Chapter 1)

Chuck’s head hurt as he turned on the small light near his bed. He was alone, not a common occurrence. There was always a woman or three willing to share the night with him. Blair’s little birthday bash had been, painfully memorable. Chuck sighed; he had resigned himself to being Blair’s friend and nothing more years ago. It wasn’t even that bad, he wasn’t exactly pining, he liked women, in the plural sense. But, Blair, well she was something. It had astounded him when he realized that Nate wasn’t into her anymore, but still he had tread carefully. Chuck had never expressed interest in Blair, he wasn’t stupid, he was never going to let her know how he felt about her. Never, he though vehemently. However, when she had come on to him, he wasn’t about to say no. He could hear himself asking her if she was sure, like some pathetic schoolboy. He was not that type, he took, with no fear no trepidation, he didn’t ask….. But still it had happened, she wanted him, and he took her.

And then the next day, he was nervous, was she going to expect something? Could Chuck be depended on? Probably not. This upset him. But, no, she ran back to Nate the moment he curled his finger. He could hear her voice in his head, ‘From this moment on the events of last night will never be mentioned again.’ Who the hell did she think she was? He wanted to scream at her that Nate didn’t love her, that he was in it to help his dad with his failing business. But, Nate was his best friend, and well Blair was Blair.

Chuck was good, or tried to be, until he slipped to Nate that he knew that they had ‘broken up’. He covered. Seeing the engagement ring had felt like a punch in the gut. It really hurt. And then they did break up, and Blair was convinced it was Chuck’s fault. But, hell, he couldn’t actually remember telling Nate anything about the night in the Limo. He was drunk before the party even started, and all he could remember about it was Blair’s accusations. It was a blur. Chuck decided he needed to get out of New York.

Chuck made a few calls and arranged to spend the rest of the weekend in Aspen. He conveniently left his cell phone at home. No need to face the music, before Monday. The weekend was fantastic, his father had a plush resort with plenty of snow bunnies lining up to warm him up at night after his cold days spent on the slopes. Damn, did he love Aspen.

He did call his father, who wanted to set up a meeting to run through a few iterations of the business plan. Chuck smiled to himself after the conversation. He didn’t need Blair or Nate.

School on Monday started strangely. “Hey,” He said, as he sat down next to Nate. “What’s up?” Chuck decided to chance a fight, he couldn’t stand seeing Nate eating lunch alone, looking so miserable.“What do you think is up? My father is in jail, my mother is pretending that nothing is wrong, and Blair and I are over.” Nate played with the food on his plate.

“Look, I’m really sorry about that. I didn’t mean for anything to happen.”

“What the hell are you talking about?”

Chuck raised an eyebrow. Nate didn’t know. How was this possible? “I just mean I’m sorry about what happened.”

“Yeah well, I don’t know what I’m going to do. We’re going to lose everything. The house, the money, the cars…our reputation. I called our families lawyer and he said my trust will be fine, but that I should change all of the account numbers and passwords so that my parents can’t touch it. Can you believe that?”

“Nope. Look, I’ll talk to my dad, maybe he can help out your family somehow.”

“Don’t worry about it, we have a lawyer.”

“I’m sorry I wasn’t in town this weekend. I should have been around.”

“It doesn’t matter.”

“Are you sure? You know I’m here for you man.”

“Yeah, of course. You, know, I’m glad that things didn’t work out with Blair. I feel like I’ve been lying to her for a long time. At first, I wanted to fix things; I really thought it would be best for the family, but then…. It just wasn’t fair to her or me. She thinks she loves me, but you know what, I don’t even think she really does.”

“Did you break it off with her?” Chuck asked carefully.

“Yeah, I just told her I couldn’t do it anymore.”

“Really?”

The lunch bell rang, and class started up again. Chuck entered his English class and sat in the back, and put his feet up on the back of the chair in front of him. He grinned.

After he met with his father he went to the hotel’s bar, and ordered a drink. The conversation had gone surprisingly well.

“Hi,” Blair sat down next to him. “So you didn’t tell Nate…”

“Nope.” He pursed his lips.

“I thought you did. I’m sorry.”

“Whatever,” Chuck stirred his drink carefully.

“Yeah, well I just wanted to let you know.”

“You were pretty quick to think it was my fault.”

“You aren’t exactly Mr. trustworthy.”

“That I’m not.”

“Well, my informants also tell me that your one time failed conquest, little Jenny Humphrey, has her eyes on Nate.”

“Really?” Chuck smirked.

“I think, that she needs to learn that no little freshman moves in on my ex-boyfriend.”

“And just how do you propose to exact revenge? And why are you telling me?”

“Well, I think I might need your help.”

Chuck smiled. “Why should I help?”

“She was the one who stole your clothes the night of the masked ball, and left you high and dry on the roof. She switched masks with Serena.”

“No kidding. Well, then Blair, what’s your plan?” Chuck smiled. He didn’t really care that Jenny had taken his clothes. But, damn did he want an excuse to cavort with Blair.