Title: Time Will Tell

Author: RightSide

Disclaimer and Summary: See Chapter 1

A/N: So, this chapter might seem a touch confusing, but bear with me please. Sorry if there are some inconsistencies with Dean's age compared with Sam's if you are a Supernatural fan. And if Chuck seems a little off, I apologize. But I love his character, so this is what he's doing in my fanfic. If it bugs you, feel free to rant.

Chapter 6-

"But come on, the entire series was amazing. I mean 'This is my boom stick!' is classic." Dean argued, unable to believe what he was hearing from this guy. Some people just had no taste.

"The writing was pretty bad ass, I'll admit, but couldn't they have tried a little harder? In Evil Dead the characters are a bunch of college students, and then in Evil Dead 2 they changed the whole plot around. It isn't even a sequel. It's just a redo of the first one."

"Dude, it's awesome, so who cares? Are you telling me you would have rather had it be another Night of the Living Dead? The first couple are great, but when they stretch it out into a fourth and fifth and sixth it just gets ridiculous. Army of Darkness was just as good as Evil Dead, maybe even better."

"Yeah, but why couldn't they have just called it Evil Dead 3? They didn't give Evil Dead 2 a different name." Dan countered.

"Oh, come on! The guy fell into a wormhole and was transported into the dark ages. I think the movie deserves it's own title."

Grabbing another Coke from the fridge, Dean asked his new friend if he wanted any. Weighing the can in his hand, Dan replied that he still had some left. Glancing at the stairs on his way back to the living room, Dean shook his head. The girls had been up there for almost two hours. Serena and Dan had shown up and after a battle of wills the blond managed to drag Blair upstairs to have a private talk. It didn't take a brain surgeon to figure out what the little chat was going to be about. Serena had been glaring at Dean from the moment she walked in the door.

"So, I have to ask, you seem like a cool guy," Dean began as he sat on the couch opposite of Dan, "And Serena's very… pretty, but I dunno. Don't you think she seems kinda… you know… high maintenance?" Dean had no idea how such a down to Earth guy like Dan could be with such a prissy girl like Serena. She was hot, no question. But when you looked at her, really looked, there wasn't much more. That plus the details Blair gave about her extracurricular activities involving the ex boyfriend made his opinion lean more than a little towards the bad side. She had hurt Blair several times. First by taking away the guy she loved and then abandoning her. Even with the psycho chick, Georgia, running around there was no excuse. Someone being that easily reduced to crazy benders had problems.

"No one gets me and Serena. But I knew, the first time I laid eyes on her I knew. I'm not saying she doesn't have her faults. Her choice in friends for one. Not to make you mad or anything, but Blair drives me insane. She's so… well, I won't even say it. Then there's Chuck and the rest of them. I don't get how she can even pretend that they're decent people." Dean knew he should be upset, but he remembered all too well the thoughts he had of Blair the first time she decided to become the worst version of herself in front of him.

And as for the rest of the group? They were all scheming trust fund babies with nothing better to do than destroy each other for sport. Dan was right. Not a decent human being among them. Besides Blair. Maybe Serena, too. If Dan liked her and Blair still tolerated her, then there had to be some good quality buried down deep.

"You've got that right. I don't know how you put up with it."

"I've been asking myself that, too. But Serena likes it, it's how she grew up. Blair, though?" he gave Dean a wide eyed look and whistled, "That's a different story."

"She can be hard to deal with, I'm not gonna lie. We fight. A lot. But it's not her. It's this place, these people," he rested his elbows on his knees, "And I'm leaving in a few days, a week tops."

"You saved her life, Dean. It's up to her to take care of the rest."

"I know. I just wish…" he trailed off as he noticed that the dynamic duo had finally come out from the room. Watching as they still argued in hushed tones at the top of the staircase, Dean and Dan stood and exchanged looks.

"It's nothing personal," Dan said apologetically as he gave Dean a supportive pat on the shoulder, "They don't like that you're changing things. It means that they don't have as much control as they thought."

"Changing what?"

"What do you mean what?" Dan laughed only to receive two sharp glares from above, "When I walked in here I was expecting the Ice Queen in all her glory prepared to hand out a snide comment. Low and behold she's in the middle of a tickle fight wearing no make-up, hair not done, in a pair of loose jeans and a guy's heavy metal shirt. You've taken the Blair Waldorf and made her… normal. Serena's just afraid you're gonna hurt her. And to the rest of the Upper East Side? You're, well, threatening. I like you. And as a friend I have to warn you that these people may look like a bunch of pushovers, but they've got ways. They'll take away everything if you're not careful."

"Then it's a good thing that I don't have anything." Dean joked.

"You have her," Dan glanced up at Blair as she descended the staircase, "That's more than enough." Serena rushed towards them, face tear struck. Taking her arm in his to console her, Dan turned to give Dean a sad smile before leaving.

"I cannot believe her!" Serena screeched, throwing her purse down on Dan's bed. Growling, she plopped down and ran a hand through her hair. Grabbing her phone and harshly shoving her fingers into the buttons, she began to text rapidly. With every response she seemed to be becoming more upset, throat rumbling and nails digging into the straps of her coach bag.

Dan observed the entire scene with an eager curiosity. He had never fully understood the plotting process, or the reasoning behind it. When he had turned to Blair for help with the Georgiana crisis, he had been too desperate to care what he was resorting to. Is that what Serena was feeling now? Or had she been doing this type of thing for so long that it no longer took such a strong emotion to make her plan the destruction of another human being?

"You should have heard her, Dan," she began, closing her phone with an air of finality, "I mean, she wasn't even being mean. She just didn't care. I tried to tell her, you know. I tried to explain how much she'd changed, and how she was starting to lose her real friends. You know what she said to that?" Dan waited for her to continue, thinking it was a hypothetical, but soon realized she was awaiting his answer.

"I don't know. What did she say?"

"She said, 'What real friends?' Can you believe that? And she started bringing up our entire history. I mean, things I thought we were past by now. But obviously not. So, I thought to myself, maybe if I'm just really direct she'll finally get it. So I told her. I told her that he was going to leave her and that when he did she'd be lucky if she had anyone left. And do you know what she did then?" she didn't bother waiting for his response, "She said she didn't plan on being left." Serena spat the words as if they were acid on her tongue.

"It'll be fine, I promise," Dan whispered as he tried to comfort her, "Dean said he was leaving in a few days. He won't be around for much longer."

"You talked to him?" she pulled back, seeming stunned. Blinking back tears, she began to analyze him.

"You were up there for a long time. What was I supposed to do?"

"Well," her eyes brightened; Dan could see her mind turning, "What did you talk about?"

"A lot of things. Why?" his voice dropped low, face twisting into a mask of disgust. Was she honestly going to do this?

"Chuck and Nate can't come up with anything on him. As far as we know he's a regular John Doe from Kansas with a smart brother, Marine Corp dad, and mom who died when he was little. Maybe if we had someone who he could trust. Someone he could relate to…" she trailed off, the look of hope on her face disguising her true intentions.

Dan smiled sadly he bent his head down low to give her a full kiss on the lips. Slightly stunned, Serena responded gradually, wrapping a hand around his neck to pull him closer. Balancing his weight on his elbows, he lowered himself over her, lips following the trail his fingers made as they deftly removed any annoying pieces of fabric that got in the way. Groaning as she shifted beneath him to make their position even more compromising, Dan quickly released her and took a step back.

"I like him. I'll be friends with the guy while he's here, but I won't help you mess with his head. As far as I can see, he's done more good than anything." Watching as Serena readjusted herself, he awaited her reply.

"Fine. But if he's such a great guy, you won't mind telling me what the two of you talk about."

Dan grunted.

"Fine," he crawled back over her, burying his head in the crook of her neck, "Could you be more of a pain?"

Chuck stood nervously clutching the end of his trademark scarf. Scanning the entrance again for any sign of his Blair, he clicked his tongue and checked his phone. No new messages. Of course not. They had been searching for days only to end up with… nothing. This Dean was a ghost. A modern day magician with no paper trail, no job. He existed for seventeen years in reclusive holes of random home schooling and not even as much as one trip to the doctor for a cold after age six. It was unnatural, and it made Chuck's life so much more difficult than it needed to be. So he came, without permission from Serena or Nate he stood on the Queen's doorstep lurking, calculating. He could just imagine the headlines on gossip girl.

Seen: Chuck Bass himself sneaking around Queen B's. What's the matter, Chuck? Afraid you might lose what you already threw away?

A flash of perfect brown tresses caught his eye, and Chuck snapped out of his reverie. This wasn't the Blair Nate allowed to cling to him, or the one who would stand in front of the mirror holding her stomach as she trembled before her warped vision of her own starved frame. This was a different creature altogether. She must have gained a few pounds, her arms no longer angular sticks of jutting bones. Her eyes were soft, skin clean, clothing plain, yet passable in terms of society's standards. He nearly gagged at his next train of thought.

She was glowing.

Hesitating with the help of the conscious he was so quickly beginning to tire of, Chuck stood stock still for a few beats before heading towards the double doors. Every instinct he had told him to turn and run. Hell with the girl, let her learn from experience…

The elevator doors opened, and he calmly stepped inside, nodding coolly to the doorman. Attempting to steady his breathing, he began rocking on his heels. Back and forth, back and forth. Blair needs this. He'll leave her. And when he goes she'll be more broken than before.

The apartment was empty. Checking and double checking, he eventually gave up and poured himself a glass of scotch. Blair was off to Serena's to make peace for the havoc that had occurred the day before. Using Dan as a spy? He chuckled at the mere thought of it.

He had two or three hours before the goddess came home, leaving Chuck with the option of stretching out across the leather sofa to wait. Always waiting. Only this time it wasn't for Blair. It was for Dean. Because Chuck had found the weak spot, buried down deep. And he was willing to exploit it, whatever the cost.

Blair glanced around the apartment and sighed. If Dean was back music would be blasting and she would have already caught sight of the abnormally adorable grin she had grown to know and love. Fingering the material of the jacket Dean must have haphazardly tossed on the couch earlier, Blair frowned. Hadn't he been wearing it that morning? And if he was already back, where was he?

Slowly climbing the stairs and unconsciously holding her breath, she crept her way to the door to her room. Instantly she recognized the sound of voices, but whose?

"You couldn't. Not even a rich boy like you could afford-"

Dean.

"You would be surprised what a 'rich boy' like me can do." Chuck said. She could imagine him sitting there, lips turned into something that resembled both a grin and a snarl as he watched the wheels spin in Dean's head, knowing that he was already one step closer to accomplishing whatever demented goal he set his sights on. Dean wasn't prepared to handle this. Not yet. He had no practice dealing with the maniacal manipulations of the Upper East Side.

Her heart plummeted. Would he allow himself to be bought? Her knight? She knew she was ridiculously enamored by the sight of him. She knew her affections were horribly childish, but Blair couldn't bring herself to care. In the course of a couple of weeks all of her faith in humanity had come to rest in his hands.

"You expect me to believe that as soon as I'm gone you'll keep your word?" Dean's tone was menacingly contemplative.

"Yes. He's already in. All that stands in the way is paperwork. I have the connections. If Sammy gets a letter saying tough shit, you could always come back and do whatever it is you're about to threaten to do to me."

"You don't understand. I'd never-"

"You'll agree because it's Sam. Your little brother. And something tells me that you'd do just about anything to keep him safe. To let him have a normal life. With my help, you can give him that. Or maybe I overestimated you. Maybe you really are that selfish…"

Damn him, Blair thought. Damn everyone who ever told her life was grand and easy and that good people end up happy and bad people are tossed aside. Hadn't she given enough to earn a chance, just one chance, to be loved? To be happy? Hell, she'd settle for decent. Anything that meant she wouldn't have to be guarded all of the time with only Audrey Hepburn movies to keep her company.

She heard a whisper, a disgusted, self pitying kind of whisper come from Dean. But Blair couldn't listen. Going back to the lobby, she paced and cursed and when she finally saw the elevator open again to reveal a satisfied Chuck strutting out she was in front of him before she realized what she was doing. The slap echoed and every head turned to witness the episode they were so sure was about to occur. Seconds lapsed upon minutes as she stared at him, tears streaming down her face, breath coming out in weak sobs.

He spoke, at first in a stutter and then softly, slowly.

"I had to."

Her head dropped in defeat, in agony, and she walked away.

Chuck watched as her form passed through the doors and beyond the line of cars piled up in the street. Purposefully, as if she knew where she was headed. He knew better than to follow. Somewhere between the look of complete loss on Blair's face and the point when her dejected body vanished in the mass of humanity that was New York, Chuck came to the conclusion that he had made the right decision.

As he glanced back at the building through the tinted glass of the limousine, his nonchalant mask gave way to an exhausted, crestfallen smile.

"So, do we have a deal?"

Dean nodded, "Yeah, we have a deal."

"Then we're done here. Tell your brother congratulations on the full ride to Stanford." Chuck stood to leave.

"You gonna tell her goodbye?"

"No," he paused, thinking it over, "If I did, she'd know."

"I'll take good care of her."

"I know you will," sighing, he managed a grin, "You make her happy. And if any of us deserve happiness, it's her."

A/N: Next chapter we will see the response from the rest of the Upper East Side. Will Blair go with Dean? Will she realize how much Chuck loves her? Will she die in some horrible Supernatural accident that makes all of you hate me?

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