AN: I probably shouldn't be starting a new fic but I was hit with this idea and wanted to write it all before I lost the momentum. I have 90% of this story written and it looks like it'll be about 20k words. I just need to write the last chapter :) So it should have pretty regular/frequent updates.
A profuse thank you to my wonderful beta, asadair, is in order as she not only helped to make this chapter more colorful but also to fine-tune it.
Thank you for reading this new story, I hope you'll all enjoy this trope-y premise!
PS. I made an aesthetic for this fic which can be seen on AO3 or tumblr (thedairarchives).
As Blair Waldorf waves off another suffocating cloud of smoke and swivels around on her bar stool to scowl at the tattooed offender, she contemplates her own sanity. Letting her best friend, Serena van der Woodsen, choose the location of this year's annual sleepover had clearly been a massive lapse in judgment. Her eyes shift over to where Serena is brushing a strand of blonde hair from her shoulder coyly as she flirts with the businessman who's been buying her drinks all night. Blair has half a mind to remind Serena that the main event of the annual sleepover starts in approximately twenty minutes but thinks better of it. If she gives her too much time to think, she'll come up with a dare that might actually be challenging.
In Blair's opinion, the most important part of every annual sleepover is the obligatory high stakes round of Truth or Dare. It is no ordinary round of the classic game. Suggest eating mustard and you would be officially banned from ever attending again, as Blair had told the girls many a time. No, there would be real-life consequences. Like the marriage Blair accidentally broke up one year when she kissed that guy with the wedding ring tan she helpfully pretended not to see.
This year would be no different. Sure, the annual sleepover almost didn't happen because Serena and Blair had spent four months out of this year not speaking after another fight. But what else was new? Best friends always fought and Blair wouldn't let that stop a tradition. She had already come up with a list of twelve winning dares that were certain to get at least one of the other girls arrested or banned from ever returning to Las Vegas.
"Ugh," Isabel groans as she walks up to Blair at the bar. "Kati and I just did a full loop of this place and there's not one cute guy, besides the one Serena already snagged." She shoots an envious scowl in Serena's direction.
"Don't fret, ladies," Blair feigns assuredness. "The night is young and if you all survive tonight's vicious round of truth or dare we can stop by the VIP-only lounge above Altitude. There'll be more suitable options there."
Blair glances over at S with an eye roll, watching her place her arm on the guy's arm. The intimate gesture gives her another flash of Serena entangled with Nate and she has to push the thought away to stop her blood from boiling. She still isn't completely over the fact that Serena and Nate had apparently lost their virginities to each other before Serena left for boarding school freshman year. That little revelation had come out the year Serena had returned to Constance Billard for senior year and six years later, it still wounds her.
Since finding about Serena's betrayal, their friendship had been admittedly strained with things reaching a new tension point when Serena had gotten into Yale, Blair's dream school and Blair had only gotten into Columbia.
So maybe Blair got the occasional urge to rip out Serena's too shiny blonde hair every now and then, but she couldn't just cut her out of her life, no matter how badly she wanted to at times. Serena was her sister, her best friend since birth, she couldn't end a connection like that.
Blair senses someone making a move for the empty bar seat to her left, deserted by Kati after she and Isabel claimed they needed to touch up a makeup refresher. She turns to glare at whoever it is and tell them to fuck off but stops short when he speaks. "Sorry, is, uh- Is this seat taken?"
The guy is not what she expected in a Vegas bar, she thought whoever it was would be a carbon copy of the man currently inching closer to Serena, another suited sleazy Wall Street-type here for a weekend of sin. Instead, the guy wears a slightly wrinkled tee shirt layered under a grey blazer and paired with slim fit dark jeans. She glances down at his shoes, Chelsea boots, hipster indeed. He doesn't belong and Blair has a flash of empathy for him because she too, should be anywhere but here. She can also tell she makes him a little uneasy which pleases her.
"It's not," Her tone is relaxed as she stirs her drink. Blair reminds herself that her own stroke of pleasantry was caused by boredom and nothing more. Plus, Kati had gotten a little too comfortable sitting next to her, clearly trying to edge out Penelope as second in command of the minions. Now, Kati would have to find somewhere else to sit upon returning from the ladies' room.
As Blair takes the last sip of her drink, the bartender materializes in front of her. "Another gin and tonic?"
She nods, deciding she's not quite drunk enough for a proper round of Truth or Dare. Besides, she still has ten minutes to kill, and that's plenty of time to finish her drink and subtly watch this nerd beside her read his book while sipping an Old Fashion.
With mild interest, she turns to look at him, "I always come to Las Vegas to do my reading, too. There's something about the ambiance… Isn't there?"
He looks up from his copy of Cat's Cradle and his brown eyes meet hers. She feels a flicker of something unexpected and reminds herself to steel her gaze a little more. God forbid he gets the impression she's flirting with him.
Before he can answer, Kati and Isabel wedge themselves back by her side. "Is it time yet? Penelope is so desperate for entertainment she's about to dial Nelly's ex because you know how that always cues the waterworks."
"I still don't get why she's here," Isabel chimes in. "In those glasses too. I told her to wear contacts but no, she can't with her astigmatism."
"My mom has astigmatism in both eyes and she wears contacts," Kati replies matter-of-factly.
Blair exhales in exasperation and downs the rest of her drink. She stands and smooths out the skirt of her burgundy jacquard dress. She gives one last glance to the guy beside her who is watching all of this in amusement before marching toward Serena.
"S, it's time." Blair steps between Serena and the businessman, not giving a single fuck about cockblocking this guy after he spent all night buying her best friend drinks. Blair has no doubt he was hoping for at least one night after dropping a couple hundred on her. As Blair clutches Serena's lithe arm, she turns to whisper in the guy's ear with a smirk. "Better luck next time."
"B!" Serena exclaims, "You're bad. Poor guy, you know he bought a bottle of Dom for us."
"Don't care," Blair leads the way toward the booth she reserved in the back for the festivities. It's in the secluded corner of the club where the sound is at least slightly muffled, allowing for somewhat decent (or indecent) conversations. At the center of the table is a few bottles of liquor surrounded by shot glasses.
"Let the games begin!"
The girls all do a shot and then Blair declares that Truth or Dare will proceed in alphabetical order, which means she gets to choose her victim first. "I choose…" She looks around pensively, as though she doesn't know exactly who she will pick. "S,"
She's met with an annoyed expression from Serena that's quickly replaced by a dazzling smile. "Dare, obviously."
Blair feels gleeful satisfaction pulse through her veins as she issues her dare, "I dare you to go steal that guy's room key, without him noticing-"
"Easy," Serena makes a move to get up, shimmying down her too-short silver mini dress.
"I'm not finished," Blair chides. "Then, go up to his room and leave your phone number on the bed and…" She pauses for effect. "That Cosabella g-string you're presumably wearing."
Serena just shrugs, much to Blair's dismay, and slides out of the booth with an airy wave of her hand. "Be back in ten!"
"Watch and learn how it's done, ladies," Blair instructs as they all fixate Serena, who effortlessly glides back over to the man from the bar. She leans in and whispers in his ear and when he turns to face her, he looks like he's just won the lottery, incorrectly thinking his night isn't a waste after all.
As Serena's cascading hair envelops the man's handsome face, she connects their lips. Blair figured she would go this route, it's the most predictable yet practical distraction. Her hands drift up his leg until their in his pocket and swiftly removes her target. She fumbles through it and for a split second, Blair is certain she's about to be caught as the man begins to pull away from her lips.
Then, with a manicured hand, she guides his head towards her neck, granting full access as she holds the wallet within sight and swiftly removes her target. By the time the wallet is back in his pocket, Serena has extracted herself from his embrace. Blair watches as the two have a whispered exchange. Serena gives him one last lingering kiss before sauntering toward the elevator, briefly flashing them all a winning smile.
"So what do we in the meantime?" Nelly asks, pushing her glasses back up on her nose.
Blair pours them all shots of Grey Goose and looks at them with a wicked grin. "Drink up,"
Serena returns ten minutes later, a smug smile on her face. "I hope he likes what he finds…If he ever gets back in. Hopefully, he was wise enough to get two key cards when he checked in. If not, well he'll be spending more of his night at the concierge than he expected. Oh, and I brought us something else."
Serena's hand drifts down towards her bra and she plucks out a sleek black AmEx card. "Drinks courtesy of one Colin Forrester tonight."
"Serena," The minions all exhale in wonder.
"So you're just commando right now?" Nelly asks with wide eyes.
"Actually," Serena smirks, tossing her long hair over her shoulder. "I'm not. I did leave a pair of my skimpiest Cosabella undies behind. But not the ones I'm wearing. You never specified, B."
Blair is instantly annoyed by this twist but presses on. "Okay, Kati's turn!"
Kati perks up and sets her attention on her best friend. "Sorry, Is. I choose you."
Isabel looks unperturbed and calmly selects, "Dare."
The night continues with the minions all daring each other to do things from obtaining the phone numbers of at least five men wearing wedding rings to making out with one of the nightclub bouncers. It's amateur hour, really, Blair thinks to herself. She does another shot to rouse herself before she inevitably gets dared.
The moment comes when Serena's turn arrives, right at the end of the round. Serena has an expression that Blair really doesn't like. That same cutting expression that she had leveled Blair with during their last fight, when she told her that Nate loved her, had always loved her.
Her stomach plummets as Serena's bright blue eyes meet her own surreptitious brown ones. "Blair,"
With an unfazed expression concealing her inner anxiety, Blair answers steadily. "Dare."
Serena smiles as though she's just played right into her hand. "I dare you to marry someone. Here. Tonight."
For the first time in what feels like Blair's whole entire life, victory seems unachievable. Because, of course, Serena always gets what she wants.