A/N: This is just sort of a little holiday fic that I thought of and decided to start it. It's different than most of my stories because I have it completely planned out from beginning to end, so it should all be posted within the next couple days. Very AU, most connections are explained in the story- but basically none of these people went to the same high school (aside from Nate and Blair). I wouldn't recommend reading if you can't stomach Derena smut. The characterizations are slightly different from the show, but they should be generally identifiable. Also I've always wanted to write a fic that swaps some of DB's lines, so this has some of that. They're all about 24-25 years old. It's a lot of dialogue. I like dialogue I guess.
*Ultimately a DB fic, but warning that there's quite a bit of Derena involved (just a much darker twist on Dan/Serena)
I swear I could write a whole novel of just author notes explaining my own stories.
ENJOY and happy holidays!
"What are you looking at, Waldorf?"
"Your hair. You look like a muppet."
Epperly clears her throat loudly, calling their attention back to the meeting. Blair smiles politely. Dan rolls his eyes.
"As I was saying," Epperly continues, "I'd recommend getting your pieces to me as soon as possible. Everybody forgets during the holidays. Dan, you'll be writing about what women should give men for Valentine's Day."
"I'm starting to feel like I'm being singled out as the only straight guy in the office."
"For some reason, women find your cynical attitude entertaining even when it comes to giving advice," Epperly says dryly.
Blair laughs quietly, shaking her head as she scribbles a few notes down. Dan narrows his eyes at her.
"Blair," Epperly skims through her list and Blair snaps into focus, "I want you to rethink pinks and reds. Give the classic colors more dimension."
Blair nods briskly and writes more quickly. Dan can't help but smile. She's such a suck up that sometimes it nauseates him, and yet it's only because she has passion and conviction about her job. Dan wishes he could say the same for himself.
"Finally, we have an interview with Duchess Kate as the feature story. We need our best writer on this one," Epperly's eyes move from Dan to Blair. "I'll let you two duke it out and get back to me."
Everyone clears out of the conference room and Dan follows Blair to her desk, watching the way her black trench dress swings over her thighs. She drops her notes and turns to face him. Immediately, she shakes her head.
"No," Blair says sternly, "I know what you're thinking. The answer is no."
"Waldorf, your prose is shit. Let me have this one. I need this story if I want a shot at getting promoted to junior editor."
Blair purses her lips. "Kate Middleton is one of my idols and style icons. I can connect with her on a level you would never be able to. It's not my fault you don't give a shit about this magazine."
Dan throws a finger against her mouth to hush her, stepping closer. "I do give a shit about this magazine. I don't give a shit about what color shoes men find most attractive on women. I need to be taken seriously as a writer."
"You don't take anything at W seriously!" Blair whispers loudly, "You barely meet your deadlines because you're out fucking whatsherface while her husband's away on business."
"Can we not go there right now?" He lowers his voice and Blair smirks. "Fine. You can have the Middleton piece, but I need you to do something for me."
Blair takes the opportunity to sit down at her desk and leans back in her chair, interested in his proposal. Dan drops a thin stack of paper in her lap.
"It's a short story I just finished. I think it'd be great in the February issue."
She flips through it carefully and lets out a sigh. She's not looking forward to spending her night reading Dan Humphrey fiction and formulating a pitch to submit to Epperly and Stefano.
"This isn't Cosmopolitan, Humphrey. We don't need some pathetic love story at the end of the issue."
"Would you stop?" Dan leans over her desk, licking his lips. "It's a romance set in the Prohibition era. I even incorporated fashion into it."
Blair uses her heel to shove him away from her desk gently. He grabs her ankle and smiles, dropping it to the ground.
"I'll see what I can do."
xo
They met freshman year at NYU. Dan was infatuated with Blair's psychotic roommate, Georgina, and Blair was still in a serious relationship with her high school sweetheart, Chuck Bass. Georgina was always flakey and Dan would end up sitting in their dorm for hours talking to Blair while waiting for her to get home.
Chuck was too busy with Bass Industries to ever visit Blair at school, so she enjoyed having someone down to earth hanging around all the time.
They debated foreign cinema, impressionists, and various poets.
When Georgina lost her mind and dropped out, Dan found himself stopping by the room anyway, simply out of habit.
Sometimes they'd sit on the couch, Blair's feet in his lap, and he'd read Paulo Neruda's love sonnets to her. They never considered the romantic sentiment of this.
Chuck dumped Blair two days before New Years Eve, so Dan agreed to be her date to a mutual friend's party. She felt a bit pathetic, tagging along on Dan's arm as they said hi to everyone and denied any rumor of a relationship.
"I'm gonna grab us some drinks," Dan yelled over the music and Blair nodded as he made his way to the bar. After catching up with a few people, Dan checked his watch to see it was already minutes before midnight. He glanced over his shoulder but couldn't see Blair anywhere.
She was standing in center of the ballroom when the countdown began. Music was blaring and people were yelling and part of her wished she had just stayed home, curled up in her bed with a glass of wine.
"5-4-3-2-1"
Screams erupted around Blair and she looked up at the confetti fluttering over the room and champagne showering her hair. Moments after the countdown ended, an arm hooked around her waist and a pair of lips crashed into hers. She squeezed her eyes shut as she kissed him back and every thought of Chuck and loneliness left her mind.
Dan released Blair slowly and she smiled back at him dazedly. Dan grinned, kissing her again gently.
"Happy New Year, Waldorf."
xo
After work, Dan takes a cab to the Upper West Side, climbing the stairs to Serena and Carter's flat. He knocks loudly and waits over fifteen minutes for her to answer. Serena was always making him wait. It doesn't help that Dan's sure there are security cameras in the hallway, watching his every move.
Dan met Serena in late March at a W photo shoot, a little over a year after her marriage to Carter Baizen. They connected almost immediately and he had never met anyone so carefree and spontaneous. She had dragged him into the dressing room after her photo shoot had tanked because she was too drunk.
Serena opens the door and yanks him inside, smashing her lips against his. His pants are off before they even make it to the couch. Dan pulls her dress over her head and shoves her back on the leather, climbing up her body. She pushes his shoulders back down her stomach and bucks her hips gently.
Dan knows what she wants.
As soon as his nose grazes her center, Serena lets out a soft sigh. Her legs fall open in his arms. Her tan skin glistens in the sunlight and Dan lets his hands slide over her thighs. He runs his tongue along her folds, flicking over her clit a few times before inserting one finger slowly and following it with his tongue, letting his thumb circle her clit quickly. Another finger and he continues his movements, reveling in the sounds coming out of her mouth.
Serena lets out an airy laugh that turns into a loud moan as she comes, gripping the couch tightly. She sighs, gripping his hair to keep his head in place.
"More," she gasps.
Serena wants more and Dan will give it to her. Dan is pathetically in love with a blonde ray of sunshine who wears another man's ring on her finger.
xo
Blair sits at the bar, sipping her sloe gin fizz and glances over her shoulder when she hears Nate approaching. He flashes her a set of white teeth and Blair smiles back, straightening her spine as he takes a seat next to her.
"Hey, I can't stay long. I have to meet my dad's communication director to talk about the press conference tomorrow."
"I'll make this quick then," Blair finishes her drink and drops Dan's short story on the bar. "Do you still have your connections at The New Yorker?"
Nate flips through the packet, letting out the same sigh Blair had earlier in the day.
"I don't think I can get this published, Blair."
"I got Epperly to include your expose on the Bush sisters last July and nobody gave a fuck about them anymore. You owe me."
He laughs and takes a gulp of his scotch.
"Why do you care so much about this story anyway? You didn't even write it."
"It means a lot to Dan."
Nate and Blair had been friends since high school and somehow never lost touch. As the son of a senator, Nate was always out partying with other political offspring. Blair wasn't certain if he ever did anything other than that. She had received more than one drunk message asking her to come make out like they did in high school. Blair could never get herself to climb out of bed for him.
"Maybe if you cut down the length," he reasons, sliding the story back to her. "You're always running errands for that guy, Blair. Should I be jealous?"
Blair's brow furrows as she shoves the papers into her bag and glances up at him, shaking her head in confusion. She reaches for Nate's glass, but he pulls it out of her grasp.
"Blair, do you…do you like him?"
"What?" she laughs nervously, fingers playing with her waves. "No, no, no. I don't- I don't like him. I mean he does-" She swallows. "He does smell nice."
Nate's eyes widen. "You want to bang Humphrey!"
Blair's hand flies over his mouth and she narrows her eyes. When she moves her hand away, Nate smiles.
"Unless you have already…"
Blair ignores his question and orders another drink.
xo
Throughout college, Dan and Blair skated around each other. Bumping into each other at parties, or sharing notes in class. They both dated a few people, but no one met the other person's standards. Blair twisted Dan's arm into breaking up with every girlfriend he had in college, and she somehow listened to Dan's insistence about her poor choices in men.
They got each other through finals, sharing lingering silences outside of the library, playing footsie under the table as they studied. There was always a tension that they couldn't manage to break.
Graduation came around and Blair's mother had a fashion show in Paris to attend.
"Take enough pictures so I can feel like I'm there!" She exclaimed over the phone, models and designers yelling in the background.
Blair was disappointed, but not entirely broken up about it. She and her mom weren't close enough for Blair to even notice the absence. But hearing that Dan's dad wouldn't be making it to town had moved something in her. She knew his dad had some addiction problems, but it was always assumed he'd be at graduation. When he received his diploma, he had looked into the crowd and Blair made sure to meet his eyes before he walked off the stage.
After the ceremony, everyone was saying their goodbyes and Dan pushed through the crowd to get to Blair.
"We did it," she smiled.
"We did."
As everyone tossed their caps in the air, Dan pulled Blair against him and kissed her, his tongue fighting to gain access to her mouth. Blair gasped as she parted her lips and wrapped her arms around his neck to pull him down for more.
"Ahem."
They broke apart to find two women staring at them with raised eyebrows. One was pretty, middle aged. The other, elderly with glasses sliding down her face.
"Mom," Dan said, and Blair could see the earnest smile on his face as he embraced his mother. She couldn't remember the last time she hugged her mom. Dan kissed his grandma's cheek and then his mom moved closer, touching his arm gently.
"He really wanted to be here," she said softy and Dan nodded, not wanting to say anymore about it.
"Are you going to introduce us to your girlfriend?" his grandma asked loudly.
Dan laughed and placed his hand on the small of Blair's back, urging her forward.
"Blair, this is my mom, Alison. And my grandma, Joan. This is Blair Waldorf."
"Will Blair Waldorf be joining us for your celebration dinner?" Alison asked, shaking Blair's hand gently. She was really quite beautiful when Blair got a closer look. She wondered what his dad must look like.
"I wouldn't want to intrude. You probably want to catch up."
Dan furrowed his brow and placed his hand on Blair's shoulder gently. "You should come."
So she did.
It had been years since Blair had had a family dinner and it was nice to be around people that clearly cared about each other over anything else in their lives. She answered a few questions about her mother's Waldorf Designs, along with her plans for the future, but for the most part the focus stayed on Dan.
"We're so proud of you," Alison said and Dan's cheeks flushed lightly. "You graduated from a good school, you've got a bright future, a beautiful girlfriend. It's everything your dad and I always wanted for you."
Dan nodded and his hand moved to Blair's knee, squeezing it gently. She glanced up and he was smiling back at her. It all seemed so genuine, she wondered what this meant for them. What would happen after dinner when his family had left and they didn't need to put on a show anymore?
Dan's fingers traced up Blair's leg slowly and she bit her lip to keep in a gasp.
"Is your food okay, dear?" Joan asked from across the table. Blair nodded with a smile as Dan's hand slid further up her thigh. She barely contained her moan when his knuckles grazed her center. She looked over to find him chuckling to himself.
After they said their goodbyes to Alison and Joan, Dan's hands never left Blair's body. Even as they waved to the leaving car, his fingers were intertwined in her hair, his body grazing hers gently from behind.
"My mom likes you," he said against her ear when the car was gone.
"Is that supposed to set the mood, Humphrey?"
Dan laughed as he flagged down a cab. "I guess not."
The car came to a stop in front of them and Dan opened Blair's door, affectionately watching her climb in.
She slid into the backseat and grabbed for Dan's shirt, pulling him on top of her. She could feel him hard against her thigh and let out a soft moan.
"Where are we headed?" The driver asked, trying to ignore the scene occurring in the backseat.
Blair spit out her address before Dan's lips were on hers, a hand sliding up her dress. His finger hooked on her underwear, pulling them down slowly.
"Jesus, Blair," He whispered as his hand grazed over her center. "You're so wet."
He moved the ridges of his fingers against her clit and she moaned into his neck. "Shut up, Humphrey."
The car came to a stop outside of Blair's building and he helped her out of the car. When they got into the elevator, Blair slammed him into the wall, her hand snaking into his waistband. His eyes fell shut as he felt Blair's fingers graze him gently, a soft groan escaping him. The elevator doors opened and they stumbled into the foyer, collapsing on the stairs in a heap of limbs. He hiked up Blair's dress as she fumbled with his belt, pushing his pants down hastily.
They never made it up the stairs.
Dan held her waist tightly as he thrusted into Blair. Her head fell back as she moaned, wrapping her legs around him to pull him closer.
"I've thought about this so many times," he mumbled against her neck, moving faster.
Her breath hitched. "Me too."
Blair's fingers reached down to circle her clit, but Dan batted her hand away, applying pressure with his thumb. Her back arched as his body moved against hers. He propped one of her legs up on his arm to let him go deeper and Blair felt her stomach drop in pleasure.
"Dan," she moaned softly, digging her nails into his shoulders. She let out soft airy breaths as she came, her body shuddering. Dan followed shortly after, collapsing next to her on the steps. They both struggled to catch their breath before pulling their clothing back on.
They stood in the foyer, facing each other, and Dan smoothed Blair's hair down gently.
"So where do we go from here?" He asked softly.
"I can't," Blair cleared her throat, standing straighter. "I can't have a relationship right now. I need to focus on my career."
Dan nodded slowly, his thumb grazed her shoulder. "Right. Me too. Maybe we should just…"
"Stick to being friends," She agreed.
"Well," Dan stuck his hand out to her. "It was nice being your boyfriend for a couple hours."
Blair smiled and nodded stoically as she took his hand. "You played the part well."
Within a month Blair was working at W, and when Dan applied for a job a year later, Blair gave him a shining recommendation to write human interest pieces.
Sometimes she still wonders if things would've been different, had she been honest with him.
And herself.
xo
Serena shoves Dan onto his back, the hardwood cold against his hot skin. Her mouth glides over his length gently and Dan's breath hitches as he grabs a handful of blonde hair to pull her up his body.
She settles on top of him and as Serena's hips start to roll, Dan's eyes roll back.
"I love you," he groans out, gripping her waist. He shuts his eyes to memorize her rhythm, her head falling back as she rides him.
"Shhhh," her hand rests on his chest. "Don't ruin it."
As Serena's pace increases, Dan can feel pressure building and he sucks in a breath to stop himself but it all feels out of his control.
"Not yet, baby." Her movements slow and Dan feels tortured, bucking his own hips to make her move faster again. Serena works to hit the right spot before rocking against him, her breaths becoming stilted. Dan's hands search for anything in reach as he grasps for control.
Serena moans, her hair falling over his chest like a curtain, "Right there," she says breathily, more to herself than anyone else. Dan watches her come undone on top of him, his eyes hazy as he finds his own release inside her.
"I'm gonna miss that in Barcelona," she pants, climbing off of his lap.
Dan pulls his briefs back on and sits up.
"What? I didn't think you were actually going."
Serena laughs as she pours a drink, taking a long sip. "Of course I am. He's my husband. We have a life together."
"We do too," Dan says, really quite pathetically. "Sort of."
"We have fun, Dan. I'm still married."
An overwhelming sadness washes over him. Serena kills the loneliness that rests deep inside of him when he leaves work to return to an empty loft, or stands at the bar by himself during a W party. She spins through his life like a never ending hurricane and he knows he should take shelter, but instead he stands in the middle of the street like an idiot.
"You should get going soon," Serena says, scratching his head affectionately. "Carter will be home soon."
Sometimes Serena watches her neighbor's great dane. It gives her something to do when she's not modeling, because she gets bored easily just sitting at home. She likes the dog. She likes playing with it and taking it for walks. Serena would never want the dog as her own. She enjoys bringing it back its own apartment at the end of the day. Serena likes the dog, but she doesn't like it that much.
Dan pulls his clothes on and slams the door when he leaves.
xo
Dan shows up to Blair's place around 11 pm. She yawns deeply before grabbing her glass of red wine and padding down the stairs to the foyer.
"What are you doing here?"
Dan lets out a sigh and she can see the pain in his eyes. "You're the only person I can have a furtive, emotionally-loaded conversation with right now."
She nods to the living room and Dan follows, taking a seat on the couch. Blair sits next to him and places her glass on the coffee table. He buries his head in his hands, exhaling deeply.
"What the hell am I doing, Blair?"
She rubs his back gently, moving closer on the couch.
"I'm writing a fucking how-to column for a fashion magazine. My dad can't get sober to save his life. My sister is running a successful dress business in London and never calls. I haven't talked to my mom since graduation, and Serena is moving to Barcelona with Carter."
"Dan," Blair says softly, lifting his chin to meet her eyes. "Aside from your dad, those are all things you can change. You can get a different job. You can call your mom, and your sister. And Serena… well, maybe it's for the best she's leaving."
"I just- I can't…" he trails off and Blair can smell the scotch on his breath.
"What do you really want?"
"To be happy," he says, his voice coarse. "But I don't think I know how to anymore."
