In book 1 of Gossip Girl, Cecily von Ziegesar wrote that Blair Waldorf “Turned seventeen on Bastille Day” and that Blair was “pretty hot” with “long, dark brown hair” who could easily go from a “proper preppy” schoolgirl to a “sex kitten”. Ziegesar wrote:
“Blair tucked her long, dark brown hair behind her ears and swigged her mother’s fine vintage scotch from the crystal tumbler in her hand. She was already on her second glass.”
That summer Blair: “Turned seventeen on Bastille Day [...]”
Blair could go from “proper preppy” to “her trashy, pointed, knee-high boots and that sexy metallic skirt her mother hated. Poof—rock star sex kitten. Meow.”
In terms of (underage) drinking (of expensive scotch), Blair and her Upper East Side friends could drink “whatever they wanted, whenever they wanted”, and they could have teen “sex or [do] drugs—as long as” they “kept up appearances”. Ziegesar wrote:
Luckily Blair and her friends came from the kind of families for whom drinking was as commonplace as blowing your nose [...] Blair and her friends could drink whatever they wanted, whenever they wanted, as long as they maintained their grades and their looks and didn’t embarrass themselves or the family by puking in public, pissing their pants, or ranting in the streets. The same thing went for everything else, like sex or drugs—as long as you kept up appearances, you were all right.
At the dinner party in the Waldorf penthouse, which had a view of Fifth Avenue and Central Park, Cyrus Rose, Blair’s soon-to-be father-in-law, asked 17-year-old Nate, in reference to Blair, “You sleep with her yet?” Consequently, “Nate turned redder than the upholstery on the eighteenth-century French chaise next to him.”
That previous Easter, in a hotel room, Blair gifted Nate a “moss-green cashmere V-neck sweater”, which “looked so good on him that Blair wanted to scream and rip all her clothes off.” Really?
Subsequently, they kissed, Nate pulled Blair onto the hotel bed, and he undressed her.
They kissed for a long time [...] Nate twined his fingers in Blair’s hair and pulled her down on the hotel bed.
Blair put her arms above her head and let Nate begin to undress her [...]
And two nights prior to the dinner party, in Blair's bedroom, Nate: “[...] had lain down on her bed and murmured, “I want you, Blair.” However, on both occasions, they did not have sex, because Blair wanted to wait until she turned 17, but after “another sip of her scotch” at the dinner party, 16-year-old Blair “was definitely ready.” Ziegesar wrote:
Blair wasn’t trying to be a tease, she just wasn’t ready.
She had wanted to wait to have sex until her seventeenth birthday next month.
But now [at the dinner party] she was through with waiting.
And, just like that, Blair knew she was ready. She took another sip of her scotch. Oh, yes. She was definitely ready.
“Don’t forget to use protection,” Chuck [Bass] called, raising his glass at Blair and Nate as they turned down the long, red-carpeted hallway to Blair’s bedroom.
“I’m about to have sex with Nate [in my bedroom, during my mother’s dinner party],” Blair “thought giddily,” but to Blair’s dismay, Serena arrived at the dinner party, which meant that Blair had to wait again.
Determined to have sex, Blair emailed Nate, via her prep school email address, to inform him that she really wanted him to spend the night in her bedroom.
TO: narchibald@stjudes.edu
FROM: blairw@constancebillard.edu
Dear Nate.
I miss you. Monday night was supposed to be really special. Before we got interrupted [...] I just wanted to tell you that I’m ready to do it [...] My Mom and Cyrus are going away on Friday and I really want you to sleep over. I love you. Call me.
Love,
Blair.
Consequently, readers learned via a Gossip Girl (i.e., Ziegesar) post that Blair went to the Zitomer Pharmacy to purchase a pack of Lifestyles Extra-Long Super-Ribbed condoms. Gossip Girl surmised that Blair knew to get Extra-Long condoms, because Blair and Nate previously “had done everything but.”
After leaving Zitomer’s, Blair went to J. Sisters for a painful Brazilian bikini wax, which Gossip Girl opined, “But believe me, it’s worth it.”
Blair planned to: “knock back a few drinks” (i.e., “Ketel One and tonic. Extra limes”) with Serena in the Star Lounge in the Tribeca Star Hotel and then: “leave early, go home, fill her room with candles, take a bath, and wait for Nate to come. And then they’d have [“wild”] sex all night long [...]”
After Blair told her doorman to send Nate up, she got naked, and the “bad girl” spritzed “once between her legs.” Ziegesar wrote:
“Yes, send him up,” she told the doorman. She unbuttoned her jeans and flew back to her room, wriggling out of them. Then she pulled the rest of her clothes off and tossed them into the closet. Naked, she spritzed herself with her favorite perfume, even spritzing once between her legs.”
Oooh, bad girl.
Once Nate entered the penthouse, with no need for foreplay, Blair demanded, “Just hurry up and take your clothes off.” Blair was ready. Her bedroom was “a blaze of candles”, she had chilled red wine, and she was beautifully naked. Ziegesar wrote:
Blair’s room was a blaze of candles. A bottle of red wine was open on the floor, with two glasses beside it. Blair knelt down and poured each of them a glass like a little geisha. She felt more comfortable naked in the darkness of her room.
She was naked, and she was beautiful.
Upon seeing Nate’s (teen) erection, which Ziegesar wrote “looked like it was going to take over the world’, Blair murmured, gaping at Nate’s hard-on, “What about a condom or something?”
However, once again to Blair’s dismay, before they could have sex, Nate shared with Blair that he had sex with Serena. Consequently, Blair called Serena a “nasty, slutty bitch”, Nate “pathetic”, and Blair demanded, “Get the fuck out [...]” Ziegesar wrote:
“Blair threw the quilt off her shoulders and stood up. “I knew it!” she shouted. “Who hasn’t had sex with Serena? That nasty, slutty bitch!”
“I’m sorry, Blair. But it wasn’t like, planned or anything,” Nate said. “It just happened. And it was only that one time, promise. I just didn’t want you to think this was my first time, when it wasn’t. I had to tell you.”
“Get the fuck out of here, Nate,” she said, angry tears sluicing her cheeks. “I can’t even look at you. You’re pathetic.”
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Gossip Girl had a very interesting take on what happened or did not happen between Blair and Nate. In THE VIRGIN ISSUE post, Gossip Girl wrote that Nate’s behavior was unbelievable and not worthy of admiration, because he was “thisclose to getting a nice slice of B pie”. And Gossip Girl wrote that, in reality, Blair would have preferred that Nate “kept his mouth shut” and not have been morally conscious about sharing that he previously had sex with Serena, whom just happened to have been Blair’s (previous) best friend. Gossip Girl assumed (correctly) that a boy would do “anything to bag a virgin.” Gossip Girl posted:
Can you believe N? He was thisclose to getting a nice slice of B pie, if you know what I mean. I guess we’re supposed to admire his self-control, his ability to keep the old hot dog in the bun. But I bet B really wouldn’t have minded too much if N had just kept his mouth shut and got on with it instead of getting all moral on her and telling her all about his time with S. I mean, who’s B going to lose it to now?”
“I was wrong about boys. I always thought they’d do anything to bag a virgin. I mean, I thought N would like the idea that B has never done it [...] So disappointing.
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Serena and Blair
Prior to their teen love triangle with Nate, Serena and Blair had been best friends. For example, in addition to enjoying “cocktails at the Star Lounge in the Tribeca Star Hotel”, they would smoke cigarettes and drink Coke in Central Park during the school day. After school, they would “pee in the downstairs entrances to their classmates’ brownstones and then ring the doorbells and run away.” Ziegesar wrote:
She [i.e., Serena] and Blair would walk to school together, spend Double Photography in Sheep Meadow in Central Park, lying on their backs, taking pictures of pigeons and clouds, smoking and drinking Coke [...] They would have cocktails at the Star Lounge in the Tribeca Star Hotel again [...] They’d pee in the downstairs entrances to their classmates’ brownstones and then ring the doorbells and run away.
And readers learned via the Gossip Girl post S AND B: HOT IN THE HOT TUB! that Blair and Serena shared a girl-on-girl kiss in the hot tub in Chuck’s Tribeca Star Hotel suite; however, Gossip Girl didn’t know if the kiss was serious or silly. Gossip Girl posted:
[...] back when they were still tight, S and B shared a hot hot-tub moment together in C’s suite in the Tribeca Star. Was the kiss an expression of their true feelings for each other? Or were they just messing around like two silly drunk girls?
The kiss happened “during a very drunken night at the end of 10th grade”; thus, Serena and Blair were ≈ 16-years-old. While they were “soaking in the hot tub”, “Blair had kissed Serena full on the lips.” However, due to being inebriated, Serena didn’t appear to remember the kiss, but “Blair never forgot it.”
Lastly, in addition, based on the photographs that Chuck kept in the suite, Blair was naked when she kissed nude Serena in the hot tub. Ziegesar wrote:
“On the coffee table in the living room was a pile of photographs.”
“Blair, Nate, Chuck, Isabel, Kati, everyone was in them, naked in the hot tub, dancing in their underwear, drinking champagne in bed. They were all party shots from last year—the date was in the corner of each one—and they were all taken in the suite.”
