Disclaimer: I own nothing

A/N- Kind of a mix between Gossip Girl and Romeo and Juliet. Totally AU, but some things stay the same. It's not completely to the plot of R&J either though.

Quick little character comparison

Chuck: Romeo Carter- Tybalt

Ben: Benvolio Dan- a Montague

Vanessa- a Montague Bart Bass - The Montague

Blair: Juliet Nate - Paris

Harold Waldorf- The Capulet Dorota- Nurse

Serena- A Capulet...I guess. Mrs. Queller- The Prince

Kati Farkas- Rosalind ?????- Mercutio

Ch.1

There had always been brawling between the two groups of residents in the Upper East Side. Old Money and New Money. Serving as the leading force behind the Bluebloods was Harold Waldorf, a formidable opponent to his self-made enemy, Bartholomew Bass. However, the contents of this tale are not about these men. Rather, this is a story of their children, a pair of star cross'd lovers.

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"Look, there goes Archibald and his Abercrombie Clones," scoffed Dan Humphrey to his long-time best friend, Vanessa Abrams as they sat on the steps outside St. Jude's during lunch break, "they're probably headed off to get some botox and a blow out."

Vanessa laughed as Dan smiled. Even amongst his fellow "New Moneys" he felt like an outcast. His dad, Rufus Humphrey had made it big with his music career. Lincoln Hawk was a legend. Even with his current art gallery venture, Rufus had managed to rake in the money.

Yet, Vanessa and Dan only seemed to have each other, the lone artistic souls in the Upper East Side. They were grouped with the New Moneys at school and accepted because of their wealth, but they were never popular...never the leaders.

One of Nate's close friends, Carter Baizen turned at the sounds of laughter and saw Vanessa and Dan looking at him.

"Are you laughing?" he shouted, his tone clipped and superiour. He raised his chin in defiance as his friends gathered around behind him.

"Yes," Vanessa called back, "isn't it kind of obvious?"

Carter sneered, his eyes darkening, "Are you laughing at us?" he rephrased.

Vanessa leaned over to Dan.

"Is it against school rules if I say yes?" she whispered, her voice dripping with sarcasm.

Dan laughed again, "It is if we start a fight."

She faced Carter again.

"No, of course not," she answered sweetly, "Now, scurry off. I don't want you to be late for your appointment at the nail salon."

A few of the New Moneys saw the tension brewing between the students and made their ways over to have Dan and V's backs.

Carter took a step forward and opened his mouth to return an insult, but was interrupted by the loud ringing of the bell, signaling the end of lunch. He narrowed his eyes menacingly, while Nate attempted to calm him down by putting a gentle hand on his shoulder. He brushed Nate off with a scowl.

"Prepare for utter social destruction," he snarled, before turning around and leaving with his cronies. Nate looked back, his eyes seemingly regretful, before continuing with his friends.

Vanessa and Dan waited until they were out of sight before exploding with laughter.

"Social destruction?" she scoffed, "who talks like that?"

Dan smirked, "what does that even mean?"

One of the onlookers rolled his eyes, it was a boy with sandy blonde hair...Ben Adamson...Chuck Bass' stepbrother.

"It means," he replied smartly, "a Gossip Girl showdown...they're going to try and get as much dirt as they can on any of us and destroy our reputations."

Vanessa and Dan choked on their laughter once more.

"Gossip Girl Showdown?" Dan mouthed at V.

The boy looked affronted at their laughter.

"Laugh now," he told him, "but in a few weeks, when no one will speak to you, when no college will accept you, when even your own parents will be ashamed to look at you, don't say I didn't warn you."

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The students involved in the lunch time confrontation were called to the Headmistress's office almost immediately.

Dan looked around her office, seated with him were Vanessa, Ben, Carter, Nate, and some other Old Moneys.

"It has come to my attention," Mrs. Queller began in her dignified tone, "that all of you have been making the students of Constance Billard and St. Jude's uncomfortable with your constant arguments."

She stepped away from her desk, but not before Dan noticed her close a website on her computer...a website that looked suspiciously like Gossip Girl.

"This most recent dispute, resulting in the threat of social destruction is the latest of these annoyances. If any of you make any other overt efforts to antagonize each other or cause unrest in your respective schools again, be aware that this will result in your immediate expulsion."

All the students stood up and began protesting the harsh potential punishment, but Mrs. Queller silenced them with a wave of her hand.

"I don't want to hear it, your parents are on their way to come get all of you."

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"This is ridiculous!" Ben Adamson ranted as he stepped into Bad Bart's limo, "I wasn't even involved!"

Bart rolled his eyes, "you're right, this is ridiculous. I have to miss an important meeting to pick my stepson up from school where I hear he's been causing trouble with the Old Moneys...again. I'd expect this kind of behaviour from Chuck...but not from you."

Ben snarled, "I told you - I wasn't even part of the stupid fight!"

Bart looked at him for a moment before turning back to his business papers.

"I believe you...you've always been too rational for such things...if only Chuck could learn a little from you," Bart sighed, "where is Chuck anyways?"

"Probably at Victrola, he's been keen on getting you to invest in it so he's been working on a portfolio for the past few weeks...but he's been in an odd mood since that Kiss on the Lips party," Ben replied honestly, smiling at Bart's previous compliment.

"I noticed," Bart replied, his eyes not leaving his papers, "perhaps you can talk to him...figure out what's wrong."

"I can do my best."

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Chuck stretched across a small loveseat at the front of Victrola, surrounded by dancers, desperate for his attention and money. He sighed in frustration.

"Chuck, dear brother!" a voice cried out from behind him.

Chuck smirked, turning to face his step-brother, "Oh, I think you're mistaken. I'm the son of Bart Bass...you're the son of a money-grubbing whore and god knows who else.

Ben chuckled, "Oh Chuck, charming as ever."

Chuck leaned back in his seat, "I try."

"Even still," Ben sat down beside him, "your wit seems a little off...ever since that party you've been...less sharp."

Chuck rolled his eyes, running a hand through his dark hair.

"It's Kati Farkas...she's one of the hottest new girls at Constance, and I almost fucked her at the Kiss on the Lips party...but she heard someone call my name and she realized that I'm New Money...I need to tap that ass, you know seal the deal before I can fully enjoy fucking someone else."

"You do realize that you're seriously disturbed," Ben commented, "but if you're that concerned about it, you do realize the perfect opportunity to seal the deal would be at the Masquerade Ball tomorrow night, right?"

Chuck sat up suddenly in his seat, "you're absolutely right...with the masks no one knows who's who."

Ben sighed, "that's the idea," he said impatiently.

Chuck simply sneered before getting up and heading to leave.

"Where are you going?"

Chuck continued, not looking back, "I need a costume to perfectly disguise myself."

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"Blaaiiirrrrr," Serena van der Woodsen whined, "do we have to get so fancy for the stupid masquerade?"

"Of course!" Blair scoffed, scandalized at Serena's attitude, "besides, Nate will be there and since my mother had dinner with his parents, she's been dropping hints like crazy that he's been planning our future. I need to look perfect for him."

Serena smiled at Blair's wishful attitude, "well, good luck with that."

Blair narrowed her eyes, "thanks!" she replied sweetly.

Serena giggled as she held another dress up to herself in the mirror.

Blair, however, sat down on the bed, her eyes downcast, "Nate seems distracted now...even more so than after..you know..."

Serena looked down, ashamed.

"I just have no idea why...I've been trying to do everything right, I just don't know what else I can try." Blair flopped back onto the bed.

"Maybe you need to move on, find someone other than Nate...atleast for now," Serena suggested.

Blair shot up, "never!"

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Chuck fastened his mask around his face as his limo came to a stop outside the Maquerade hall.

"I don't even recognize you," Ben commented as their chauffeur opened the door.

"That's the idea," Chuck mimicked Ben's earlier words.

"Well, what if you don't recognize her either?" Ben questioned.

"Please," Chuck scoffed, "these sluts focus more on their dresses and hair than any sort of disguise."

"If you're sure," Ben sighed, following Chuck out of the limo and into the party.

Chuck's eyes scanned the room for Kati Farkas before stopping on a group of three girls.

There she is

He began heading over but stopped dead as one of the girls with Farkas turned around. His mouthed opened slightly as he took in the beauty. She wasn't hot like Kati...she was stunning, gorgeous, the perfect female specimen. Suddenly, Farkas was banished from his mind...he wanted this mystery girl, whoever she was...atleast some girl made an effort to wear a decent costume.

He waited until she left her friends, appearing as though she was looking for something...or someone.

"I couldn't help but notice that a beautiful girl like you shouldn't be wandering around alone at a ball, come dance," he approached her smoothly, expecting her to fall into his arms like all the others.

"Sorry," she smirked, "I'm waiting for my boyfriend...he's getting clues to find me, so I can give him a prize."

Chuck sighed, of course she'd have a boyfriend.

"Well, you look ravishing," he added, "if I was your man, I wouldn't need clues to find you."

She looked him up and down before replying.

"Or ravish me I'm sure."

Chuck wasn't ready to give up on this girl, her biting wit so comparable to his own.

"Well, if your boyfriend is a no show...drop him and come check out Victrola tomorrow night, it's a-"

She interrupted him, "a strip joint."

He ignored her, "a burlesque club. A respectable place to relax, let loose. It's pure escape."

He noticed the corners of her mouth turn up almost into a smile before she seemed to see someone behind him. He turned to see who it was, scanning the crowds for a few moments. Chuck turned back to ask her what she was looking at, but she was already gone.

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Everyone was looking at the clock as it neared midnight. Almost time to remove the masks.

10

9

8

7

6

Chuck looked around the room for the mystery girl from before.

5

4

He spotted her looking around, probably for her idiot boyfriend.

3

2

Her eyes seemed to spot Chuck instead, apparently she wanted to know who he was too.

1

In a flurry of colour and quick movements everyone's mask was torn off and tossed into the sky, like a graduation of sorts. As the glittery masks twirled to the floor Chuck saw the mystery girl appearing once again. His stomach dropped before he started to laugh.

Blair Waldorf? The Queen of Old Money...the daughter of his father's only enemy...the long time girlfriend of Nathanial Archibald...that's who he was hitting on?

Her face seemed to fall as recognition dawned in her expression...everyone knew Chuck Bass...leader of New Moneys with a bad reputation. She seemed mortified for even indulging him in a brief conversation.

Chuck's suprise quickly faded away as he took in her appearance. He'd always seen her as a loathsome individual, the epitome of everything he hated about the Old Moneys. But after their brief interaction...after seeing her with the mask on and deeming her the most beautiful girl he had ever encountered...he knew he couldn't lie to himself. She was perfection. But she was also a Waldorf. Her name alone forbade him from approaching her ever again.

He saw Nate suddenly run up behind her, grabbing her hand...obviously apologizing for not finding her in time. She ripped her hand out of his and stormed away as he followed, apologizing profusely. Her eyes seemed to soften at his words. She shook her head but still seemed to forgive him, as her eyes wandered over his shoulder and met with his.

She was perfect. So why was she a Waldorf?

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