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
