Author's Note: This is my first real fanfiction with chapters. I should warn you that even though this is technically a Blair and Chuck story, it also has a whole bunch of Serena and other characters in as well. After you read this chapter, you'll see why this is necessary. Why did I write this story instead of writing something about the current plotline? That's because I think the current plotline sucks. Yeah, Blair and Dan don't really work for me. Neither do Blair and Jack, which is why I'm writing this. I hate how the writers handled that plotline. I don't even like watching the Blair/Chuck reunion scene in the season 2 finale anymore because of what happened right before. So, here's my version of what should have happened.

P.S. This chapter is actually more of a prologue, but if I called it that, it would mess up all of my other chapter numbers. So I'm just going to call it Chapter 1.

Disclaimer: If I owned Gossip Girl, do you think I would ACTUALLY allow Blair and Dan to kiss? Ever? My, you misjudge me so.

Chapter 1

Sighing, Serena let herself into her house. This was pretty much the worst winter holiday ever. First her step-dad died right before vacation, then her step-brother ran away, then she further ruined her vacation by breaking up with Aaron, then she went to tell Dan she still loved him, only to find out they shared a half-sibling. She guessed they wouldn't be rekindling their romance anytime soon. Now she was back home for New Year's Eve, hoping she could just lock herself in her room for the rest of the break.

She stepped into the living room. "Mom?" she called. Before she locked herself in her room, she wanted to know more about her half-brother or half-sister. She stopped when she found Lily talking to a man she'd never seen before. He was good-looking enough (for his age) and he seemed easy-going, but there was something Serena didn't like about him.

"Serena, what a pleasant surprise!" Lily exclaimed, walking over to embrace her daughter. "What are you doing back so soon? Didn't you have a good time with Aaron?"

"We broke up. Actually, mom, there's something I need to talk to you about." Serena looked upset, but she couldn't talk to Lily with that strange man there.

Lily looked over at the man. "Can it wait? I'm in the middle of something right now. Serena, this is Jack Bass, Bart's brother and Chuck's uncle. Jack, this is Serena, my daughter." Jack grinned and held out his hand.

As they shook hands, Jack's eyes went down to her cleavage. "It's a pleasure to meet you." Jack said, with a sleazy grin on his face. Serena shuddered. Jack sure was a lot like Chuck. At least Chuck was still a teenager. What was Jack's excuse?

"It's funny; I didn't know Chuck had an uncle. He never mentioned it." She told him, giving him a look of complete disgust.

"Yeah, well, that's my nephew for you. Always hiding things. Unlike you." His eyes slipped down to Serena's chest again and she took a step back.

Lily was getting creeped out by the way Jack was looking at her daughter. She quickly stepped between them. "Jack is here for Bart's will. He's also trying to find Chuck. Apparently." She added the last part with a glance in Jack's direction. Serena smiled a little.

"It was nice to meet you, Jack. I'll talk to you later, mom. Where's Eric?" Serena backed out of the room as quickly as she could.

Lily sighed. "He's in his room." She watched Serena leave and then turned back to Jack. With that, Serena headed to Eric's room.

"Eric? It's me. Can I come in?" Serena knocked softly on Eric's door. She wondered why Eric wasn't with Lily and Jack, but she already knew the answer to that.

"Serena? Come in!" Even through the door, Serena could hear Eric's surprise. She smiled and entered his room. Eric was lying in his bed, reading a book and listening to his Ipod. He took his earphones out when his sister came in his room and sat next to him on his bed.

She ruffled her little brother's hair and hugged him. "Hey. I'm back early. Why aren't you with good old Uncle Jack?" she teased him. Eric hugged her back, but his face darkened when Serena mentioned Jack.

"That guy's creepy. I don't like the way he looks at mom."

Serena nodded. "I don't like the way he looks at me."

Eric smiled a little. "So why are you back so early? Did you and Aaron have a fight or something?"

"No, we didn't have a fight, but I broke up with him. I love Dan. I went over to his loft to tell him that before I came here, but he told me something bad." Serena looked at Eric closely. "Guess what, Eric? You, me, Dan, and Jenny all share a sibling. We're not related to each other, though. Thank God."

The look on Eric's face made her giggle. Eric laughed with her. "A-are you serious?" Eric stammered between laughs. "This family is so screwed up! We might be step-siblings someday!" Suddenly Eric stopped laughing. "Hey, you and Dan aren't getting back together, are you?"

Serena gave her younger brother a sad smile. "I don't know if we can get past this. It's just too much to handle right now. We both need time to think." She sighed. "I still want to go out with him, but I just don't know if it's possible anymore." Just then, they heard a knock on Eric's door and Jack popped in. The van der Woodsens weren't very pleased at his intrusion.

"I'm heading out now. I've got a meeting with somebody important. I'll see you tomorrow. Maybe we can get to know each other better." Jack laughed and closed the door again. Serena and Eric shared a disgusted look.

"Jack has been here before?" Serena asked, surprised.

Eric made a face. "Yeah, he's been here every day for a week. Mom keeps trying to get him to leave, but she's too worried about finding Chuck to run Jack out of town."

Serena wondered why her mom couldn't just try to find Chuck herself. She stood up and stretched. "It's great to see you again, but I think I'm going out for a bit. See you tomorrow?"

Eric waved and went back to his book. "See you tomorrow. Oh, by the way, Jack's joining us for New Year's brunch. You'd better be there." His sister left his room and he put his earphones back in his ears, smiling to himself.

On the other side of the door, Serena rubbed her head tiredly. Damn, she needed a drink. Or a few drinks. Even though she didn't drink as much as she used to, this was one of those times where she needed to let loose. The Palace Bar was a perfect place to do exactly that.

At the Palace Bar, Serena went straight for one of the barstools in front of the counter. Before she could reach the stools, she did a double take. Was that Blair? She smiled giddily. She was planning on visiting Blair in the morning, but it was even better to see her now. Just then, Serena stopped in her tracks. Who was that beside her? It was a man who looked a lot like Jack, but that was impossible. Blair didn't know Jack, and if she did, she wouldn't associate with him. The man turned his head, giving Serena a better look. No. No no no no no no NO. It was Jack. Blair was the person Jack was meeting?

What the fuck? What the FUCK?

Serena's mind raced to find a plausible explanation. When she found one, she could breathe again. Of course! Blair wanted to find Chuck and she was coming to Jack for information! She calmed down, but something still didn't feel right. The explanation made sense, so why was Serena still feeling uneasy? Something was wrong.

The confused blonde watched as Blair and Jack stood up to leave. Serena paused, torn on what to do. One part of her told her to leave her best friend alone and to forget about the whole thing, but another part of her told her to follow the two of them. Not surprisingly, she waited until they were far enough away, and then began to follow them. They were heading upstairs towards the suites. Alarm bells rang in Serena's head, but she forced herself not to jump to conclusions. There's no way Blair would do that. She loves Chuck. Doesn't she? A million thoughts rose in Serena's mind.

Hardly able to breathe, Serena quietly followed Blair and Jack up the stairs. Already a swirling feeling rose in her stomach, but she tried to ignore it. They walked down the hall, with Serena fifteen steps behind them. Don't turn around, don't turn around…she silently begged. Finally, they stopped at the door of a suite. Serena panicked. She had to stay to see what was going on, but they would see her if she stayed there. She spotted a large plant and ducked behind it. As long as they didn't suspect anything, she should be safe.

They talked for a while in front of the door. See, it was silly to jump to conclusions. They probably just came up here to talk about Chuck in a quieter environment. How should I leave without them seeing me? Serena thought, her brain switching ideas to work on getting out of there without being spotted.

Something inside of her made Serena look back at Blair and Jack. Immediately she wished she hadn't. In front of the door, Blair and Jack kissed. The kiss quickly turned into a make-out session. Serena froze. With one hand, Jack opened the door to what was presumably his suite and he and Blair stumbled inside. The door closed shut behind them. Serena's winter vacation suddenly got a lot worse.

Serena felt sick.

This was like the time when Serena caught Blair and Chuck making out at Blair's birthday party, except this was worse. So much worse. Unless she was wrong, Chuck wasn't Nate's creepy old uncle. Even if he was, the situation still wouldn't be the same. What the fuck was Blair thinking?

Shakily, the girl stood up and ran downstairs. She was so angry and she didn't even know why. Maybe she did know, deep inside, but at that moment it didn't matter why she was angry. The point was that she was pretty fucking pissed. Actually, she was furious. She was also shocked and confused, but all she could feel was immense anger. She stopped running to briefly lean against a wall and sighed dejectedly.

Fuck, now she really needed that drink.