Character Breakdown

Blair Waldorf – An aspiring writer from Brooklyn going to Constance on a scholarship. Nicknamed 'Lonely B' by GG. Currently 'outside' of the UES circle.

Daniel Humphrey – Son of the Wall Street Tycoon, Richard Humphrey. More interested in classic literature than he is in following his father's footsteps, but won't admit it out loud. Dubbed 'Prince of the UES' due to his exuberant wealth and charm.

Serena Van Der Woodsen – Charismatic socialite and Queen Bee of Constance. Best friend and ex of Daniel Humphrey. Loathes Blair Waldorf. Nicknamed 'Queen S.'

Rise and shine, Upper East Siders. The days are shorter and the wind is colder, but even the harsh bite of winter can't keep Manhattan's elite from slipping out of their dens for their holiday themed lattes. As the snow falls and temperatures drop, some kings and queens retreat indoors for the holidays, but rest assured that yours truly refuses to let our royalty enjoy their hibernation for too long. 'Tis the season for giving, and I have no doubt we'll have all kinds of secrets to unwrap come Christmastime.

xoxo,

Gossip Girl

Blair rolled her eyes at the blog post on the popular gossip site. Was this really how the 'elite' occupied their spare time? As she scrolled further down the page, she was almost glad she didn't have any friends at Constance.

The brunette continued absentmindedly overlooking the website, twirling her dark hair through her fingers, before a picture caught her eye.

-Spotted: D and S catching up over coffee at their favorite little spot in Le Petit Mort Café. Friendly outing or nostalgic rekindling? Eighth time's the charm, right lovelies?-

Her eyes widened at the amateur snapshot of the couple and quickly examined the date of the post: Sunday 9:13 a.m. A knot formed in her stomach as she realized she had been at that same coffee shop mere minutes before she was there. Serena Van der Woodsen, the almighty Queen of the Upper East Side.

Initially, Blair had hoped to have an incident-free educational experience at the prestigious prep school. Blair wasn't ignorant; she knew she didn't belong. So she took to keeping her head down whenever she was at Constance. She even took special care to avoid upsetting the hierarchy. Still, it turned out that even existing around Serena seemed to rub her the wrong way.

Serena was unlike anyone she'd ever met, and not in a good way. It bewildered her that a guy like Daniel Humphrey could tolerate, much less enjoy the company of such a shallow, vain bitch.

Even if he presented an aloof persona, Dan didn't fool Blair for a minute. It was hard to pinpoint the moment she figured it out, but a notable memory she could recall was catching him alone at a reading for a local writer, utterly transfixed by the words being read aloud. She had watched from afar, but from that moment, Blair knew that there was something of substance to the trust fund kid, and she had silently admired him ever since.

Looking at the picture again, Blair caught sight of a first edition Great Expectations nestled firmly in Dan's grasp in the picture, and a faint smile grew on her lips. Funny, she had the same one. Obviously, he was a man of taste, and he had better things to read than Gossip Girl.

Realizing the dichotomy of her own thoughts, Blair quickly shut her laptop and scolded herself for even entertaining the notion of reading such a juvenile, distasteful blog. If Blair Waldorf was one thing, she was above the Upper East Side, even if she wasn't worthy enough to be a part of it.

Tapping her nails against the side of her cardboard cup cozy, Serena pursed her lips as she waited for Dan to take his seat across from her. This little excursion would no doubt result in a blast on Gossip Girl, and that was her intention.

Her mother had been less than approving of her antics lately, and if she thought Serena was getting back together with the one guy who could provide for her, then what Lily Van der Woodsen didn't know wouldn't hurt her.

Dan took a seat opposite Serena before setting his favorite Dickens book underneath his chair and rubbing his hands together. "I take it you and your mother aren't exactly getting along?" he remarked nonchalantly.

The blonde sitting across from him furrowed her brow and took a sip of her coffee. "What makes you think that?" she asked unconvincingly.

Dan exhaled and scratched at his head slightly while answering. "Oh, I dunno. You asked me to coffee, yet you've said three words to me in the past five minutes," he pointed to her shirt while cocking his head to the side, "Tsk. And you're wearing the same shirt you wore yesterday?" He gave her a lighthearted laugh, indicating that he didn't judge her. He had known Serena his entire life, and despite their ups and downs, he could read her like a book.

She crossed her arms across her chest, self-consciously drawing her coat over her recycled outfit from the night before. "I don't know what you're talking about," she replied with a huff.

"You know, you don't have to lie to me Serena. I mean, come on, it's me." He shrugged his shoulders as if he was nothing special, and Serena laughed in response.

"No, you're right. I know. I'm sorry, I just don't want you to think I'm using you to curb my mom's judgment." She extended her hand and placed it on top of his. "You understand, though, right?"

He set down his coffee at the touch of her hand. It wasn't an unfamiliar feeling, since the two had dated numerous times before, but he couldn't help but notice how cold her hand was. "Wait, your mom's judgment? I thought you just crashed at some random guy's place to avoid her."

A girl taking a picture on her camera phone from the outside window caught his attention, and it all came together. "Was this all to convince her that we're dating again?" Dan took his hand out of hers and placed it on his knee.

Serena looked down at the table and wrinkled her nose. "Kinda? Please don't be mad."

Dan shook his head. "No, you know what? I'm not doing this again," he said while standing up to leave.

"Aw come on, Dan. Wait," she pleaded, grabbing his hand. "You know it's not like that."

Again, he retracted his hand from her grasp. "But it is like that, Serena. We're supposed to be friends, but you still think you can use me to get out of a fight with your mom." She remained silent, unwilling to make eye contact with him. "Whatever. I'll see you later," Dan said before leaving a tip and heading for the door.

Rubbing her forehead with her fingers, Serena exhaled through her nose. Of course Dan was upset with her now, just like her own mother. At least the picture had been taken so the morning wasn't a complete waste.

She was about to get up when she saw a thick red book underneath Dan's chair. She glanced up to see how far he'd gotten, but Serena could only see the backside of his limo as it drove away.

Upon further inspection of the book, she could hardly believe her eyes. "Ew, Dickens." Why the hell was Dan carrying this around? Did he need extra credit? No way. He could easily pay someone smarter to take care of that for him.

So why did he have it?

Serena carefully opened the book and flipped through the pages to see if there was anything inside, and to her dismay, there was. Confusion distorted her features, and a jealous streak she didn't know she had began to grow tenfold. Calmly, she left the book on the table, in case he decided to come back for it. With a flip of her hair, Serena left and hailed a taxi.

"Where to, miss?" the driver asked once she was inside.

"Brooklyn," Serena answered. The two words written in neat, cursive script continued to burn themselves into her mind. Blair Waldorf. "Now, please."

Dan was halfway own the block when he realized he had forgotten the book. "Shit. I'm sorry, can we go back?" he lamented to the driver.

The Humphrey heir tapped his foot rhythmically against the interior carpeting of the limo as they made the journey back, his hands becoming clammier by the minute.

After what seemed like hours, the vehicle pulled up to the shop, and Dan wasted no time in getting out. Before entering, he quickly scanned the shop to make sure Serena had left. After deciding that the coast was clear, Dan entered the shop and glanced around the tables.

Much to his relief, the red book was waiting for him right where he left it. He swiped it up, and flipped through the pages as if to make sure the little notes and underlines hadn't been taken away or erased.

A small laugh escaped from him. He truthfully had no idea why he was so attached to this thing. It probably would've been easier to pick up a new copy later than to double back and retrieve this beat up, used one, but there was just something so arresting about it.

The commentary squeezed into the sides of the pages and the passages the previous owner chose to illuminate, these weren't annotations done for a school assignment.

No, definitely not. These came from someone who was invested in the story, who had a deep-rooted appreciation for the written word, someone like him.

More specifically, someone by the name of Blair Waldorf.

Dan was ripped from his daze when his phone vibrated in his pocket. He promptly pulled it out and opened the text message he received from his father. Need you here. Now. Dan pushed out a sigh as he made his way once more to the limo.