sleepovers\And still no head”. Another teen related that she and her friend “slept in the same bed 100\times and still got no head”. One schoolgirl even shared that her friend had “seen my boobs” and that they had “showered tg (i.e., together)\ [and] cuddled”, “yet still no head”. And not to be outdone, another teen shared that she and her friend, not only “showered tg”, but that they had “seen every inch of each others [sic] body’s [sic]”, “and still no head”. But those missed opportunities may have been for their benefit.

Recall that 13-year-old Victoria related to Nancy Jo Sales in American Girls: Social Media and the Secret Lives of Teenagers that some moms at a bat mitzvah opined that boy-girl sleepovers were “so cute”. Sophia said to Sales that some parents allow boy-girl sleepovers because “it’s being ‘feminist”’, and Sophia said that the parents allow salacious sleepovers, because they want to be considered “cool” by their daughters. And Savannah, who ruled her Brooklyn, NY middle school, had a “famous dad” whom let Savannah’s boyfriend “stay over at her house all night sometimes”. Savannah told Sales that her parents didn’t want to “repress” or “control her sexuality”. Consequently, Savannah’s classmates considered her and her parents to be “cool”.

However, the desire to achieve cool status may not be the only reason a parent will allow his or her (pre) teen daughter to have a sleepover. Take Rich Cohen’s post on AirMail: “Always Be Suspicious of the “Cool Mom”: A sex scandal involving teens and a mother engulfs upscale Greenwich, Connecticut” (February 26, 2022) 

In the post, Cohen wrote about Hadley Palmer, whom pled guilty to three counts of voyeurism and one count of risk of injury to a minor. Per Cohen, Hadley: “live[d] in one of the swankest houses in Belle Haven, [in] one of the toniest sections of Greenwich, Connecticut, [and in] one of the richest towns in America”. And in that swanky  Connecticut house, Hadley, an apparent voyeur, encouraged teen sex. Cohen wrote:

Beware the cool mom. She says she’d prefer you and your friends not drink, but, if you must, she’d rather you do it in the house, where you’ll at least be safe, which, I promise, you won’t be. She’s against drugs, but will not come down hard on you for it, as long as you keep it at home and let her have a toke, just to make sure it’s on the up-and-up. She’s against pre-marital sex, but says, if you must, because of urges, please not in the car, nor in some dirty motel, but here, in the guest room at the big house by the shore—no, not that room, nor that one, nor that one, nor that one (her house is huge) but in the one at the end of the hall by the maid’s quarters and laundry.

If you don’t believe me, check out the legal papers recently filed in the State Superior Court in Stamford, Connecticut, where 53-year-old Hadley Palmer of Greenwich, after striking a deal with prosecutors, pleaded guilty to three counts of voyeurism and one count of risk of injury to a minor.

Relatedly, Angela Andaloro posted on People “11-Year-Old Calls Mom from a Sleepover After Discovering a Camera in Her Friend's Bedroom” (March 12, 2025) In the piece, Andaloro related that, during a sleepover, an 11-year-old girl noticed that there were cameras in her friend’s room. The cameras were supposed to be for security purposes but turned off; however, there were lights on the cameras that indicated that the cameras were recording. And after the 11-year-old put a shirt over a camera, the mother of the sleepover host “removed the shirt, didn’t say anything and left". Andaloro related:

[...] the mom explains her 11-year-old daughter went to a sleepover with another friend. When the pair got to the third girl's home, they discovered "there were 'security cameras' in her friends [sic] room," she writes.

"When asked about it, she was told by the parents that they were for security purposes and that they were 'turned off,' " the mom explains, noting her daughter could tell that wasn't the case. A light on the cameras indicated they were turned on. Uncomfortable, the girls put a shirt over the camera.

"The parent came into the room, removed the shirt, didn’t say anything and left," [...]

Knowing that (some) adults are aware of the sexual activity that takes place at (some) schoolgirl sleepovers, (some) OnlyFans content creators use the allure of schoolgirl sleepover sex to gain subscribers. 

The subtitle for Rebecca Jennings’ Vulture\New York Magazine piece “They Make Millions Acting Like Sexy Babies”. (Aug. 21, 2025) is: “How the Bop House, an OnlyFans influencer group, conjures a fantasy of young girls having a horny sleepover.”  In the piece, Jennings wrote that the Bop House members conjured “a fantasy of young girls having a horny sleepover”. The conjuring was done by wearing braces, girlish rompers, midriff-baring cartoon pajamas, onesie pajamas, and Pokémon slippers. And for emphasis, the OnlyFans content creators used cartoon sound effects in their TikTok videos, which were used to drive viewers to their OnlyFans accounts, where they can make thousands per month. Jennings wrote:

Several members even wear braces, which they claim are orthodontic necessities. In loosely choreographed TikTok dances, they wear matching snug leotards, girlish rompers, curve-hugging Skims maxi dresses, and midriff-baring cartoon pajamas [...] The audio in many of their videos is essentially cartoon sound effects, and much of what happens in them emphasizes their youth, from wearing Pokémon slippers and jumping on couches to feeding each other lollipops [...] Paired with onesie pajamas, e-girl makeup on an already young-looking face [...]

Julia Filippo, a 23-year-old Bop House member, shared with Jennings that she “blew up” on OnlyFans, because “men love” her innocent appearance. 

“That’s how I blew up, because men loved how innocent I looked,” says [Julia] Filippo.

In addition, Jennings related that in a viral online video, Camilla, another 23-year-old Bop House member, asked Julia how much money she made in her first week on OnlyFans. After Julia shared that she made a whopping $54,000, Camilla opined that it was, “[...] ’cause she looks 12.” 

Lastly, yet intriguingly, Jennings opined that we would be naïve to assume that Julia, Camilla, and the other Bop House members aren’t aware of the power that appearing younger has given them. Jennings wrote: 

“Though none of the Bop House members I spoke to admitted to deliberately making themselves appear younger, it would be naïve to assume they don’t know the power it has given them.” 

From the NY TIMES to Netflix: Schoolgirl Sleepover Sex Stories (Part 1):
Becca Moore, Miley Cyrus, Jessica Simpson and Julia Fox

From the NY TIMES to Netflix: Schoolgirl Sleepover Sex Stories (Part 2):
Lola Kirke, Chelsea Handler, and Lena Dunham

From the NY TIMES to Netflix: Schoolgirl Sleepover Sex Stories (Part 3): 

Restless Virgins | Zoe, Isabel, Annie, and Whitney

From the NY TIMES to Netflix: Schoolgirl Sleepover Sex Stories (Part 4): 

Camp Cabins

From the NY TIMES to Netflix: Schoolgirl Sleepover Sex Stories (Part 5):
Sleepover Sexting and (Virtual) Sleepover Sex

From the NY TIMES to Netflix: Schoolgirl Sleepover Sex Stories (Part 5)

 

In the film Miller’s Girl (2024) [Lionsgate], during a sleepover, Cairo (Jenna Ortega) and Winnie decided to sext Mr. Fillmore - their high school’s physics teacher. In the sext, the schoolgirls were engaged in girl-on-girl kissing and “measuring the depths of our sexuality”, which, per Winnie, is what all schoolgirls do when they’re alone at night.

"Miller’s Girl" (2024) | Cairo and Winnie Sext Mr. Fillmore

Cairo said to Winnie, “You should tell him [via sext] you’re with me. And that we’re doing what all girls do when they’re alone at night.”

Mr. Fillmore texted: And what might that be?

Cairo said to Winnie, “[Tell him] [w]e are measuring the depths of our sexuality within the safe confines of our friendship.”

Consequently, in addition to sex, sexting can occur during schoolgirls’ sleepovers as well. In American Girls: Social Media and the Secret Lives of Teenagers (Knopf, 2016), Nancy Jo Sales wrote about a number of instances of schoolgirl sexting during sleepovers. 

As an example of how much, in general, teen sexting occurs, Sales referenced Kassondra Cloos and Julie Turkewitz’s New York Times piece “Hundreds of Nude Photos Jolt Colorado School” (Nov. 6, 2015). The article is about a “large sexting ring” at Colorado’s Cañon City High School, which had over 300 nude pictures of over 100 different students that included not only Cañon City High students but “eighth graders from the middle school” as well.

Cloos and Turkewitz wrote that George Welsh, the superintendent of the Cañon City school system, said that: “a significant percentage of the student body at Cañon City High School had participated, with boys and girls involved in seemingly equal numbers.”

And Cloos and Turkewitz related that, in general, “sexting among children is a rampant problem”, which is very true. Take the ABC News report “Police Bust Virginia Sexting Ring Involving More Than 100 Teens: Explicit photos of underage girls posted to Instagram account.” (April 5, 2014) ABC News reported on a “teenage "sexting" scandal in [Louisa County] Virginia, involving more than 100 teens and more than 1,000 photos of underage girls posted to a[n] [IG] social media account.”

(Pre) teen sexting is so rampant that Cloos and Turkewitz wrote that Amy Adele Hasinoff, a University of Colorado Denver professor and author of Sexting Panic: Rethinking Criminalization, Privacy, and Consent (2015, University of Illinois Press), opined that adults should stop “demanding that students abstain from sending risqué images” but that schoolgirls need “guidance in “safer sexting” with trusted partners.”

Let’s look at some specific examples from schoolgirl sleepover sex and sexting from American Girls:

Sales described Riley, a 13-year-old middle-school student in Montclair, New Jersey, as “a green-eyed girl with dark blond hair”. (“Riley’s parents were writers.” #relatable) As Riley exited her middle school, she received another request, via Snapchat, for nudes. Since Riley had allegedly performed oral sex on Danny, whom she “had been dating for about six months”, Riley’s classmates assumed that she would be more open to sending nudes.

Riley and Danny had “hooked up for the first time” at “a house where the parents weren’t there; such parties took place in the afternoons when parents were at work”. In addition to “weed and vodka”, there was “making out, blowjobs, [and] handjobs”.

Subsequently, Riley hooked up with Danny in his bed during sleepovers. Danny’s parents even provided the middle-school couple with breakfast in bed! Riley said,

“We went over to each other’s houses. I had sleepovers at Danny’s house. His parents made up breakfast and brought it up to his room.”

Victoria, a 13-years-old “brown-haired and freckled faced” schoolgirl, added that she, “[…] heard some moms at a bat mitzvah talking about their kids having a boy-girl sleepover.” Victoria said that the moms thought heterosexual sleepovers were “so cute”. And Sophia, “tall, with straight black hair”, said that parents do it because “it’s being ‘feminist”’, and the parents want to be considered “cool” by their daughters.

Unlike the dad in the New York Times THE ETHICIST piece, who let his mid-teen daughter have girl-on-girl sex during sleepovers with her best friend, because there are no penises involved, Riley, Victoria, and Sophia said that they: “heard of parents who allowed their daughters to have sleepovers with a boyfriend.”

Savannah, who wore “short shorts and halter tops that showed “side boob”, ruled her Brooklyn, NY middle school. Savannah had a “famous dad” who was “someone in the news”, she had a nanny, and an additional house in the Hamptons with a pool. Savannah’s parents let her boyfriend “stay over at her house all night sometime”. Savannah shared with Sales that her parents didn’t want to “repress” or “control her sexuality”. Consequently, Savannah’s classmates considered her and her parents to be “cool”.

(Of course, some parents don’t condone sex during sleepovers. After a parent learned that, for clout, content from salacious sleepovers gets posted on social media, the parent asked, “And lying in bed together and putting their hands in each other’s pants. They’re sixteen years old and they’re grabbing each other’s crotches! Where are these parents? What room and what bed are they lying in?”)

Michelle, a 17-year-old blond from Boca Raton, said that she got her first “[…] dick pics in the sixth grade.” Michelle’s mother: “had her own business and her father was an engineer.” Michelle was distraught, because after she had sex with Kyle, whom she described as “really sexy”, Michelle found out that Kyle, “[…] had a girlfriend named Morgan.” The news was extra upsetting, because Kyle and Michelle were “hooking up” during a sleepover at Michelle’s house the night before she found out about Morgan. Morgan shared with Sales,

“Like that weekend Billie sent me the picture of him [Kyle] and his girlfriend [Morgan], he had stayed over at my house the night before. So he was hooking up with me and then posting ‘couples’ pictures with her. So he’s been hooking up with me and her […]”

Consequently, during school, Michelle showed Morgan Kyle’s “dick pics” that were saved in her phone.

Virtual Schoolgirl Sleepover Sex

Lastly, sometimes (pre) teens are involved in sexual activity during what I refer to as “virtual sleepovers”. Recall that Lola Kirke and Chelsea Handler were involved in teen group masturbation sessions. Connectedly, Kim Goldman, the director of the Santa Clarita Valley Youth Project, told Sales that at one of Santa Clarita junior high schools, “[…] kids were having an online [masturbation] orgy. They all signed in to a video chat room.”

A 25-year-old New Yorker told Sales that when he was in the 7th grade, he participated in orgiastic webcam shows on MSN Messenger, and that the nude shows were so exciting that middle-schoolers were having orgasms. Sales wrote:

When webcams came out, kids started putting on shows for each other and participating in mutual masturbation, live. “We did webcam shows on MSN,” says a young man in New York, age twenty-five, referring to the now discontinued instant-messaging service MSN Messenger, which appeared in 1999. “It started in seventh grade. You’d show your weiner in the webcam. We played strip poker. It was always about playing games. But then it would get too exciting and somebody would bust a nut.”

And Julie, a 13-year-old from Boca Raton, shared with Sales that a visiting schoolgirl wanted to, “[…] video chat with some boys on FaceTime - naked. She came out of the closet [in my bedroom] naked, ready to answer the call […] She wanted to be naked in front of the boys.”

In the end, what may be just as interesting as these schoolgirl sleepover sex stories is the answer to the question: Why were these salacious stories shared? We learned that they were shared for attention (e.g., likes, followers, comments, “social clout”, etc.), and money (e.g., YouTube subscribers, Netflix streams, memoir\(non-fiction) book sales, etc.). And per Jones and Miller, as they opined in their Bestseller, another consequence of these revealing stories is that they efficiently exemplify the “myth of innocence”.

From the NY TIMES to Netflix: Schoolgirl Sleepover Sex Stories (Part 1): Becca Moore, Miley Cyrus, Jessica Simpson and Julia Fox

From the NY TIMES to Netflix: Schoolgirl Sleepover Sex Stories (Part 2): Lola Kirke, Chelsea Handler, and Lena Dunham

From the NY TIMES to Netflix: Schoolgirl Sleepover Sex Stories (Part 3): Restless Virgins | Zoe, Isabel, Annie, and Whitney

From the NY TIMES to Netflix: Schoolgirl Sleepover Sex Stories (Part 4): Camp Cabins