Braless Serena and Sex Machine Blair | GOSSIP GIRL [Book 2] Recap (Part 1)

Gossip Girl: You Know You Love Me (Book 2): Serena and Blair

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. 

Serena van der Woodsen

If you’re a fan of the television series, you may be surprised to learn that Serena, a senior at Constance Billard School for Girls, had a small role in Gossip Girl: You Know You Love Me (Book 2). For example, in book 2, Ziegesar further described Serena as having “dark blue eyes”, that Serena’s “pale [“shimmering”] blond hair” had a “golden brilliance”, that Serena’s “pale skin had a pearly sheen from years of using La Mer skin cream”, that Serena “smelled like Chanel No. 5,” and that Serena was prone to wear a “sweater with nothing underneath it.” Consequently, “Serena was like, the coolest senior in New York”.

In addition, readers were reminded about Serena’s wealth and privilege. Ziegesar wrote:

Serena lived with her well-heeled parents […] with a view of the Metropolitan Museum of Art and Central Park. She had a maid and a cook who she could ask to bake her a cake or make her a cappuccino any time she wanted.

Lastly, as for book 2 and Serena, readers were reminded that Serena and Blair’s friendship turned “sour” after Blair learned that Nate, Blair’s boyfriend, had sex, twice in one night, with Serena “nearly two years ago”, which was when Nate and Serena were 16. 

Blair Cornelia Waldorf 

Book 2 began with 16-year-old Blair’s continued quest to lose her virginity to Nate; however, Nate’s goal was to take the virginity of 14-year-old “Jenny, who was in ninth grade at Constance Billard”. Furthermore, as we know, Nate already had sex with Serena, but now, to Blair’s dismay, Nate desired “Jenny [who] was a lowly ninth-grader”. 

Gossip Girl posted that, in preparation for the loss of her virginity, Blair got “a Brazilian wax at the J. Sisters Salon,” because, per Gossip Girl: “After all, no one really wants to go to college a virgin.” 

At Blair’s 17th birthday dinner at Le Giraffe, which was held a whopping three weeks before her actual birthday, 16-year-old “horny” Blair reached under the tablecloth to touch Nate before gulping champagne. Ziegesar wrote:

Blair Waldorf reached under the tablecloth and squeezed Nate’s knee. The candlelight was making her horny. If only Daddy knew what we’re planning to do after this, she thought giddily. She clinked glasses with her father and took a giant gulp of champagne.

Before Nate met Jenny, he was aroused by the idea of seizing Blair’s virginity. Nate observed that Blair looked so hot that she appeared to have already had sex “many times”! Ziegesar wrote:

Nate watched her go. She looked hot in her new black silk halter top, with her straight, dark brown hair hanging between her bare shoulder blades, and her skintight leather pants hugging her hips. She looked like she had already done it, many times. 

Consequently: “Nate was anxious to get back to Blair’s house.” And as for Blair, after some birthday dinner steak and champagne: “She couldn’t wait to get out of there. She couldn’t wait to finally do it [...] Blair seemed impatient, hungrier.”

During the dinner, Blair's father gifted her a pair of MANOLO BLAHNIKs “a pair of beautifully crafted pewter leather mules with adorable little kitten heels,” which she planned to: “wear later that night when she and Nate had sex. Those and nothing else. Thanks, Daddy!”

After the birthday dinner, in her Upper East Side bedroom, Blair undressed in her bathroom, strapped on her “Manolos and spritzed herself with perfume.” (Note: In book 1, before Blair planned to have sex with Nate, Ziegesar wrote that “bad girl” Blair spritzed “once between her legs”.). Blair looked at her reflection in her bathroom’s mirror. “She looked confident and ready.” However: “[...] her breasts [were] so small, but whatever.”

After Blair “pushed open the bathroom door”, Nate found “himself immediately turned on” by Blair's young nude body. Consequently: “The crotch of his red-and-white checked boxers stuck out, tentlike.” 

As for Blair, at the sight of Nate’s erection: “She sucked in her breath.” However, Blair's quest to lose her virginity was thwarted once again. That time by the arrival of her mother and Cyrus, her mother’s fiancé.  Ziegesar wrote: “So much for losing her virginity [...]”

(Note: That was the third time that Blair’s quest to lose her virginity was thwarted. Recall in book 1 that Serena, directly and indirectly, prevented Blair from fulfilling her desires.)

After quickly getting dressed and conversing with her mother and Cyrus, in a page straight out of Restless Virgins: Love, Sex, and Survival in Prep School and American Girls: Social Media and the Secret Lives of Teenagers, Blair asked, “Do you mind if Nate and I go back in my room and watch some TV?” Blair asked.

 

“Of course not. You go right ahead,” her mother said, smiling knowingly at Nate.

Cyrus winked at them. “Nighty-night, Blair,” he said. “Night, Nate.”

Clearly, Blair’s mother and Cyrus knew that Blair didn’t really want to “watch some TV”, and Blair and Nate didn’t disappoint, because as soon as the privileged teens got to Blair’s room, Nate slid his hands under Blair’s Yale sweatshirt: “hoping they’d get back to where they’d left off.” Despite her mother and Cyrus being in the next room, initially, Blair thought that she could “go ahead and have sex and millions of orgasms”; however, in the end, due to her mother’s nearby presence, Blair’s sex drive wilted. Ziegesar wrote:

He pulled her toward him and slid his hands beneath her sweatshirt, hoping they’d get back to where they’d left off. He kissed her neck.

[...] She could go ahead and have sex and millions of orgasms even though her mother and Cyrus were in the next room. She could.

Except she couldn’t. Blair wanted her first time to be perfect, and this was anything but. 

Eleanor, Blair’s mother, and Cyrus planned to have their wedding on the Saturday after Thanksgiving at the (fictional) St. Claire Hotel, which happened to be the same day as Blair’s birthday; thus, naturally, Blair planned to lose her virginity on her mother’s wedding day. Blair’s plan was initiated when she asked her mother, “Can you book a suite for me and my friends?” Ziegesar wrote:

Suddenly Blair had an idea. She and Nate could get a suite! What more perfect place and time to lose your virginity than in a suite at the St. Claire on your seventeenth birthday?

Blair put her fork down, dabbed gently at the corners of her mouth with her napkin, and smiled sweetly at her mother. “Can you book a suite for me and my friends?” she asked.

 

“Of course we can,” Eleanor said. “That’s a fine idea.”

Next, Blair informed Nate that she found the perfect time and place for them to “do it.” Ziegesar wrote:

“[...] my mom and Cyrus are getting suites at the St. Claire for their wedding. And seeing how it’s going to be my birthday and everything, I thought that maybe that would be the perfect time for us to … you know … do it.”

When Blair arrived at her penthouse on Seventy-second Street, “she dropped her backpack on the floor of the foyer. [And] [s]he was greeted by an enormous brown boxer, who trotted up and butted his head into her crotch,” which reminded me of the international bestseller My Secret Garden: Women’s Sexual Fantasies. 

Subsequently, “The door to her mother’s bedroom opened and Cyrus Rose came out, wearing his favorite red silk Versace bathrobe [...] He looked very relaxed. “Hello, Blair!” he shouted, shuffling up and wrapping his arms around her in a bear hug.” However, Blair: “[...] didn’t like standing so close to Cyrus when it was very possible he wasn’t wearing anything under his bathrobe.”

In book 2, Blair had three goals: “finish her senior year at Constance”,  “finally do it with Nate”, and “go to Yale”.

In terms of going to Yale, during the interview at the Ivy with Jason, who was described as “a tall, tanned man with gray hair at his temples and sparkling green eyes”, Blair observed Jason’s derriere, and she performed a kino, a pickup artist seduction technique, before she “earnestly” asked Jason for a promise. Ziegesar wrote:

The interviewer, a tall, tanned man with gray hair at his temples and sparkling green eyes, took her hand and shook it. “So glad to meet you. I’m Jason.” He turned and led Blair into his office. His pants were a little tight in the ass, Blair noticed.

Jason put the cap on his pen and tucked it into his shirt pocket. “Er … do you have any questions for me?”

Blair stopped rubbing her toes and put her foot back on the floor. She scooted her chair forward and reached out to touch Jason’s knee. “If you can promise me to let me in early, I promise to be the best student Yale University has ever had,” she said earnestly. “Can you promise me that, Jason?”

And to cap off the interview, Blair earnestly kissed Jason. Ziegesar wrote:

“I’ll see what I can do,” Jason said. He stood up and held out his hand once more. “Thanks so much for coming in.” He shook Blair’s hand. “Good luck.”

Blair wriggled her feet back into her shoes and smiled winningly at him. “See you next fall,” she said.

And then she stood on tiptoe and kissed him on the cheek.

Ziegesar added that Blair’s: “[...] interviewer definitely wasn’t going to forget that kiss anytime soon.”

In preparation for her, at least, fourth attempt at losing her virginity, Blair was determined, because it was: “[…] her birthday, and tonight she was going to lose it to Nate in that [St. Claire Hotel suite] bed.” Thus, the day before: “[...] she’d been waxed, plucked, exfoliated, steamed, and moisturized from her hair follicles down to her toenails at the Aveda Salon and Spa on Spring Street.” Consequently: “Nate wasn’t going to be able to keep his hands off her tonight.”

In the suite, Blair donned a “Chloé dress [that] fit her body like a condom”, because she was wearing “absolutely nothing underneath” except for a pair of “lace-top stockings”. Consequently, Ziegesar described (17-year-old) Blair as a “bouquet-carrying sex machine”.

After the wedding ceremony, “on the sidewalk on First Avenue, across from the UN,” Blair shared with Nate, “I’m not wearing any underwear.” 

During the wedding reception, which was held “in the elegant ballroom of the St. Claire Hotel”, “Blair tilted forward in her chair and scooped up her champagne flute, downing its contents in one giant gulp.” Why? Because: “[...] she was finally going to lose her virginity to Nate, [and] she wanted to be relaxed.”

However, after bulimic Blair vomited her quenelle, had a smoke, and “spruce[d] herself up”, she discovered Nate: “In the corner [...] kissing a little ninth-grade girl from Constance Billard.”  Ziegesar wrote:

After throwing up her quenelle, Blair had gone outside to smoke a cigarette [...] and headed back to the ladies’ room to spruce herself up.

As soon as she rinsed out her mouth, smoothed down her hair, put on another coat of M•A•C Spice lipstick, and spritzed herself with perfume, she was going to find Nate and take him upstairs to their suite. Enough was enough. It was her birthday and she wanted it her way.

But as she passed through the bar on the way to the ladies’ room, Blair stopped dead. In the corner, Nathaniel Archibald—her Nate—was kissing a little ninth-grade girl from Constance Billard.

Instead of having sex in the suit with Nate, Blair had a sleepover with Serena, where they considered watching pornos and ordering beer, but they watched Breakfast at Tiffany’s. Ziegesar wrote:

Nate and I were supposed to have sex in here tonight,” Blair said, flopping onto the bed in her hotel suite and kicking off her shoes. 

Serena decided not to rub it in by asking Blair what had gone wrong. She pulled her dress off over her head [...] Wearing only her skimpy white satin La Perla underpants, she walked into the bathroom [...] She came out carrying an extra robe for Blair.

Blair took the robe and wriggled out of her dress. “Don’t look,” she warned. “I’m not wearing any underwear.”

Serena walked over to the TV and clicked it on. “I wonder if they get the Playboy channel here. We could watch pornos and order beer from room service,” she joked. She carried the remote over to the bed and sat down.

Breakfast at Tiffany’s was only just getting started.

(Note: In Truman Capote’s Breakfast at Tiffany’s novella, when Holiday Golightly was 13-years-old, she married a [much] older man, when she was barely 15, she lived with a college jock, and when she was 18, she stated, “I can’t get excited by a man until he’s at least forty-two.”) 

Of course, that wasn’t their first sleepover. For instance, and once again from a page out of the international bestseller My Secret Garden: Women’s Sexual Fantasies, during sleepovers, which happened “every weekend”, Blair and Serena took baths together. In addition, they practiced kissing, and they prankcalled their biology teacher. Ziegesar wrote:

When they were younger, Blair and Serena had taken baths together. They’d had sleepovers every weekend, during which they practiced kissing on pillows, made prank calls to their nerdy seventh-grade bio teacher, and stayed up all night giggling. Serena had been there for Blair when she got her period at the end of eighth grade and was terrified of tampons. They’d gotten drunk for the first time together.

Further reading: GOSSIP GIRL [Book 1] Recap (Part 1): Serena

"Teenage Enema Nurses in Bondage" in Salacious “Less Than Zero” Novel

Here’s the synopsis posted on Goodreads for Bret Easton Ellis’ salacious Less Than Zero (Simon & Schuster, 1985):

[18-year-old] Clay, a freshman at an Eastern college, returns home to Los Angeles for Christmas break, but feels totally disconnected and aimless there, and discovers a seamy world of drugs and [teen] prostitution

Back in 2017, I saw Less Than Zero listed on a “12th Grade English: Summer Reading Assignment” for students at an “above average” Manhattan high school, located in the Gramercy Riffs' old neighborhood, where over a third of the students are white, 15% are Asian, and (only) 10% are African-American.

Junot Diaz's Pulitzer Prize winning novel, The Brief Wondrous Life of Oscar Wao, was on the list too. In Diaz's novel, 13-year-old Ana Obregon is: "[...] a pretty loudmouthed gordita who read Henry Miller [e.g. Sexus] while she should have been learning to wrestle logic problems." Ana was introduced to Henry Miller by her 24-year-old boyfriend. Before Ana’s boyfriend left the East Coast to join the military: "He used to read passages to her all the time”. Consequently, Ana shared, “That made me so hot."

However, unlike The Brief Wondrous Life of Oscar Wao, the summer reading assignment teacher added the following disclaimer to Less Than Zero: "Note that this novel contains some disturbing content, including rape and drug use." However, the disclaimer didn’t prepare me for the fact that in Less Than Zero not one, not two, not three but four schoolgirls were raped, which made Vogue magazine’s recent post “Strap In: Vogue’s Next Book Club Pick Is Less Than Zero” (July 23, 2026) intriguing.

Clay’s Salacious Sisters

Before recapping the shocking schoolgirl rapes scenes in the novel, it’s relevant to discuss Clay’s younger sisters whom were described as blond and (approximately) 13 and 15. Unlike a number of teen girls who kept posters of teen heartthrobs on their walls, Clay’s sisters had “different GQ cutouts” of men “pasted on the wall” of their baronial bedroom.

After shopping in Beverly Hills, Clay joined his sisters and his mother in the family Mercedes. While their mother drove, Clay’s sisters discussed another prep schoolgirl whom was an 8th grader at Harvard-Westlake and who was going out with a 9th grader whom one of Clay’s sisters described as “the biggest babe”. Consequently, Clay’s ≈ 15-year-old sister wondered, “I wonder if he’s for sale.”

Still in the Mercedes, Clay’s ≈ 13-year-old sister asked for a Galaga video game for Christmas. After their mother suggested that the Galaga be put in Clay’s bedroom, one of the sisters yelled, “Bullshit! No way. Clay can’t have the Galaga in his room. He always locks his door.”

Clay’s sisters asked him several times about why he locked his bedroom door. Clay shockingly responded by accusing his middle school sisters of stealing his cocaine.

“Mom, tell him to answer me. Why do you lock your door, Clay?”

I turn around. “Because you both stole a quarter gram of cocaine from me the last time I left my door open. That’s why.”

Clay’s sisters didn’t immediately respond to their brother’s accusation. Instead, they asked their mother to turn the volume up, because Killer Pussy's "Teenage Enema Nurses in Bondage" was playing on the Mercedes’ radio. Here's an excerpt from the lyrics :

Teenage, green age, awkward in-between age

(Teenage enema nurse)

I turned fifteen, thought it was a teen scene

(Teenage enema nurse)

Thought it would be easy, but it makes me queasy

I'm a teenage enema nurse

They told me, "Stick the nozzle in

There's really nothing to it

It's not a very pretty job

But someone's got to do it"

Curiously, per the Phoenix New Times article “Killer Pussy: Old-School Phoenix Punk Parodists Gather For 30th Anniversary Reunion” (May 27, 2010), in 1982, "Teenage Enema Nurses in Bondage" was the second most played song on L.A.’s KROQ.

As for Clay’s cocaine theft accusation, after the family arrived home, Clay’s 13-year-old sister exclaimed out by the pool, “That’s bullshit. I can get my own cocaine.”

After Clay’s father was picked up “at his penthouse in Century City”, the family had Christmas Eve dinner “in the main room at Chasen”, where Clay’s sisters “look[ed] bored and tan and talk[ed] about anorexic friends and some Calvin Klein model” as they held their “glasses up by the stem and drink the[ir] champagne slowly”.

One morning, Clay’s sisters, while donning bathing suits in their mother’s large bed, blared Duran Duran, perused men in old GQ magazines, possibly for content to paste on their bedroom walls, and they watched porn; however, one of Clay’s sisters shared that “she hates it when they show the guy coming.” Ellis wrote:

I get up late the next morning to the blare of Duran Duran coming from my mother’s room. The door’s open and my sisters are lying on the large bed, wearing bathing suits, leafing through old issues of GQ, watching some porno film on the Betamax with the sound turned off. I sit down on the bed, also in my bathing suit, and they tell me that Mom went out to lunch and that the maid went shopping and I watch about ten minutes of the movie, wondering whose it is—my mom’s? sisters’? Christmas present from a friend? the person with the Ferrari? mine? One of my sisters says that she hates it when they show the guy coming and I walk downstairs, out to the pool, do my laps.

While sitting poolside with their mother, apropos of nothing, one of Clay’s sisters informed him, “Anyway, I’m having ON [TV] put on the cable.” Coincidentally, per Wikipedia, at its peak in 1982, L.A. was ON TV’s most successful market, which was largely due to ON TV’s adult programming option (i.e., porn).

Shocking Schoolgirl Scenes

As for the shocking schoolgirl rapes scenes in Less Than Zero, at a party in Malibu, Clay and partygoers watched a snuff film that was purchased for $15,000, where a nude, “maybe” 15-year-old girl, had “each foot tied to a bedpost” while a “fat black guy” with a “huge hardon” laid her; however, the young partygoers debated whether or not the fat black guy really killed the schoolgirl with an ice pick, wire hanger, and “thin, large knife”. Ellis wrote:

Everyone in the room is looking up at a large television screen [...] There's a young girl, nude, maybe fifteen, on a bed, her arms are tied together above her head and her legs spread apart, each foot tied to a bedpost [...] The camera cuts quickly to [...] this fat black guy, who's also naked and who's got this huge hardon [...] he has sex with the girl and then walks off the screen.

It's a snuff film, but the viewers at the party debate whether or not the Black man really killed the nymphet with "an ice pick, and what looks like a wire hanger and a package of nails and then a thin, large knife".

Later in the novel, while visiting Daniel, Clay learned from Daniel that a girl, “pretty and sixteen”, was drugged by her 17-year-old drug dealer before she was taken to a party, possibly in the Hollywood Hills, where she got “gangbanged by the entire party”. Ellis wrote:

"She's pretty and sixteen and [...] she goes to Westward Ho on Westwood Boulevard and she meets her dealer there [...] And this guy spends all day shooting her full of smack again and again..."

"And then he feeds her some acid and takes her off to a party in the hills or in the Colony and then...and then..." Daniel stops.

"And then what?" I ask, handing him back the joint.

"And then she gets gangbanged by the entire party."

Subsequently, Clay visited Rip's apartment in Wilshire, where Shandra, a “really young and pretty” 12-year-old girl, who attended Our Lady of Corvallis, a Catholic girls’ high school in Studio City, had her legs spread and tied to the bedposts. Consequently, Clay could see that Shandra’s “cunt” had been recently shaved. Although, Clay was informed that Shandra was “tight”, Clay declined to lay the schoolgirl; however, Trent, Clay’s friend from high school, had his way with the subdued schoolgirl. Ellis wrote:

"[at] Rip's apartment in Wilshire, he leads us into the bedroom. There's a naked girl, really young and pretty, lying on the mattress. Her legs are spread and tied to the bedposts and her arms are tied above her head. Her cunt is all rashed and looks dry and I can see that it's been shaved. She keeps moaning and murmuring words and moving her head from side to side [...]"

Rip says something.

"She's twelve."

"And she is tight, man," Spin laughs.

"Her name is Shandra and she goes to Corvalis" is all Rips says.

And readers learned from Clay that after a “young girl from San Diego” attended a party in Palm Springs with kids from L.A., San Francisco, and Sacramento, she was “raped repeatedly” and fatally mutilated. Ellis wrote:

A young girl from San Diego who had been at the party had been found the next morning, her wrists and ankles tied together. She had been raped repeatedly. She also had been strangled and her throat had been slit and her breasts had been cut off and someone had stuck candles where they used to be. Her body had been found at the Sun Air Drive-In hanging upside down from the swing set [...]

Clay, Blair and the Drunken Blond Girl

Blair was Clay’s girlfriend in high school. Blair was described as having “long blond hair”, she lived in Beverly Hills, and she was a freshman at, what she termed, “the University of Spoiled Children” and “Or Jew . S.C.” (i.e., University of Southern California). Blair and Clay had sex for the first time before they left for college. (Presumably, in high school, but you never know.) It happened in Clay’s Palm Springs house, where Blair’s body was “tan and wet, lying against cool, white sheets.”

However, during the novel, Blair and Clay’s relationship was strained. Consequently, in addition to having sex with Blair, Clay hooked up with another girl. For example, at the After Hours night club, a drunk girl, sixteen and tan, sat next to Clay with her hand on his lap.

After Clay returned from the bathroom, where he did not “do any of the coke”, “the drunken blond girl [...] and Blair are talking about S.A.T. scores.” After Blair appeared to leave the club with “two blond girls”, Clay and the girl danced, and the girl whispered to Clay that maybe they should go to her place, where in her bedroom, Clay and the girl undressed, and she had Clay don a pair of Wayfarer sunglasses and masturbate using Bain De Soleil as lube. The girl masturbated using Bain De Soleil as lube as well. After Clay shared, “I’m going to come,” the girl asked him to “hold on a minute”, because she was “almost there”. To get there completely, the girl “move[d] her hand faster, spreading her legs wider, leaning back against the pillows”.

After they both arrived, the girl,l “flushed”, turned on MTV, handed Clay “a box of Kleenex”, lit a cigarette, and told Clay to be “quiet walking down the stairs”, so he wouldn’t “wake her parents.” Ellis wrote:

[...] we go to her room and I take off my clothes and lie on her bed and she goes into the bathroom [...] she finally comes out, a towel wrapped around her, and sits on the bed [...] she tells me to lean against the headboard and I do and then she takes off the towel and she’s naked and she reaches into the drawer by her bed and brings out a tube of Bain De Soleil and she hands it to me and then she reaches into the drawer and brings out a pair of Wayfarer sunglasses and she tells me to put them on and I do. And she takes the tube of suntan lotion from me and squeezes some onto her fingers and then touches herself and motions for me to do the same, and I do [...] after this goes on for a while I tell her that I’m going to come and she tells me to hold on a minute and that she’s almost there and she begins to move her hand faster, spreading her legs wider, leaning back against the pillows, and I take the sunglasses off and she tells me to put them back on and I put them back on and it stings when I come and then I guess she comes too. Bowie’s on the stereo and she gets up, flushed, and turns the stereo off and turns on MTV. I lie there, naked, sunglasses still on, and she hands me a box of Kleenex [...] She lights a cigarette and I start to dress. And then I call a cab and finally take the Wayfarers off and she tells me to be “quiet walking down the stairs so I won’t wake her parents.

Less Than Zero was, unsurprisingly, a major bestseller, but I would have to agree with Michiko Kakutani’s review in The New York Times that the novel was “disturbing” and that it had an “unnerving air of [a] documentary”. Kakutani wrote: “One of the most disturbing novels I’ve read in a long time. It possesses an unnerving air of documentary reality.”

The Courtney Stodden (17), Doug Hutchison (52) and 'Seinfeld' Star (53) Age-Gap Scandal

Below is Courtney Stodden and Doug Hutchison’s age-gap relationship timeline that’s partially based on an A&E report.

January 2011: Courtney Stodden Meets Doug Hutchison

In 20211, 16-year-old Courtney Stodden, a pageant contestant, model, and aspiring singer, enrolled in 50-year-old Doug Hutchison’s online acting workshop. (Doug is arguably best known for his roles on The X-Files and Lost.) Subsequently, after class, Courtney and Doug began exchanging flirtatious emails.

Due to Courtney’s age, Krista Keller, Courtney’s mother, monitored the emails, which she told The Daily Beast were "beautiful, loving, [and] nonsexual." However, Doug didn’t realize that Courtney was a teen, and when he found out, he shared with ABC News that the news caused a "struggle" in his heart, because he had "already started falling for her."

May 20, 2011: Courtney Stodden and Doug Hutchison Get Married

Per A&E, Courtney’s mother said that Doug: “offered to step away from Stodden until she was 18, but Keller suggested that they should just get married instead.” Courtney’s mother opined that her daughter, despite his age, had “real love” with Doug. In addition, Courtney’s mother knew that due her daughter’s “sexuality and because of the attention she gets” no regular man could handle her daughter. Courtney’s mother said,

"Even though she was just 16, I knew it was going to take a pretty big man to handle her because of her sexuality and because of the attention she gets."

Consequently, 16-year-old Courtney and 51-year-old Doug got married in Las Vegas, and the age-gap couple honeymooned at the Chateau Marmont in Hollywood.

2012–2013: Couples Therapy, and The Donny Clay Show with Courtney Stodden

Courtney and Doug appeared on VH1's Couples Therapy with Dr. Jenn Berman. Per A&E “([...] the fact that Stodden wasn't even 18 yet) caused a lot of tension both within the cast” ; however, Dr. Berman informed Access Hollywood that in her professional opinion “she didn't see [Doug] Hutchison as a predator.”

In the promotional interview for Couples Therapy with Billy Bush, Doug mentioned that his age-gap relationship with Courtney was modeled after John and Bo Derek, whom I wrote about in The Allure of Nymphets, where I related that Bo had to avoid being prosecuted for statutory rape after he bedded the 16-year-old future 10 star by fleeing the country to Germany until Bo turned 18. Doug mentioned in the interview that John and Bo were married for 22 years and that Bo held John's hand on his deathbed.

I was shocked by Billy Bush's defensive, harsh, and antagonistic attitude towards Doug during the Couples Therapy segment. Not once did Billy praise Doug for getting Courtney's parents’ blessing and for waiting to have sex with Courtney until after they were married. However, Billy only chuckled during ”Grab ’em by the Pussy” Gate.

In addition, Doug mentioned the age-gap relationship between Celine Dion and René Angélil. Doug related that 38-year-old René met Celine when she was 12. René and Celine began a(n) (open) relationship when Celine was 20. And they eventually wed and were married for over 20 years until René’s death.

During the Couples Therapy segment, Courtney shared with Billy that, despite being 16, she knew what she wanted and that Doug, despite being 51, was the love of her life. Coutney shared:

“I knew what I wanted [...] I wanted to save myself until I was married [...] That meant so much to me that I found the love of my life. I married him at 16. I knew what I wanted.”

In 2012, Courtney and Doug appeared on Funny or Die’s “The Donny Clay Show with Courtney Stodden”. On the episode, while Doug looked on encouragingly, Courtney posed in a red bikini while Donny Clay (Jason Alexander) examined her 17-year-old breasts with a mobile phone.

Recently, Courtney posted on Instagram (July 20, 2026) that, in hindsight, it’s “impossible” for her to understand how Jason Alexander was allowed to “repeatedly” rub his phone across her teen breasts, because she was a minor and she didn’t have any “legal power”. Courtney posted:

I was 17 years old in this photo. The older I get, the more impossible this is to understand. During this comedy sketch, Jason Alexander repeatedly rubbed his phone across my breasts while saying there was “no signal” in my head but “plenty of signal” in my chest. Later in the sketch, he joked that when I turned 18 he’d like to take me behind the couch and “have his way” with me. IMDb credits him as one of the writers of the episode. As an adult, that fact has become harder—not easier—for me to understand. I was a minor. I didn’t have the legal power to decide whether I wanted to participate. The contracts were signed by adults. The paycheck went to Doug. The production moved forward. I was the only child in the room.

Looking back now, I don’t see comedy. I see a 17-year-old girl whose body became part of an adult joke. People still say, “You chose to be there.” Legally, I couldn’t make those decisions for myself. That’s the point. I can’t change what happened to me but I can ask myself: How did so many adults look at a minor and decide this was acceptable? [...]

Per TMZ, Jason Alexander apologized to Courtney by stating: "Looking back at the comedy sketch in which Ms. Stodden and I participated in 2012, I completely agree that it was inappropriate and I truly regret it."

Rhetorical question: Would Courtney condone having her breasts rubbed by Jason Alexander if she were 18?

November 1, 2013: Celebrity Big Brother and The First Split

A few months after Courtney appeared on Celebrity Big Brother and after almost three years of marriage, Courtney and Doug separated. Courtney shared with E! News that their age-gap was the main cause of the separation. Courtney said, “When I was 16, I got my marriage license instead of my driver’s license, come on!” However, less than a year later, Courtney and Doug were back together, and they made plans to renew their vows.

2015–2016: Sex Tape 

In May of 2015, Vivid Entertainment released Courtney Uncovered: The Courtney Stodden Sex Tape, which was a solo sex tape made by Courtney “for charity” in which by then-20-year-old Courtney engaged in explicit auto-stimulation.

May 2016: The Vow Renewal and Pregnancy

In May of 2016, Courtney announced that she was four weeks pregnant and that to celebrate their fifth anniversary, she and Doug would have a vow renewal; however, Courtney lost the baby.

2016–2020: The Final Split

Courtney and Doug separated again in 2016, and signed divorce papers in March 2018. Consequently, in January 2018, due to depression and anxiety, per A&E, Courtney, via an Instagram post, begged Doug “for [a] reconciliation, but their separation continued.”

In April 2019, Courtney shared with “BuzzFeed News that she was taking her time with the divorce because she still loved Hutchison.” Courtney shared:

“I know that I love him so much, and I think he’s also ingrained in me because I was 16,” she said. “He has his thumbprint all over my spirit, and that part is hard for me to grow out of. He’s in my identity. If he wasn’t the person he is, I would say absolutely he took advantage of me. But the situation was so unique, right or wrong.”

However, after almost nine years, their divorce was finalized in March 2020.

In their first interview after they were married, Courtney informed an ABC News reporter that she was a virgin when she married Doug and, consequently, God rewarded her with a gift, her soulmate Doug. Courtney said,

“I was a virgin when I married him. I knew that if I kept that I would really be blessed with a gift. And God did. He blessed me with my soul mate.”

However, in a more recent interview with ABC News (March 21, 2025) report “Courtney Stodden reflects on grooming claims and being a teen bride”, Courtney related that, although she was in love with Doug, it was only because he groomed her by making her feel happy and special.

Courtney, “When you’re in love and you're underage, you’re like, ‘Oh, this is my first love!’”

ABC News reporter, “Were you in love?”

Courtney, “I thought I was. I was in love with what he groomed me into believing was true [love]. And I was in love with feeling so happy. Feeling so special.”

Thus, it’s safe to infer that if Courtney were 18 and Doug made her feel so happy and so special, she would not have considered it to be grooming, which is intriguing considering the fact that, per Courtney’s mother, Doug: “offered to step away from Stodden until she was 18”.

GOSSIP GIRL [Book 1] Recap: “34D” “Slutty Sex Goddess” Jenny Humphrey (Part 3)

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)