December 20, 1997

The Waldorf Penthouse

New York City

Six year old Chuck Bass ducked out of what had been deemed the "kids' room" of the Christmas party in the home of Harold and Eleanor Waldorf. The kids inside were stupid and playing games for babies, in his opinion. One little boy, he was pretty sure, had picked his nose and then proceeded to eat it. He shuddered at the disgusting memory and went in search of something more entertaining with people that didn't repulse him. He hadn't wanted to come to this party in the first place. He'd have rather stayed at home watching a movie or reading, but his father and future step-mother had insisted that it would do him good to meet some of his new classmates before the next school term started. His soon-to-be step-sister, Serena, was around here somewhere. She must've been smart enough to know that the "kids' room" would be lame and wisely avoided it at all costs.

As far as future step-sisters went, he guessed she was alright. It wasn't as if he'd had a sibling before to compare, but she didn't annoy him too much and they got along well enough—even though they didn't really like the same things at all and she was always flittering about and constantly moving. He didn't think he'd seen her stand still for more than ten seconds at a time. Chuck preferred to sit back and observe others, to take in everything around him. He found that infinitely more interesting than the go-go-go style Serena possessed.

Voices floated through the air from a door at the end of the hallway. The voices sounded vaguely familiar and he carefully peered in through the door that had been left ajar. He saw that the room was empty save for a little girl that appeared to be about his age lying on her bed watching a movie. Chuck quietly pushed open the door and entered dimly lit pink room. The girl had long hair, the color much like his own, a dark brown that he'd heard described as chestnut. Hers was curled and adorned with a red headband that matched the red velvet of her dress. "Is that Breakfast at Tiffany's?" he asked, startling the girl.

Blair shrieked and pushed herself to her knees, grabbing a pillow to either throw at, or shield her from, the intruder. "You scared me!" she admonished. "What are you doing in here?" Her little heart raced as she stared at the boy before her with the curious dark eyes and amused expression twisting on his lips.

"Sorry I scared you," Chuck said, walking further into the room, despite not having been invited, to stand before the girl with the dark curls and porcelain skin. "I heard the movie and I thought I'd come watch it."

"Who are you?" she asked snootily.

"Who are you?" he shot back, crossing his arms over his chest, a move he'd seen his father do countless times.

"I asked you first," she clipped, throwing her pillow down on the bed and placed her fisted hands on her hips. "This is my house, so you'd better tell me before I have you thrown out."

"You must be Blair Waldorf then," Chuck replied, smiling at her annoyed expression.

"I am and you still haven't answered my question."

"I'm Chuck Bass."

"So you're Chuck Bass," she said, a sneaky smile on her lips. "Serena told me about you. Shouldn't you be down in the room with the rest of the kids?" she asked, arching a brow.

Chuck smirked and laughed lightly. "Have you met the kids down there? Half of them probably haven't learned to stop eating paste and once the booger eating began, I had to get outta there."

Blair giggled and covered her mouth. She didn't like any of the children in that room either and decided that she and Chuck were the same in that regard. "They are losers," she agreed. "That's why I hide out in here when my mother insists on inviting them to our home."

"Why don't you hang out with Serena then?" he asked.

She shrugged. "I do most of the time, but she can't sit still long enough to watch a movie. She's probably off chasing after Nate Archibald anyway."

"Jealous?" he inquired with a smirk.

Blair rolled her eyes and scoffed at his suggestion. "No. Serena can have Nate Archibald. He may be the cutest boy in our class, but he's only one step above the paste-eaters in my opinion."

It was Chuck's turn to laugh, which he did, having been pleasantly surprised by her candor. "Can we watch the movie now?" He sat on the edge of her bed and saw her hands fist at her hips again.

"I didn't ask you to sit down, Chuck Bass."

"What's the big deal, Blair Waldorf?"

"How do you even know this movie?" she wondered.

Chuck shrugged, "My nanny made me watch this with her one time. It's okay."

Blair's little face was incredulous. "It's better than okay. This is the best movie ever made. I want to be just like Audrey Hepburn when I grow up."

He found her statement rather silly, but he knew better than to say so. Instead, he fought the smile and merely nodded in agreement. "Can I watch the best movie ever made then or will you send me back to Loserville?"

She cocked her head to the side and studied him intensely for a moment before making her decision. "I guess it would be alright for you to stay. Besides, you're going to be Serena's step-brother and we'll be in the same class." Blair scooted over to the far side of her bed and lay back down on her stomach, propping her chin on her fists. Chuck followed suit, miming her actions and laid down beside her.

Blair felt him looking at her and she turned her head. When he grinned at her, she rolled her eyes. "Nice bowtie."

Chuck smirked and replied "Nice headband," before turning his attention to the playing movie.