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When Humphrey Met Waldorf

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“Come on, B. Please . I miss you and I’m sure Chuck can’t wait to see you. You weren’t here for Thanksgiving pie. Don’t tell me I have to miss out on Christmas Eve hot chocolate, too.”

Blair sighs, shifting her weight and reluctantly dropping her Vuitton onto the shiny white tiles of Chicago O’Hare’s international terminal.

“Hot chocolate? You’re going to have to do better than that to talk me into this, S. I don’t do coach . What makes you think I’d ever agree to a road trip?”

Serena’s exasperated huff is loud enough for Blair to hear over the phone.

“And if I were to agree to this it would at least have to be a town car with a driver—not some stranger in an unreliable jalopy .

“For the last time, B, he’s not a stranger. He’s Rufus’s son.”

“I don’t acknowledge a man with a dog’s name as an acquaintance,” Blair says, her irritation rising. But it’s not enough to eclipse her desperation.

Though she won’t admit it, she misses Serena, too. And it’s Christmas with Chuck that tempted her home from Paris in the first place. A part of her wishes that Chuck was the voice on the line, that he was the one moving heaven and earth to get her home for the holidays. She’d tried calling him when the plane landed, her flight unexpectedly diverted to Chicago due to the massive blizzard darkening the skies over New York. Like so many other calls she’d made since she left for Paris the month before, Chuck let it go to voicemail. Blair refuses to read anything into that, much like she refuses to acknowledge the growing rift between them.

She tells herself her eagerness to get home to Chuck is well-intentioned instead of suspicious. She isn’t lonely. She certainly isn’t worried about their relationship.

Regardless, with flights grounded for at least the next twenty-four hours, the truth is that Blair will have no choice but to take a car if she wants to make it to Manhattan for Christmas Eve the next day. Even she has to admit that finding a hired driver to take her the full day’s journey from Chicago to New York the day before Christmas Eve would be difficult under the best of circumstances. In an airport filled with hundreds of people in the same predicament, it’ll be next to impossible.

Blair ,” Serena scolds, but she can hear the suppressed laughter in her voice. “You know who Rufus is. My mom’s old friend?”

“Lily’s old boy friend, you mean,” she corrects. Blair does know him. She’s seen him around Lily’s pristine apartment for brunch, utterly out of place with his worn leather jackets and perpetually mussed hair. 

The ill-begotten Brooklynite offspring of Rufus Humphrey doesn’t exactly match the description of Blair’s ideal travel companion. And if Rufus’s other child, Jenny, is anything to go by, Blair doubts she’s going to get along very well with Rufus’s son. Jenny Humphrey was a persistent thorn in Blair’s side all throughout her senior year of Constance, and she doesn’t relish the idea of spending any amount of time with another Humphrey. But she’s out of options and out of energy to argue with Serena.

She takes a breath, scanning the over-crowded airport full of harried travelers, frantic families, crying babies.

“Fine,” she relents. “But if this guy murders me I’m going to haunt you worse than that haircut you got freshman year.”

Blair regrets her decision the moment Dan Humphrey’s old, white car comes to a puttering stop at the curb before her. It looks clean enough, well-maintained. If she’s honest it looks a bit like something out of a Hepburn film, which might be endearing if she weren’t about to ride eight-hundred miles into a snowstorm in the passenger seat. The thing’s got to be older than her mother, and the choking fumes coming from the tailpipe are anything but reassuring.

“I’m not riding in this death trap,” she announces without preamble when the aforementioned Humphrey exits the car to greet her.

He’s taller than she expected, but his look is otherwise very reminiscent of Rufus. Dark wool coat over flannel, close-fitting jeans that have seen better days. Their threadbare look is the kind that comes from years of wear, not the artfully ragged aesthetic she’d find in a shop window on Fifth Avenue. His dark hair is just a touch too long, an unruly curl hanging almost low enough to obscure his right eye.

“Nice to meet you, too,” he deadpans, withdrawing the hand he’d held out to shake. “And this car is perfectly safe. It’s a collector’s item.”

Blair arches a dubious brow. “You don’t look like the classic car collecting type.”

“What kind of type do I look like, then?”

She considers him for a moment, head tilted to the side.

“Pseudo-intellectual, down-on-his-luck barista.”

She expects him to bristle at that the way everyone else does when she gives them a dressing down. Instead, his lips tilt into a bemused smirk.

“Close enough. Are you always this friendly or did I catch you on a good day?” He doesn’t wait for an answer, just stoops down and starts gathering her bags.

Blair manages to resist the impulse to tell him to be more careful, that the Italian leather carry-on he’s slinging around like a sack of potatoes costs more than a month of his rent. Instead, she adjusts her purse where it dangles from her arm and taps her foot impatiently.

“I’m Dan, by the way,” he offers, voice straining on the last word as he hoists her luggage into the tiny trunk.

“Blair Waldorf.”

She walks around to the passenger side, heels clicking on the concrete, and nearly runs into Dan when he unexpectedly steps in to open the door for her.

“Um, thanks,” she mutters, folding herself carefully into the small seat.

The car is uncomfortably cramped. It smells like old leather and exhaust. It’s a considerable step down from the first-class seat on her plane over from France.

But when Dan slides in next to her she manages to bite back the complaints on the tip of her tongue. She’s going to need a lot more patience if she wants to survive the next thirteen hours this way.





For the most part Dan Humphrey’s company is slightly less unbearable than Blair had anticipated.

Conversation flows smoothly enough. Regular pleasantries and new acquaintance sort of questions. Dan’s doing all the asking, Blair providing clipped answers.

She’s never been a girl anyone would describe as quiet, but she’s got a Grace Kelly biography in her purse that she barely got to dig into on the flight, and she certainly isn’t interested in thirteen hours’ worth of small talk with a forgettable nobody from Brooklyn who she’ll probably never see again.

Dan either doesn’t notice that she’s being short with him, or he doesn’t mind.

He tells her the car belonged to Rufus. There’s a story about how he traded a guitar for it. Blair doesn’t really believe it but doesn’t care enough to question it, either.

“How do you know my dad, anyway?”

“I don’t really know him,” she says with a shrug. “I do know your sister, Jenny, unfortunately for me. And I’ve met your dad a few times at Lily’s.”

Dan pauses, his face tensing up peculiarly. He looks like he wants to say something to that but for the first time since they’ve left the airport, he falls silent.

This is the opportunity for peace and quiet that Blair has been waiting for. She fishes the paperback out of her purse eagerly, opening up to the part she’d left off on. Grace Kelly is about to marry Prince Rainier, about to become the Princess of Monaco. 

She tries to focus on the words and makes it successfully through about five pages before she realizes she isn’t really reading it, just poring over the lines distractedly, her eyes passing over the same paragraph half a dozen times. Dan’s brooding silence is deafening.

She closes the book with a sigh.

“Okay, Humphrey, what is it?”

His fingers tighten on the wheel until his knuckles go white.

“Nothing,” he says finally.

Blair narrows her eyes at him curiously but doesn’t press the issue.

“Fine. It’s not like I care .”

A noncommittal hmph from Dan is barely audible over whatever indie nonsense he’s got playing in the car.

Blair glances down at her book again, then back to Dan. It’s the first time she’s really taken a good look at his face. He needs a shave—and a haircut for that matter. But the line of his jaw is pronounced in a not unappealing way. His face in profile isn’t handsome. Definitely not. But he’s not un attractive. His eyes are brown, a shade even darker than her own. Sad eyes. Not that it makes any difference to her, of course. Humphrey’s feelings matter about as much to Blair as the spring offerings at Old Navy. But somehow the prospect of sitting under the pall of his gloominess for the rest of the day is even worse than his inane babbling from before, and it’s not like it would kill her to make conversation.

She settles on the first question that comes to mind.

“What is this God-awful noise you’ve got coming from the speakers in here?”

He gives her a sideways glance, evidently surprised by her attempt to engage.

“It’s Bright Eyes.” He says it like it’s obvious, as if Blair would ever have had a reason to be exposed to his eccentric hipster drivel before this moment.

“Well, it’s terrible.”

“Conor Oberst is a lyrical genius,” he counters. “Let me guess, you’d rather something like Taylor Swift or Beyoncé?”

“Ugh.” She rolls her eyes, moving to tuck the shoulder strap of the seatbelt behind her back so she can turn in her seat to face him properly. “First of all, there’s nothing wrong with Taylor Swift or Beyoncé. They’re feminist voices of our generation. And hating things that other people like isn’t a substitute for a personality, Humphrey.”

He scoffs, but that same sort of smirk from when they’d met on the sidewalk that morning is slowly returning to his face.

“And if you must know, no. They wouldn’t be my first choice to replace your whiney, emo banjo music.”

“Then what would?”

“Well that depends. Maybe something classic like Sinatra or Billie Holiday.”

Dan nods thoughtfully. “Fair enough, but I don’t think that’s good road trip music.”

“Maybe not to you . If you insist on something more contemporary, then I guess I’d say Lana del Rey, Sara Bareilles, Amy Winehouse. Maybe Coldplay or Thom Yorke.”

You like Radiohead?”

Blair gives him a tight-lipped smile. “Not anymore, if it means having something in common with you .”

“Maybe you’ve got some taste after all, Waldorf.”

“Please. I don’t think the man wearing store brand polyester is in any position to comment on taste.”

Dan laughs, his ill humor vanishing by degrees. He isn’t wounded by Blair’s admittedly derisive sense of humor the way so many others are. There’s something freeing about that.

Chuck still hasn’t returned her call, but she doesn’t even notice, doesn’t even check her phone when she stores the Grace Kelly book back in her purse.





A few hundred miles and several bathroom stops later—always at a nice restaurant or store because Blair would quite literally choose a squat in the trees along the interstate before being compelled into a gas station restroom—and the sun has nearly set.

The time has passed almost unremarked and Blair isn’t completely miserable. Despite some heated disagreements over whether it was worth it to drive five miles out of the way to use the restroom in a Dillards instead of the Circle K at exit 57, she and Dan are getting on about as well as can be expected.


“You’re wrong,” she’s saying her arms crossed stubbornly.

“I'm not wrong!” Dan insists. “He wants…” he trails off, pausing to check his rearview before pulling onto an exit ramp. Blair hasn’t eaten since the croissant and mimosa she had on the plane and she’s hungry enough to agree with Dan’s suggestion that they stop at some roadside cafe.

“You're wrong,” she repeats.

“He wants her to leave because he loves her. That's why he puts her on the plane.”

“But I don't think she wants to stay.”

“What? Of course she wants to stay. Wouldn't you rather be with Humphrey Bogart than the other guy?”

“I don't want to spend the rest of my life in Casablanca married to a man who runs a bar. I suppose you think that’s snobbish, but it’s not. It’s rational.”

“You'd rather be in a passionless marriage?”

“And be the first lady of Czechoslovakia,” Blair says primly.

Dan slows as they approach a diner—“Mel’s Diner,” if the blinking neon sign with the “N” burnt out is any indication. She flashes him a you-can’t-be-serious sort of glare, but he pretends he doesn’t see her.

“So Czechoslovakia over the love of your life,” he says in a tone of genuine disbelief. “Just because he owns a bar and that’s all he does.” He throws the car into park and turns to look at Blair expectantly.

Yes.” She flips the fold-up mirror down to check her appearance, reapplying her lip gloss with a smack of her lips. “Any woman in her right mind would do the same. Women are very practical—even Ingrid Bergman—which is why she gets on the plane at the end of the movie.”

The cold when she climbs out of the car is shocking enough to make Blair miss her cramped but cozy seat. She hurries to the diner entrance as fast as she can trot around in five-inch heels. It must not be very fast because Dan overtakes her in time to get the door for her. Again. This whole gentlemanly bit is catching her a little off guard. She expects it from men like Nate, honed to mannerly perfection in private school and stuffy society etiquette classes. For them, it’s habitual, impersonal, as natural as walking down the street. She doubts Dan had any such upbringing.

The little diner has some Christmas lights up along the windows and the counter in honor of the holiday. A harried-looking waitress leads them to a booth in the back corner and Blair stamps down the urge to demand a table further away from the kitchen doors. It’s a diner, she reminds herself. Not Butter.

Dan sits down across from her and orders a black coffee without looking at the menu.

She follows suit. “I’ll have an espresso doppio and a bottle of San Pellegrino with a glass on the side. No ice, please.”

She can hear Dan stifle his laughter into something like a snort.

“What?” she wonders aloud. The waitress is staring at her like she’d ordered in Latin.

“We’ll just take a pot of coffee for the table. And a water for my friend here.”

“We are not friends, Humphrey,” Blair hisses when the waitress is out of earshot. “And if you think I’m going to drink Folger’s and tap water then you’re in for a rude awakening.”

“You’ll live,” Dan says simply.

And she does. The coffee is bitter and weak, but drinkable. Dan talks her into joining him in ordering “breakfast for dinner,” and despite the waitress’s visible irritation when Blair asks if the waffles are Belgian and the orange juice fresh-squeezed, their meals arrive without incident.

“Anyway, I get it now,” Dan says, munching thoughtfully on a piece of bacon.

“Get what?”

“What you said. About Casablanca .”

“Oh?” She carves off another piece of her very underwhelming waffle. An entire day without a real meal is the only possible explanation for how much of it she’s eaten.

“Yeah. You would get on the plane because you’ve never really been in love.”

“Excuse me?”

“Ilsa and Rick had a great love. If you’ve never had a love like that then you’d probably think Laszlo was the right choice in the end.”

Blair slams her fork down on her syrupy plate, perhaps a little too forcefully, as the resulting clang rings throughout the restaurant.

“I’m in a great love. Right now.”

“Is that so?”


Dan leans forward, resting his forearms on the table.

“Who is it?”

“Chuck Bass,” Blair announces, her nose tilted haughtily upward.

“Hm. If this Mr. Bass was as wonderful as you’re saying then you wouldn’t be here with me. Your family’s loaded, right? I’m sure anyone rich enough to date Blair Waldorf could charter a helicopter or something to bring her home in her time of need. At least, that’s what I’d do for someone I loved.”

Her hands ball into fists in her lap under the table.

“First of all, I am so not with you.” Blair makes a face at him like she’s gagging. “And I – I’ll have you know that Chuck offered to send me his helicopter, but the winds are too high from the blizzard. It wouldn’t have been safe.”

Blair has told enough lies to know that this isn’t one of her best.

Dan can clearly see right through it. He levels her with that smirk again. She wants to smack it off his face, but he raises his hands in surrender.






Back on the road, Blair makes the unfortunate discovery that Dan’s car’s heater “takes about an hour to warm back up if it’s been off for a while.”

“I’m going to k-kill you,” she vows through chattering teeth. The leather seat is icy on the backs of her thighs, clad only in tights, her skirt too short to really offer any warmth or cover to her legs. When she’d gotten dressed in Paris that morning it had been a decidedly fairer day.

It’s like the inside of the car is somehow even worse than the frigid December night outside. Blair swears she can see her breath steaming in the air.

She can also see Dan, eyeing her with mounting concern in her periphery. But she refuses to look at him. She isn’t sure how many more indignities she can endure in one day.

“Here,” he offers, hunching forward against the steering wheel and shrugging awkwardly out of his coat.

Blair’s own coat is couture, beautiful, a black Chanel with subtle blue embroidery that matches her stockings, but it’s cropped at the waist and not nearly thick enough.

Still, she isn’t tempted by Dan’s offer of the rumpled, grey wool disaster, no matter how thick and warm it looks. She’d sooner freeze than wear Dan Humphrey’s cheap and most likely smelly coat.

“Ew,” she says immediately, swatting him away. “No thanks.”

He takes a deep breath, shaking his head at her faintly.

“Suit yourself.”

The car warms up slowly. Not enough to be comfortable, but enough for Blair to stop shivering violently.

To Dan’s credit he attempts to distract her with conversation despite her snitty attitude and rapidly declining mood.

“Where were you coming from?” he asks after a period of uncomfortable quiet. “When your flight got diverted to Chicago.”


“Paris? Wow. And you chose to come back here for Christmas? Why?”

To see Chuck , she thinks but doesn’t say.

“I was just there to visit my father. He has plans with his husband’s family for Christmas so I came home to be with my mom.”

“Your parents are divorced.”

It isn’t a question, but Blair answers. “For the past few years, yes.”

“I’m sorry.”

“I don’t need your pity, Humphrey.”

“Course you don’t.”

“What about you?” she asks. “Why were you there?”

“In Chicago? I wasn’t really there. I was just passing through. On my way home from Iowa when my dad called and asked me to pick you up.”

“Iowa?” Blair snorts. “God, Humphrey, I knew you weren’t exactly high society, but I didn’t expect you to live in a corn field.”

“Not a corn field. The Iowa Writers’ Workshop.”

Oh. She hadn’t expected that . The University of Iowa had one of the best if not the best writing program in the country. She turned to glance over at Dan, a little impressed in spite of herself.

“Like Flannery O’Connor.”

“Yeah,” Dan laughs. “I’m just like Flannery O’Connor.”

“So you’re heading home for the holiday, then?”

“Ah, no. Not exactly. This trip is going to be a little more permanent.”

He jabs his thumb over his shoulder, pointing into the backseat.

Blair follows the movement to see a couple duffle bags, a pillow, a stack of records and a musty looking cardboard box with the word “books” lettered messily on its side in black marker. Nothing else, and the back seat is stuffed to the ceiling.

“Moving back to New York,” he adds.

“Yeah, I gathered that.”

It occurs to Blair that she’s got more bags from one trip to Paris than Dan Humphrey needs to pack up his entire life.

“Since this is the part where one would usually brag about their accolades, I take it that you didn’t actually graduate?”

“How perceptive,” he deadpans. “No, I didn’t. I’m the stereotypical dropout and parental disappointment.”

Blair shrugs. “I didn’t finish at Columbia. I’ve got bigger plans.”

You went to Columbia?”

“Uh, yeah,” Blair confirms, narrowing her eyes at him. “Don’t act so surprised.”

“Well, I am.”


“I don’t know,” he says carefully. “You just don’t strike me as a Columbia girl.”

“Well, I’m more of a Yale girl,” she agrees. “But it ended up working out better to stay in the city.”

“That’s not what I mean either.” Dan searches for the words, turning to look at her before continuing. “You just don’t really strike me as a college girl.”

“I don’t understand.”

He gestures to her vaguely: Chanel coat, matching Louboutins.

“I just feel like girls like you don’t really go to college to get what they want. You could practically buy the world, marry someone rich. You know what I mean.”

The worst thing is that Blair does know what he means. Serena turned down Brown, after all. And why wouldn’t she? She had enough combined Van Der Woodsen-Bass millions to party her way around the world. And that was exactly what she had been doing since high school.

But Blair always thought of herself as different from Serena, and not just because of Serena’s long legs and blue eyes and perfect hair. Serena was the wild one, unfocused, and if Blair was honest, sort of uncultured. Serena is the kind of girl Dan is describing. But Blair has spent the past few years doing everything in her power to be something different, something better. To rise to meet Chuck’s level of success and stand on her own merit. The fact that only one day in her presence is enough to tell Dan that she’s as privileged and shallow as ever confirms her worst fears about herself.

She can’t think of anything to say, so doesn’t say anything; just stares straight ahead through the windshield, watching the dark road rushing up to meet them. All those years of carefully cultivating her best fake smiles to lie her way through Constance and earn her Queen B status still aren’t enough to hide the hurt from her face.

Dan is immediately remorseful.

“Wait, Blair, I’m sorry. I didn’t –”

“Yes, you did. You meant it, and you’re probably right,” she snaps. “But it’s not like any of this matters. We aren’t friends, and I can’t overstate how little I value the opinion of some impoverished, dropout, failed writer from Brooklyn.”

This time even Dan has nothing to say.

Blair angles her body toward the door and scoots to the far edge of the seat, as far away from him as she can manage. She’s being childish but she doesn’t care. She’s jetlagged, lonely and frankly sad, and she’s tired of having to feel all these things in the presence of Dan Humphrey. She fiddles around in her purse to find her phone. Still no call from Chuck.

Resting her face against the cold glass of the window, she gazes up at the stars. They’re far enough out from the city that the sky is still relatively clear. Still a couple hours to go. She doesn’t really trust Dan enough to willingly fall asleep in the car with him, and she knows that it’s rude to leave a driver alone to keep themselves awake during long trips at night. But the one cup of weak coffee isn’t enough to combat all the forces weighing on her heart as well as her eyelids, and before long she falls into a fitful sleep.





Blair wakes up when the car stops moving.

She blinks her eyes open blearily, trying to penetrate the fog of confusion that accompanies waking from a deep slumber. She’s stiff all over and her right foot is asleep from being tucked up under her in the seat. When she stretches her arms out behind her the motion shifts Dan’s coat down into her lap . He must have draped it over her while she slept. There’s something mortifying about that, regardless of how warm and cozy she is now compared to the shivering misery that preceded her nap. The idea that she’s been sitting there unconscious for hours next to him is just disconcerting. What if she’d been snoring, or worse, drooling ?

Dan’s eyes swivel over to her when he notices that she’s woken up. His face brightens into a small, hesitantly apologetic smile. Blair just stares at him, her mouth set in a hard line.

Looking out the window she can see they’re in bumper-to-bumper traffic, the climate outside the car completely changed. Everything is blanketed in white. The wind—which is strong enough to howl almost as loud as Dan’s shitty music—is whipping snow flurries against the car at a constant rate. Visibility is so bad their headlights hardly illuminate anything beyond the car in front of them. She’s suddenly incredibly grateful that she never learned to drive. She wouldn’t want to have to take a shift at the wheel in a storm like this.

For his part, Dan looks calm and unbothered by the ferocious weather.

“Uh, we’re a little behind schedule,” he observes. “Because of the storm.”


“But we’re about an hour out of Manhattan. You can put your address in the GPS.” He gestures to his phone where it’s mounted on the dash.  

“Why would I give you my address, Humphrey?”

He sighs, scrubbing a hand over his face in frustration.

“So I can circle back and kidnap you tonight.”

When she doesn’t laugh his face falls a little. “Just put it in, Blair. Unless you’d rather direct me there yourself.”

She rolls her eyes and grabs the phone roughly. Her freshly French-manicured nails tap audibly as she types.

And then there isn’t anything left to say. If Blair thought the silence was awkward before, it’s ten times worse now. She decides to pretend she’s fallen back asleep so Dan doesn’t make some mad attempt to pave things over.

Chancing the tiniest peek to the left to make sure he isn’t looking, Blair lifts his coat back to cover herself as she snuggles up against the door. The fabric is softer than she expected, and it turns out the only thing it smells like is laundry detergent and the faintest hint of some spicy cologne.

After a while the tension drains itself out of her limbs as she sits there with her eyes closed. Driving through the snowy night stewing in her own melancholy sets a better mood for Dan’s pretentious lonely boy ballads, and she finds that she doesn’t mind the music quite as much.

When they pull up at the curb outside her apartment Blair is just comfortable enough to dread venturing out into the snow. She feigns sleep for a little longer, listening to the slam of the door as Dan gets out, the creak of the trunk flipping open.

She’s startled when he comes around and opens the passenger door, the blast of cold from outside making her squeal in alarm.

Blair glares up at him.

“Rise and shine,” he says with a cheerfulness that isn’t at all reflected in his face. If it’s possible Dan looks even more exhausted than she is. The storm has let up some, but the snow is still falling and there are flakes accumulated in his hair already from the short time he spent unloading her bags.

When she takes his proffered hand to help her to her feet, his skin is surprisingly warm on hers. To Blair’s horror, there’s a little flutter in her chest at the contact.

She drops his hand like she’s been burned and shoves his coat against his chest abruptly.

“Look, Blair,” he begins, “I really am sorry about earlier –”

She raises a hand up to stop him.

“If you want, I can help you bring these up,” he offers, pointing to the neat little cluster of her bags beside the car.

“Absolutely not. Give it up, okay? It’s not like we could ever have been friends anyway. You’re Brooklyn and I’m Upper East Side. Different worlds.”

She’s already turning her back to him, stepping onto the curb and getting ready to dial Dorota to come and help with her bags.

“That’s a shame,” he says from behind her. “You’re pretty much the only person I know in New York these days.”

Blair allows herself one, perfunctory glance back.

“You’ll live.”

He chuckles. “Merry Christmas, Waldorf. Have a nice life.”

Waiting for Dorota she stands out on the curb, hugging herself for warmth and watching Dan’s taillights shrink as the car advances down the street.

“You, too, Humphrey.”