AN: I've tried writing a couple of times, but I typically get bored and uninspired. Chuck and Blair (as well as the rest of the nonjudgemental breakfast club) stole my heart the minute I began watching the show and well, I wanted to see if maybe I could muster up some creativity, write them my own story, and give them the ending that I believe they deserve. Reviews are most appreciated!

Plot Summary: Under the less than watchful eye of New York's most elite, growing up means Gucci before Gerber, champagne before bottles, and vanity and jealousy bred at a young age. Let's see what our little darlings grow up to be. Welcome to the Upper East Side.

Disclaimer: I do not own Gossip Girl, Chair, Bart Bass, or the lovely Upper East Side. Some story lines will be similar to those on the show, but others will be different.

Chapter 1:

When they were 6, he first noticed her, like really noticed her. It was her birthday party, a day filled with festive hats, loud music, and sugary cake that ended up mostly on their clothes instead of in their mouths. He noticed her curls, the way they bounced, the brown shiny hair swishing behind the petite girl as she dashed across the foyer, all giggles and smiles as he began to count. 1, 2, 3..

Charles Bass was in his finest jacket, a red and pink bow tie hanging lopsided on his neck as he peaked one eye open, skipping from 4 to 100. Behind him, he immediately heard a sneeze and turned around.

"Found you." He smirked.

His best friend seriously sucked at this game. The same age as Chuck, Nate Archibald was long limbs and thin shoulders, sandy hair and blue eyes, the complete opposite of his friend. Chuck, tiny for his age, had long brown hair that fell into hard, nearly black irises and pudgy hands with tiny, plump fingers. Nate rolled his eyes and muttered about the game being stupid before sitting down on base (the stairs.)

Not even a minute later, a pair of tiny heels was heard clinking from the second floor.

"I'm bored." A voice whined from above them.

Nate's head immediately shot up, eyes wide and a stupid grin plastered on his face. Chuck sighed and shoved his hands in his jean pockets, pout evident on his face. "So stop whining and play with us instead of playing with Blair's stuff upstairs." He snapped at the blonde who, by now, had reached the middle stair and was giving Nate a fluttering of her lashes. Serena van der Woodsen, the prettiest girl in Kindergarten, also known as Blair Waldorf's bestest friend, had a crush on everyone. Or, at least, that's what Chuck told all who asked. "And get my new dress dirty!" Serena returned her attention to Chuck and gestured down to the blue polka dotted dress that flared at her waist and hung down to her knees, a sweet bow hanging down the back. "Blair and I got matching ones." She informed the boys with a nod, as if this made the dress more special. "Hers is pink. Mama Waldorf made them and... " Chuck tuned her out.

Speaking of the birthday girl... he looked around and peered into the dining room, eyes scanning the table of adults in search for the small girl. Blair was tinier than he was. She could be anywhere. Mr. and Mrs. Waldorf were sitting close, hands linked loosely together on top of the table as Mrs. Van der Woodsen and whomever her new husband was laughed at whatever Eleanor was saying. His gaze fell on his father, who had an arm around his mother, the woman Chuck got his eyes and brown locks from, and quickly returned the stare with an icy blue glare of his own, the polite smile on his face quickly fading at the sight of his wandering son. He jutted his chin out, gesturing that the boy return to the party with the rest of the children. Chuck flushed and nodded, eyes on his tiny fingers as he scurried back down the hall in search of the birthday girl. He looked back and saw Nate and Serena, grinning like fools as the blonde giggled and ruffled his hair. Chuck rolled his eyes. Wasn't he just saying how much he liked Blair? Shaking his head, he walked further down the hallway and as he passed the guest bedroom, he heard a giggle.

It was Blair. Her giggle was prominent, high pitched with her young age, delighted sounding with her elated mood. It reminded Chuck of bells. He immediately entered the room and looked around. "Eric?" He decided to please her, making her think that she was the queen of hide and go seek. The giggling intensified, and in the reflection of the mirror hanging on the wall in the corner, Chuck spotted the mop of brown curls peaking out from underneath the bed. He took a second to watch them as they swished back and forth, shining in the light given by the window and kinking at every turn. "Nate?" He guessed again and took a step towards her. His shoe squeaked on the hardwood floor, causing another uproar of giggles to overtake Blair. He watched again as she curled her small body into itself and covered her face with her hands in an attempt to stifle her titters. The boy had to suppress a smile of his own. He allowed himself to smirk as he continued to advance. His hand was so close to pulling off the covers and revealing her when…

"Chuck! Have you found Blair yet?"

Nate's voice was approaching as he ran down the hall, bare feet slapping against the wood and breath coming out in short pants. The smaller boy frowned and quietly walked over to the door, closing it and twisting the lock before pressing his back against the wood. Chuck heard his best friend pass the door and jiggle the knob before sighing. "They're not down here, Serena!" Nate called back to Serena, who giggled and the sound of her tiny heels spinning away made Chuck roll his eyes again. The girl was giving him a headache already.

Lost in his reverie, Chuck didn't notice the small girl that was now looking at him curiously, brown chocolate eyes wide and head cocked to the side, curls falling down one shoulder and brushing against the wood as she peaked her head out from under the bed.

"Why'd you do that?" Blair asked curiously. Chuck's face immediately slipped into a mask of indifference and he shrugged his small shoulders, sliding down the door and resting his elbows on his knees. "We started over." He lied. There was a flash of light in Blair's eyes and she grinned, showing off her teeth. "Does that mean I won?" Her voice held a satisfied edge. Chuck nodded. Why did he lie? "Yeah. Congrats. We started over. Now they won't find either of us." The 6 (now 7) year old found this reasoning to be acceptable and slipped out from her hiding spot, crawling across the floor to join the boy against the door. She looked adorable as usual, white tights and red Mary Jane's matching the black skirt, red blouse, and headband that pulled the curls back from her face.

"Happy birthday." He said again and she smiled at him, well, more like beamed, all dimples and straight, white teeth. She was missing one in the middle and Chuck was forced to listen to her boast about losing her first tooth for about an hour and a half when she first lost it.

"I'm seven today, Bass."

Her face glowed with pride, eyes bright and mouth curved upward. She had taken to calling him by his last name, much to Chuck's displeasure. He returned the gesture by calling her Waldorf (and, because of his missing tooth on the side of his mouth, sounded more like Wawldwarf), which always made the curls bounce angrily as her tiny nose scrunched with her disdain. Perhaps that was half the reason why he still called her it despite her protests. He just nodded, waiting for her to continue the thought.

"That means I'm older than you."

The two, even at such a young age, began to develop a competitive streak.

"I'm taller." was his witty response.

"By an inch."

"Two."

"I'm more intelligent-ed than your useless brain."

"That doesn't make sense, Waldorf."

There was a huff as Blair blew air outward angrily, a curl falling in front of her face that Chuck's hand itched to tuck away.

"Don't call me Waldorf, Bass."

"Waldorf."

"Baaaaaass."She was whining.

"Waldorf."

"Bass!"

Chuck wasn't sure what possessed him to do so, but he lurched forward, curling the brown lock around his finger and pulling once, hard.

The shock on Blair's face mirrored his own and he instantly regretted it when tears blurred her brown eyes.

"Mommy!"

AN: Review, review, review! How will I get any better without anyone telling me all the shit I do wrong? For now, this story will be innocent and light and just so darling, but as it progresses, it'll tread on more serious ground. The rating will probably change and stuff. Thanks for reading! xx