we are born lost.
then we're found, but we're all just lost, am i right?
They stumble in as a pack at quarter-past midnight, a whirlwind of couture and high-pitched voices, occupying at least a third of his (semi) reputable establishment. His regulars give him the eye from the moment the door opens, but Dan’s never been the sort to throw out paying customers just because they’re annoying. And they are annoying, nothing like the tame Brooklyn hipsters that have made up ninety-nine percent of his clientele since he started at the bar four months ago, but when a tiny brunette slaps a credit card on the counter and it actually fucking sparkles—
Well. He might be judging her, and he might hate himself for it, but at least he’s not stupid.
“Whiskey,” she slaps the surface of his bar repeatedly, a perfect staccato, and it would almost be intimidating in its ferocity if she wasn’t so fucking small. This is his primary mistake: she catches him off guard, and it only takes a five second pause for him to realize that he knows her—he’s seen her around NYU’s English department, nose stuck in the air. She’d be impossible to forget. “Hello? Are those ridiculous curls impeding your hearing? Whiskey. Whiskey. Whiskey.”
Dan narrows his eyes, focusing in on her stance. It’s a little wobbly, her words mildly slurred, and he glances towards the rest of her group. There’s a blonde with a tiara (bachelorette party, he realizes, which makes a whole lot of sense) giving an empty chair a lap dance—God, fuck, he does not get paid enough for this.
“How many have you had tonight?”
“Zero.” Dan raises an eyebrow, and she huffs. “Plus five. Do you know what the limit on this card is?”
“Probably not high enough to tempt me into overserving you.”
“It doesn’t have a limit. You Brooklynites can be a little slow, so I’ll break it down nice and simple for you,” she speaks as if he’s a third-grader and yeah, he’s definitely asking for a raise after this. “Take the glass. Pour the whiskey. Give it to me. Repeat until I say stop.”
“Okay, yeah, you’re really not making me want to serve you any more right now.”
She stomps her feet.
He can’t help it—he laughs, nothing more than a slight huff of breath, still loud enough that he knows she hears.
“Fine then. I’m the maid of honour at my best friend’s wedding to my ex-boyfriend.” Dan blinks, a little startled, but she continues, “The best man is my other ex-boyfriend, an abusive Basshole who tried to sell me to his uncle for a hotel.”
“What’s a Bassh—wait, your boyfriend tried to sell you?”
“Sell, trade. Same thing. So?”
She rolls her eyes, and Dan feels as though he’s failing some sort of test. What sort of test he can’t possibly figure out, but he’s almost…disappointed in himself, strange enough as it is.
“So I think I deserve the whiskey, thank you very much.”
And—okay, she’s coherent. More than coherent; she’s verbose, her dark eyes remarkably steady and clear, and if it weren’t for the near-imperceptible slur of her words he wouldn’t think she’d had a single drink in the first place. As if sensing his thoughts she does a little twirl, adorable and impressively steady, and Dan knows that he doesn’t really have any good reason to say no. The slight twitch of her lips tells him she knows it, too.
“One whiskey,” he says, “because that was the most impassioned speech I’ve been on the receiving end of in a long time.”
“Not shocking, judging by the decrepit state of your regular clientele.”
Dan raises an eyebrow, amused—why is he amused? By all rights he should be annoyed out of his mind, but this girl is…charming, despite logic telling him that she should be everything but. “They’re hipsters, not heathens. Are you always so judgemental”
She scoffs. “I fail to see the difference.” More taps on the card, one, two, three, ignoring his question, and that seems to mark the end of their conversation. He’s not sure why that disappoints him.
“Coming right up,” he says, plucking the most expensive bottle off the shelf, and she grins.
B. WALDORF, the card says, embossed in silver print, and Dan commits that to memory. He’ll probably never see her again, but even so, B. WALDORF etches a space in his brain ten times larger than any five-foot-two socialite should be able to.
He’s surprisingly okay with that.
The group leaves after half an hour, but she spends the rest of the night sneaking glances at him when she thinks he doesn’t notice.
He does notice, though.
Dan notices everything.
It’s two weeks before he sees her again, wearing a floppy black hat and sunglasses so oversized that he probably wouldn't recognize her if she didn’t stick out like a sore thumb, absurdly overdressed for three o’clock on a Tuesday afternoon. B. WALDORF strides in as if she owns the place, not even flinching as the door slams behind her, stilettos clicking across the floor like a time bomb.
And fuck him, Dan loves it.
“Are…oh my God,” he whispers when she slams her purse down on the bar, overdramatic and overly-smug, but he can’t help it—he honestly didn’t think he’d ever see her again, and he’s kind of delighted to find that he was wrong. “Did someone follow you here? Are you on the lam?”
He doesn’t need to see her eyes to know that she’s rolling them. “You’re attempting to be witty, I know, but I might as well be. Blair Waldorf, willingly setting foot in the rodent-infested Brooklyn streets?” She says the word like a curse, Brooklyn, but Dan barely notices. He’s too busy focusing on her first name, Blair, bouncing through his brain like an echo. “I know you’re the social equivalent of a dust mite, Humphrey, but even you must understand the sort of chaos that would cause.”
He blinks. “You know my name?”
“Don’t get too excited. I’m a Waldorf; knowing people is my birthright.”
“Should I know what a Waldorf is? Is that a type of hotel?”
If looks could kill Dan’s pretty sure that he’d be six feet under by now. “I’ll give you a reluctant pass on that statement, only because I've only been in this neighbourhood for about five minutes and I can already feel myself turning into a cave person.”
“So you looked me up,” he circles back to the topic at hand feeling entirely too smug, entirely unbothered by the venomous glare she’s sending his way. Attempting to send, anyways. The glasses, inexplicably still on her face, dampen the blow quite significantly. “You made a point to learn who I am. I can’t decide if I should be terrified or charmed. Do you have a crush, Ms. Waldorf?”
“On a walking Muppet? Don’t make me gag.”
“So you came all the way out to Brooklyn for…what? A field trip? Espionage?”
Blair snorts, and it’s way cuter than it has any right to be. “I needed to day drink and mourn the pathetic reality of my current situation far away from the prying eyes of anyone who might know me. Anyone of import, I mean.”
“And you chose my bar.”
“And I chose this particular bar,” she says, and Dan can tell that she’s less annoyed than she’s trying to sound because she’s smiling, just a little bit, just enough to count, “because you serve a decent whiskey and there’s no way that a single soul in my social circle would dare set foot in a bar that practically has a neon Typhoid Here! sign hanging above its doorway.”
“I mean, your best friend did choose to here for her bachelorette party.”
“My best friend is an idiot when she drinks.” Blair fiddles with the bracelet on her wrist, polished gold, and Dan knows that he’s struck a nerve. He makes a mental note—no best friend talk unless initiated by Waldorf herself. “I don’t even think she remembers coming here. She puked in the limo on our way to the next bar and spent the rest of the night complaining that none of us ordered strippers.”
“Sounds like a charmer.”
“I’ll take your word for it,” Dan says, and he points to the shelves behind him. “Same as last time?” even though he’s already pouring her drink into the tumbler before she nods in affirmation. When he turns around she’s got Cat’s Cradle open in front of her, and Dan adds another fact onto his rapidly-expanding list of B. WALDORF FACTS: reads Vonnegut. Somehow that doesn’t surprise him.
“You can leave now,” she says, but the words don’t sting quite as much as they should.
(Maybe it’s because she leaves him a sixty percent tip.
She starts coming in every week, sitting at the same spot at the bar, reading a new book and acting as though this is totally normal—as though Upper East Side girls with a remarkable taste in literature and far too much money always find a random Brooklyn establishment to frequent. Dan tries not to read too much into the fact that she never picks one of the empty booths in the back, or the tables by the windows. When it comes to Blair Waldorf he knows better than to assume.
They talk a little bit, five or ten minutes at a time before he places her whiskey, neat, right on the coaster that he plants on the counter right before she arrives. He learns that she works in journalism. He learns that she likes Plath but finds Hughes remarkably overrated. He learns her favourite movie is anything with Audrey Hepburn and that she thinks Gone With the Wind is obscenely overrated.
He doesn’t learn anywhere near as much about her as he wants to, which is annoying both because Dan doesn’t like not knowing things and because he knows that he shouldn’t like her, prim and proper and tied up with a Birkin bag bow.
Dan Humphrey has no reason to like her, Blair Waldorf, the antithesis of everything he’s ever known.
And yet she leaves him a ridiculously good tip every time she comes in and she only comes in when he’s there, only sits in her spot when he’s the one tending bar—he knows because he’s asked her coworkers and none of them have ever seen her, this mysterious girl of immense privilege who seems to be haunting Dan’s dreams. He’d think she was an apparition if he hadn’t found her Instagram profile: over a million followers, even though she has less than twenty posts and only six of them show her face.
Kafka one week, Capote the next. She pretends as though she couldn’t care less about his presence but listens to every word he says. He knows she does because one day he catches her laughing when he makes an (admittedly pretentious) joke to another customer who mentions that Grisham is his favourite author, nose buried in her book, stuck on the same page that she’s been staring at for the last ten minutes.
Blair Waldorf likes him. He’s sure that she likes him, at least a little bit, because Dan’s knows that there are a lot of underground, off-the-radar bars closer to her that serve better whiskey, that have better lighting for reading, that don’t smell quite as much like old ashtrays and cheap beer. Another B. WALDORF fact for his list:
Maybe doesn’t hate Daniel Humphrey entirely.
The rest, he’s pretty sure, will come with time.
“My coworkers are starting to talk, you know.”
“Well, send them my congratulations. First words are an exciting milestone.”
She flips a page. Breakfast of Champions today. “I’m aware.”
“They think you’re in love with me.”
“How cute. Tell me, Humphrey, are these coworkers imaginary? Because somehow you’re the only person I ever see working here.”
“Because you only come on the days when I’m working. Which brings me back to my point—”
“Your ridiculous conspiracy theories are distracting me from my reading. Don’t you have a job to do?”
He looks around the otherwise empty bar, the streets quiet on the other side of the windows. “No-pe. No one else seems to come here on Tuesday afternoons. Really, the only reason someone could possibly have to be here at this time of day is if they had a cru—”
“Every time you open your mouth I’m deducting another ten percent from your tip.”
His jaw snaps shut.
From behind the pages of her book he catches her smiling.
“How long until the wedding?” he asks on her eighth Tuesday, when she’s abandoned The Master and Margarita for her drink and casual conversation.
“One week, three days and twenty-two minutes,” she says, and sighs when Dan raises an eyebrow in half-astonishment, half-admiration. “Serena makes me keep a countdown on her phone. She says it’s more dramatic that way, but I’m almost positive that she’s worried she’ll forget otherwise.”
He scoffs. “Wow. What a catch.”
“She is.” Blair sounds serious, more serious than he thinks he’s ever heard her, and that’s saying something since the majority of the time she sounds as though she seriously wants to dig her perfectly manicured nails into his face. “She really is. If the two of us walked into this bar together right now you’d probably be so distracted by the skyscrapers that she calls legs that you’d forget I even existed. Believe me, it wouldn’t be the first time.”
There’s fondness in her voice. There is, but Dan likes to think that he knows her well enough to identify that there’s insecurity too, cautious vulnerability coating her words. He feels as though she’s testing the waters, seeing how far she can open up before she pushes him to the edge and causes him to abandon ship entirely. It almost hurts him to witness but even so it’s moments like this where he likes her the most, where she’s Blair instead of the rich girl who makes a point to insult his every move.
(Although really, he likes her any way. Dan’s big enough to admit to that now—he likes her when she’s drinking expensive whiskey, when she’s insulting everything he cares about, when she’s drunkenly quoting Austen to him in a horrible British accent and making him promise he won’t post it on Tiktok, whatever that is.
He just…fuck it, he likes her, and high school Dan would probably make fun of him for it but high school Dan was an idiot anyways.)
“The two of you walked into the bar together the first night you came here,” he reminds her, “and I saw more of her than I ever wanted to,” way, way more, “but I definitely noticed you first. Not just because you slammed your card on my bar, either.”
“Slammed my card on your bar. How scandalous.”
“Only if you want it to be.”
“Do you want to come to a wedding, Humphrey?”
It takes him a minute—a minute of Dan staring at her, a minute of Blair grinning like a cat with a canary clenched in its teeth—for him to realize that she’s not joking, that she’s actually inviting him to a wedding that takes place in less than two weeks despite the fact that the majority of attendees no doubt make his years’ salary in less than a day.
And the way she’s looking at him…the way she’s looking at him is more serious than he’s ever seen her look, despite the smile on her face and the mirth in her eyes. She’s actually asking.
“You’re out of your mind.”
“Please. As if you have anything better to do.”
“Do you?” she challenges, eyebrow raised, and he knows that he’s caught. His weekend plans as of late typically involve him sitting on the couch re-reading one of the well-work books on his shelves and wondering what Blair is doing, which is exactly as pathetic as it sounds. “Come on Humphrey, bringing an unknown Brooklynite as my date would be the perfect thing to drive that absolute Basshole insane.”
He’s going to say yes. Obviously he’s going to say yes, but Dan still plans on drawing the whole thing out a bit longer. “You keep saying Basshole as if you expect me to have any idea what it means.”
“It means exactly what it sounds like it means.”
“Isn’t it generally frowned upon to add a plus-on onto your invitation less than two weeks before the day?”
“Do you even know me at all? I marked down a plus-one the second I got the invitation.” He doesn’t flinch, and she stares him down for another moment before deflating slightly. “I don’t want to go alone, Dan. Please.”
That…that stops him in his tracks.
It’s the first time she’s ever said his name. His actual name. He likes the way it rolls off her tongue, short and sweet, and he likes the way she’s looking at him like she really does want him to say yes. He likes her, Blair Waldorf, a ridiculous combination of wealth and privilege and wit and kindness, and she’s asking him to step into the belly of the beast for her. An Upper East Side wedding is the last place that Dan Humphrey would ever want to be caught, but for her—
“You owe me,” he says, trying not to smile when her expression flashes from pouting to delight in less than a second. “I am a way better friend than you deserve, Waldorf.”
She snorts. “Please. We’re not friends, Humphrey.”
“You’re taking me to a wedding with you.”
“For convenience alone.”
“You spend every Tuesday night at my bar.”
“I told you, it’s to avoid the prying eyes of my adoring public. Don’t let it go to your head.”
“Admit it, you like me.”
They stare at each other, Dan and Blair, two entities separated by wealth and the wooden counter of a bar—and she laughs, just a little bit, just enough to let him know that he’s at least won this much. She may never admit to it out loud, but Blair Waldorf likes Dan Humphrey. That more than makes up for the pain of attending a rich person wedding.
“Give me your address,” she says, sliding her phone across the countertop towards him. “I’ll be sending an Armani suit and my tailor your way. Bringing a Brooklynite is one thing, but I won’t attend with someone who isn’t impeccably dressed.”
“I wouldn’t expect anything less.”
He gives her his phone number along with his address and they text every day after that—stupid things, things like Dan’s opinions on the Shirley Jackson he’s currently reading and Blair’s impassioned feelings for distain towards people who dog-ear the pages of their books.
They are friends. They’re more than friends. He’s sure of it, and he’s sure that she feels it too. He’s pretty positive that Blair wouldn’t send someone a rant-text about Madame Bovary at three in the morning on a Sunday if they weren’t something more than an acquaintance, if they weren’t someone that she was spending ungodly hours thinking about.
He tries not to read too much into it, but…well, admittedly he doesn’t do a very good job.
Blair Waldorf, crawling under his skin from the moment she stepped foot in the bar. Dan would be lying if he said he hadn’t seen this coming all along.
The ceremony is, admittedly, not what he expected. It’s short and succinct, led by someone named Carter who says things that Dan is pretty sure aren’t appropriate for a formal setting and the vows are full of innuendos and inside jokes, but he doesn’t feel all-too out of place. That might be because Blair, from her spot at the front of the room, keeps sneaking glances at him—she rolls her eyes or she grins or she laughs, laughs like they have some sort of secret, laughs like it’s for Dan and Dan alone.
Someone else is looking at him, too; the best man glaring with narrowed eyes, jaw clenched, but he’s not particularly bothered. He’s pretty sure that he understands what the word Basshole means now, and he’s pretty sure that he understands why Blair had been so hesitant to come to this thing alone. Chuck Bass seems like the epitome of everything he’s been raised to hate, and the thought of Blair and him together…he’d rather not dwell on it for too long.
Still, Dan doesn’t particularly care.
(He can’t, because she’d pounded on his door that morning in a golden dress that barely brushes her thighs and that Dan is pretty sure costs more than his apartment, and she’d looked him up and down and he’d known—he knows that look.
“You don’t clean up too bad after all, Humphrey. Who’d have known?”
“Don’t like, Waldorf. You’ve definitely fantasized about me in a suit at least once.”
“I plead the fifth.”
“You,” he begins, but stops in his tracks—the words you look beautiful don’t seem to encompass it at all, because she’s not beautiful. She’s incandescent. She’s glowing. She’s talked about how people always overlook her for Serena, how people always ignore her for the tall blonde with the wide smile, but for the life of him Dan can’t understand how that could be true. He can’t understand how anyone could want to look at everything other than her. “Wow. I don’t really know what to say.”
“Alert the presses. The great Daniel Humphrey, speechless? I never thought I’d live to see the day.” she says, but she blushes the prettiest pink that he’s ever seen and he wants to know how far down her chest the colour goes. “Stop gawking and get in the car, Brooklyn. I’m about to take you to the longest day of your life.”)
It’s a nice ceremony, he thinks. He can’t be sure. The people around him seem to think so, and he doesn’t know enough about high society weddings to disagree.
Blair smiles at him again, and—
The reception, however, is something different entirely.
It’s popping champagne bottles that probably cost more than a year of Dan’s rent and flashing lights with blasting music, although he doesn’t really know what else he should have expected. The older people at the wedding look moderately horrified but somewhat affectionate, small smiles gracing their lips that he’s sure are both unintentional and entirely genuine, and he looks at the happy couple dancing in the center of the room and—
Okay, he gets it.
Nate and Serena are nice. Nate gives him a bro-hug, two pats on the back, when Blair introduces them and immediately starts making plans for the two of them to hang out post-honeymoon; Serena wraps him up in a hug so tight he think he might suffocate, a nearly six-foot whirlwind of blonde hair and wine breath, and it’s only a little bit awkward.
“I don’t know what you’ve done to my best friend,” she whispers, and he’s almost certain he’s about to get a shovel talk before she continues, “but oh my God, promise me that you won’t stop. I’ve never seen her like this.”
Serena laughs, loud and bright, nothing at all like the silent shake of Blair’s shoulders. “Don’t act like you don’t know.”
Blair catches his gaze over Serena’s shoulder and rolls her eyes, playfully annoyed, and everything feels like it fits.
They spend the majority of the night like that: orbiting around one another, making quiet quips about the people she introduces him to (“The one who officiated? Carter Baizen. Don’t get too close to him; I don’t want his slime to stain your suit.”). Chuck Bass is ever-present but deliberately ignored, even as his voice seems to overpower all the music and echo across the room. Blair doesn’t acknowledge him and Dan follows Blair’s lead—it helps that her indifference doesn’t even seem to be intentional. There’s no tension in her spine or no forced cheerfulness to her tone, and when he drags her to the dance floor during the first actual slow song of the night she follows only a little bit unwillingly, complaining with affection in her tone that she doesn’t know how people from Brooklyn dance but if he embarrasses her she’ll bludgeon him to death with her Louboutins.
She rests his head on his shoulder. His hand flexes where it rests on her hip.
“This isn’t that bad,” he says, words muffled a little by her hair.
“It’s passable. You’d be thrown out of a cotillion, but clearly Nate and Serena’s standards aren’t quite so high.”
“I didn’t mean the dancing, but it’s good to know I’ve got the Waldorf seal of adequacy.” She laughs, only a little, and Dan feels a strange sense of pride at that. Every one of Blair’s laughs feels like a victory. “I meant the wedding. You made it sound like you were going to be dragging me into a warzone.”
“This is the Upper East Side equivalent of a warzone, Humphrey. Did you see Georgina’s dress? The she-devil wore white.”
“I know. You’ve pointed it out about fifteen times.”
“And the only reason I was able to stop the day from turning into World War Serena was by—”
“Spilling a glass of merlot on it to make her look like a knock-off Jackson Pollock.”
“Aw, Humphrey! You really do listen.”
“To you?” he starts, and Dan knows that he could make this into a joke. He knows that he could deflect, keep their relationship a safe combination between combative and flirtatious, but it’s half-past midnight and he’s had just enough Dom Perignon to loosen his once deliberately-tightened lips. “Blair, I love listening to you. God knows how considering the nightmare you were the first time we met—”
“Excuse me, but I’ve never been anything another than a complete delight.”
“And how you’re always interrupting me,” he continues, pulling back to grin at her just a bit, “but you’ve become one of my favourite sounds.”
It’s as if everything stands still: the music, the party, Blair, glancing up at him with eyes so large they should be anatomically impossible and a vulnerability that he’s never seen on her before. He wants to kiss her but he doesn’t want to kiss her for the first time in a place like this, on a crowded dance floor with her best friend and her ex-boyfriend and her other ex-boyfriend watching on. Not with her mother and step-father in the same room. Not like this.
But she’s still looking at him, much more sober than he, and Dan knows: this is the moment. If he lets this pass—if he lets Blair Waldorf leave this wedding without telling her exactly how he feels, he’s pretty sure that he’ll have lost his moment forever.
(And Dan is tired of waiting. He’s tired of being more Hamlet than Romeo, which, okay, neither of them are exactly aspirational, but he’d rather be a bleeding-heart romantic than an impotent hero who couldn’t make a move.)
“Do you want to get out of here?” he asks, and hates himself a little bit for how completely slimy the words sound. If Blair thinks as much she doesn’t let on; she just smiles, soft and sweet, and he knows he’s said the right thing. Somehow.
“I’ve been waiting for you to ask me that from the moment we arrived, Dan.”
“I like it when you call me Dan.”
“Dan,” she says again, eyes twinkling. “Oh, Dan! Have we discovered a kink?” And, okay—
Okay, fuck it.
Because he might be an uneducated, unrefined Brooklyn idiot, and he might not have attended a prep school with uniforms and he might not have any fucking idea who a van der Woodsen is and why they seem to be so important—but Dan isn’t entirely obtuse and Dan knows when a girl wants to be kissed, when a girl doesn’t care about their audience and doesn’t care about the optics of making out with a poor bartender in front of everyone she knows.
And Dan knows Blair, knows the flush on her cheeks and the freckles that dot the bridge of her nose like constellations. He knows that she never does anything she doesn’t want to do and that she never says anything that she doesn’t mean; he knows that if she’s looking at him like that it means that she wants him. He knows her like he knows himself.
And when she gasps against his lips, high-pitched and sweet, and lets out a breathless giggle almost perfectly in time with the music that sends a shiver down his spine—
Well, he knows that he’s made the right choice.
(Later that night, twisted under satin sheets at an hour so ungodly that Dan’s pretty sure he’ll have to sleep for ten days straight to recover from, Blair mutters an admission into his neck.
“I didn’t keep coming back to the bar because it was a good place to read,” she says, and it’s so ridiculous that he doesn’t bother even trying to suppress the laugh that escapes.
“You don’t say.”
“I kept coming back because I wanted to talk to you.”
“Blair, I know. I’ve been telling you that I know for weeks.”
“You’ve cast a weird, Brooklyn voodoo spell on me.” she mutters, snuggling in a little closer—Dan’s never been a cuddler, but he’s pretty sure that she might convert him. “I would sue you for emotional damages if I didn’t know how poor you are. There’s nothing there worth taking.”
“Your romantic sentiment is duly noted.”
“I like you, Humphrey,” she says, whispered like it’s a secret, and Dan figures that he ca teasing her about it for now. When she’s sounding this vulnerable, this genuine, none of his regular jokes feel like they would be that funny. “I really like you. How did this happen?”
“Brooklyn voodoo,” he repeats, and he kisses the smile right off of her face.)
She storms into his bar every Tuesday and Thursday, a whirlwind of Chanel perfume and perfectly coiffed curls, and eventually she meets his coworkers—definitely not imaginary, Dan points out, and she rolls her eyes in affectionate annoyance—and he thinks about the list, the one that keeps growing, the one that he’s pretty sure is never going to stop.
B. WALDORF, a five-foot-two unsolvable puzzle, sitting cross-legged in front of him with Margaret Atwood on the counter and her hand gripping his across the bar.
And yeah, he thinks.
He’s pretty okay with this.