A/N: Okay this a fanfiction that's basically a modern day Chuck and Blair AU based on the story of Bonnie and Clyde. There are a few differences from the show, like Serena is not close with Nate and barely knows Chuck, and Blair is new to the Upper East Side. There will not be a Derena endgame at all nor will they ever be in a relationship in this story. Chair is the primary ship of this story so please don't expect any Dair, Nair, Blouis or any other ship including either of the pair that isn't Chair.

Disclaimer: I do know own any of the characters.

Chuck stood on the rooftop of the empire with Nate, they had been planning this party for while, it was an annual event for the elites of the Upper East Side, and this year Chuck and Nate were hosting. Chuck watched Nate reach towards his pocket and pull out a pack of cigarettes. Chuck was trying to quit smoking but honestly, he didn't want to refuse, he craved the taste of nicotine, he could already taste it on his lips. Chuck pulled a cigarette from the pack without a second thought, temptation was a terrible thing. Chuck let Nate light it for him, and he took a long drag, savouring the feeling it left him before looking back at his best friend. The conversation took a turn that Chuck hadn't expected, Nate had brought up Bart Bass. He wasn't surprised in the least. Bart Bass was becoming something of a legend in the world of business and it was only natural people wanted to talk about him. But Chuck wasn't people and Bart wasn't someone he wanted to talk about.

People began to slowly pile onto the rooftop which was now being filled with some of Manhattan's finest women wearing some of the finest yet yet at the same time the skimpiest clothes that Chuck had ever seen, and to say that he was enjoying it would be an understatement. He watched a few of his friends walk into the party, but in all honesty he'd rather just stand there for a while with Nate. The rooftop was now crowded with people, and the music had become louder, but hardly loud enough to drown out the sound of the busy New York nightlife.

Still, Chuck slowly let Nate's voice become monotonous as he focused on the sirens he could hear in the background, letting himself slip into a daydream.
"Chuck, did you hear me? That's her there." Nate stated he before continued.
Chuck snapped his attention back to Nate at the sound of the question only to find his eyes drawn to the door where she stood. Without diverting his gaze he lifted the cigarette to his mouth once more before flicking it to the ground and putting it out.
"Who is she?" He asked Nate, his face clean of any emotion.
"Her?" Nate said rhetorically, "That's Serena Van der Woodsen. I'm surprised you don't know who she is Chuck, of all the girls in the city you pick her to be the one you don't know."
Chuck almost rolled his eyes. "Not the blonde Nathaniel, her."
As if it was rehearsed Nate lifted the cigarette to his lips dramatically, and watched her, "Ah, that would be Blair Waldorf."
"Details, Nathaniel." Chuck snapped back sounding like a drill Sargent turned Manhattan socialite.
"There's not much to say really aside from the fact she's my best friend of my date for tonight, her mother owns some fashion company and she moved here recently."
Chuck ignored the fact that he came with a date before he sighed and replied, "You're not much of a help you know, I'll just have to go find out about her myself."

Chuck took one last look at Nate before making his way through the crowd and finding himself two champagne flutes and walking over to the to the door where the two girls stood talking idly.
"Serena," he greeted with a brief nod of the head, as he turned away from the blonde and turned his attention to Blair he could practically see Serena's eyes roll. As Chuck noticed Serena leave he lifted Blairs hand and gently kissed it, "Miss Waldorf," He said quietly yet full of confidence, he gently dropped her hand, "It's a pleasure to meet you."

Chuck watched the brunette blush slightly, a colour that made him understand why cheeks could be called rosy burned against the pale white of her unmarked skin. But her next reaction surprised him, he was attracted to her before but as Chuck watched the brunette smile almost wickedly he realised just how much danger he would be in if he stayed with her. Chuck watched Blair's facial features shift into something that showed her superiority, her eyebrows raised questioningly. Chuck Bass was rendered speechless by her confidence as he waited for the words she was clearly about to speak.
"Of course it is, you are after all in the presence of Blair Waldorf..."
Chuck smiled clearly amused by the girl, "I'm Chuck Bass."
Another one of those devilish smirks were awarded to Chuck, "And I suppose that's supposed to mean something to me." Chuck folded his arms and smiled gently, he could get used to this.

Behind them, the party was in full swing, just as he had hoped it would be by this time earlier in the night. Chuck prayed that, that would not be the end of their banter, there was something about that girl and her wicked smile that he thought he could easily get lost in. Chuck looked back to his hands noticing he still carried the two flutes of champagne, and Blair must of noticed too. "Do you have diabetes or do you find joy in carrying two glasses of drink around for yourself?" She asked with her eyebrows raised her face not displaying anything rather than complete and utter seriousness.
Chuck's face showed an expression of incredulity, he couldn't help it, the girl was so blunt and forward that he couldn't help but want to snap back at her. He didn't though, "No I don't have diabetes Waldorf, I thought it'd do my good deed for the day and bring a lovely young girl like yourself a drink." He said finally extending the cup to her.
"Thanks for the offer, but I don't accept drinks from strangers," she paused for a moment, "and especially from a guy who smokes." Chuck stood there for a moment staring at the brunette who had now stepped back from him and he smirked, he didn't need the cigarettes, she was already becoming just as addicting. Chuck watched the girl spin around in the other direction on her heels, he watched her until she got lost in the crowd. He held the glass up to his lips, this wasn't the last he'd see of Blair Waldorf.