Work Header

The Heirs of the Frontier

Chapter Text

A shiny glint from the strap of his leather mahogany oxfords call for Dan’s attention on the rowdy bus. He steals quick glances around when he can, wondering if anyone from the crowd would be happening to stop in the Hamptons. Or is he just a sad soul too prideful to soak in the wealth from his stepmother.

Lily offered him the town car, but he is still new to the idea of having a butler, let alone a personal driver.

Unlike his rich spoiled friends, he has a summer job interning for the New Yorker. They enjoyed reading his work, yet both published short stories make him blush from embarrassment.

With his last name Humphrey, he imagines there will not be any edge or advantage in the college application process. Sacrificing his summer for the possibility of enrolling into an Ivy league school is a reality he is willing to accept.

He feels his phone vibrate and sees the name of his crush pop across the screen. It’s a picture along with a text underneath. The image is of his crush Blair Waldorf in her thin yellow polka dot knee length summer dress, laying on top of his bed in Cece’s home, offering a devilish smile that turns him on. He barley notices Serena smiling at him in the picture.

Blair: We’re waiting ;)

“So you’re best friends with Blair Waldorf and Serena Van Der Woodsen,” Vanessa interrupts his thoughts of Blair, sitting right next to him in the bus.

His childhood friend moved back to the city recently, much to his surprise. It was becoming tiresome being surrounded by only Manhattans’s Elite and he had missed her dearly. A fresh perspective on things is something Dan could use right now.

Blair and Serena are quite popular online, collecting a significant amount of money from the very little they post on social media. Most of its collaborative dancing, but he also figures videos and images of their lifestyle has something to do with their popularity as well. They’re entrepreneurs already, and Dan can’t help but consider he’s behind.

“Your friends are in the top 1% of the population, congratulations Dan,” Vanessa says, eyeing him strangely as his focus is instilled on his phone.

Dan can’t stop texting Blair. He misses her so much and is concerned he won’t help but scare her off from his want and neediness. All week he has been occupied. He made sure of it, hoping it would distract him from thinking about the fiery brunette taking a stake ownership over his heart.

Outside of volunteering, so he can later leverage those recommendations during his application process, he is also in a soccer league after work for two nights a week, sailing club two nights a week, and work every weekday. He's physically and mentally exhausted. Thankfully he gets off work at noon on Fridays and can arrive to the Hamptons in a reasonably time. The perks of the being the intern he supposes.

During his junior year, he didn’t receive many minutes on the soccer team, and this year he would enjoy playing with his other best friend Nate. Not to mention those activities will all look great on his application.

"When was the first time you met them anyway,” Vanessa inquires, taking another attempt in bringing him back to reality.

A startled Dan answers,”Oof, it's been a while… a lot has changed.”

“Tell me please, it’s better than watching you text,” Vanessa says wryly, narrowing her eyes at Dan.

A sigh escapes his lips. He was hoping to catch up on sleep during the bus ride over.




The summer sun beams directly on Dan's skin. His eyes swirl around, soaking in the freshly blossomed trees of Central Park. He marvels at how the sun makes everything sparkle. The past year has been quite lonely and painful for Dan. His family life is crumbling, and he has lost most of his friends since deciding to attend St. Judes.

After a friendless freshman year, Dan decides he doesn’t want to spend another summer bumming around his father’s loft in Brooklyn.

Blair Waldorf is holding a party at her penthouse in Manhattan, and fortunate for him she lives near his favorite place to visit, the grandest park of them all.

There is a doorman waiting outside her large building. He stares up, becoming overwhelmed by the height. She must have an amazing view of Central Park. A lump forms in his throat, as he swallows nervously and hands over the invitation to the doorman, who smiles and opens the door for him to enter.

The lobby is pristine and elegant, everything he imagined and more. Dan doesn’t think he has ever seen so much marble in his life. There is a young familiar couple entering the elevator, and he recognizes them, but is sure they have no idea who he is. He follows them in, knowing they are heading for the same floor. He offers them a smile, but the well kempt boy is still attempting to figure out who he is, or what his last name is. It’s all about the last name with these people.

When the elevator rings and stops, the doors slide open and he is immediately speechless. Never has he been to such a crowded party. The typical Humphrey family gatherings would be no more than 20 people, and they could easily hold it in their loft.

This on the other hand was well planned. As he sets foot into the foyer, he is able to notice how much thought went into each meticulous thing. Blair Waldorf lived up to her name. He had heard, but seeing it firsthand is a completely different experience.

He doesn’t quite know where to go, and it’s easy for him to get lost. Before he can set foot into the living room, he does hear excited giggles up the staircase. When his eyes set atop the staircase, he sees them. The two most beautiful girls he has ever laid his eyes upon. Serena Van Der Woodsen, and a wicked Blair Waldorf.

Knowing he technically wasn’t invited. Nelly Yuki was responsible for the invitations, and lucky for him, Nelly is nice to him for some reason. She gave him an invitation, but warned him to not run into Blair.

So he drifts away, into the crowd, and moves along, looking for someone to talk too, or something to do. Anything is better than being at home, where he is surrounded by yelling, depression, and drinking.

After snaking around, and watching others from afar, he eventually realizes he will have to make a move and join in on a conversation if he is interested in making friends. He’s been listening in on the conversations, and he finds them to be inconsequential. If they were to hear his opinion on things, he would come off as a giant ass. Nor would they be intellectually inept to keep up with him. A drooling Chuck Bass would be more entertaining for these people. 

He decides to slip out onto the terrace, in the hopes that it has a view of Central Park. That view itself would be worth crashing this party for. Dan has a roof in Brooklyn, but can’t say the sight is as appealing.

He perches himself on the wide stone railing, and leans his back against the brick and green ivy vines rolling along the building. Blair Waldorf’s penthouse apartment is gorgeous. He also couldn’t help but notice the paintings and classical music collections they owned. A family of class and good taste in art comes to his mind. He thinks Blair is a bully, but seeing her home sheds a different light and changes his perspective a little.

There is only one thing to do when having such a beautiful view before him. He lifts his joint to his lips, and sparks it, watching the sun slowly cascade away, and hint at the evening upon him.

"Do you smell skunk and laundry detergent?”

A startled Dan almost drops his joint, and looks over to see a wrinkled nose Blair glaring at him, with a tall sunny Serena standing beside her giggling.

“Who is this,” Serena asks, staring at him curiously.

“I don’t know.” Blair’s eyes narrow at him as they approach him. Then her eyes suddenly widen as it hits her. “Oh my god. This is the scholarship kid S.”

A crease forms in-tbetween Serena’s brow. “We have a scholarship program?”

Dan sticks his hand out to Serena immediately. “Dan by the way.” Serena smiles and takes in his hands, making Dan blush. His crush is touching him right now and he feels overwhelmed with giddiness. He then looks over to Blair. “I'm flattered you know me."

Her fists curl and press on her hips. ”You're the number one ranked student in our class, Nelly is second, and I'm third. Of course I know my competition.”

What an odd teenage girl he can't help but think. 

“You want some,” He offers Serena his lit joint.

“Thanks.” She nods with a smile and plops down on the stone with him.

A smile escapes his lips. He can’t help it. The girl of his dreams is sitting with him, smoking weed. She’s just as cool as he imagined.

Dan notices Blair quickly swipe her hand in to take his journal from him. “Hey, that’s my journal!”

She turns her back to him and starts reading, oblivious to his privacy. “You crashed my party without an invitation. I think it's only fair.” Blair opens it to read his scribblings. “Wow your handwriting is very feminine.”

Dan and Serena laugh. He can’t help it, she’s pretty funny.

“You just wrote this,” Blair then asks in surprise as a crease forms in-between her perfectly sculpted dark brows. “You think Serena and I are the prettiest girls in New York? Are you sure about that?”

“It wasn’t meant to be shared but this how I feel.” He swallows hard, taking in Blair’s intent stare.

He’s never had someone stare at him with such intense eyes. It makes him nervous. Maybe it’s because of how much easier it is to notice how beautiful she is.

“This is pretty good weed Dan,” Serena compliments, passing the joint over to Blair.

Blair scrunches her nose. “You call this a joint?”

He rolls his eyes. “I wasn’t expecting to share.”

A smirk spreads across her lips, and he feels his stomach drop. Her faces, they’ll be the death of him he thinks.

“You came to a party with this?” A sigh escapes the pretty brunette’s plump lips. “Wow you really are a virgin. You have much to learn.” She waggles his thin joint in his face. “What if you were to meet the girl of your dreams? You can’t ask her to come to the terrace and offer her this!”

“I think it’s cute.” Serena looks at Dan and giggles. “Your virginess I mean.”

Serena is as nice as advertised, but Blair isn’t the ice queen he expected. She will however call him out if he says something stupid. He loves that. She has a way of keeping him on top of his toes already.

From her pink clutch, matching her pink dress, Blair picks out her perfectly rolled pink joint. Dan wishes he could come up with something to pick at, but being the smoker that he is, he can offer nothing but respect.

“Oh I know!” Serena claps her hands in excitement. “Let’s shotgun it.”

Blair arches a perfectly sculpted brow, staring directly at him. “You think you can handle that Brooklyn?”

“How do you know so much about me,” Dan questions back, staring at her strangely. This girl is one of a kind for sure.

She rolls her eyes and takes a seat next to him, so that he is in-between both girls now. She hands the pink lighter and joint to Serena before letting her attention fall back into his journal, much to his internal dismay. There are so many embarrassing details in his journal.

“You’re a reader,” Blair notes and he thinks he catches a smile. “I read all the classics, and nothing resembles my relationship with my boyfriend Nate.”

Dan laughs, surprised by how much he enjoys her humor.

Serena takes his attention away by taking a hold of his jaw, and pressing her lips on his, before blowing the smoke in his mouth.

He blows the smoke and sees her smiling seductively at him.

“Wow,” Dan replies lamely. There is nothing like the allure of Serena.

“Who is Vanessa?”

Dan groans, annoyed that the brunette is ruining his super sexy moment with Serena. “She’s my ex.”

Blair pokes at him in the rib. “Wait you’re the one who hacked into our school?” She glares at him.

Dan rubs the back of his head nervously, embarrassed by her reading such personal things. “In my defense, I was attempting to impress her.”

Dan decides to tell them about Vanessa, the heart break, and how lonely this past year had been for him. Time flies and before he knows it, the moon is out, sparking against all of their skins.

It’s the best night Dan has ever had, but he will now remember to never put that in his journal.

“Wow how lame am I? Dan Humphrey had sex before me,” Blair says dryly, after he finishes the story. He can’t help but laugh and sees Blair curling her lips towards him.

“Wait Humphrey?” A surprised crease forms in-between her brows. “Is Rufus your dad? He comes over all the time.”

Dan’s heart drops to the floor. That can’t be right.

“What do you mean?”

He knows the tone in his voice changes, but he can’t help it.

Serena’s eyes soften. “You didn’t know?”

Dan abruptly stands up. “I have to go.”

He doesn’t wait to say goodbye, because the only thing on his mind is confronting father.

"It was nice chatting with you Stan,” Blair shouts.

Later that night, his sister would ask him who was cooler, Serena or Blair? He would have said Serena before the night, but now he couldn’t give his sister answer.




“She called you Stan,” Vanessa asks, attempting to suppress her laughter.

“She’s adorable.” Dan chuckles shaking his head. “A little evil, but harmless in the grand scheme of things.”