A/N: This is the first chapter of my new fic. I've been writing many multi fics, lately. It's Chuck and Blair in their past lives, how they find each other each time because they're soulmates. This was my first one, and it may not be very good, but I have better ones coming up. Each story takes place in a different era. They aren't given names and only referred to by the pronouns "he" and "she" because they would have had different names in their part lives. It's also because they are described by their characteristics and they could have any name. I hope I haven't made it too confusing. This one is supposed to slightly mirror Victor, Victrola. Sorry for any inaccuracies.

Disclaimer: All rights of course go to Gossip Girl, the CW, and the people who created them. I would like to thank Katelyn for helping me with the era of the Roaring 20's to get most of it right. The only other research I did for this piece was watching "Thoroughly Modern Millie" and Chicago (the movie.)


He smirked. It felt good to smirk. It was his signature expression. But he found that he was smiling more and more now. Not just smirking, but… smiling. If anyone told him that he would be smiling—because of a girl, no less—he would have asked what they were on, and could he have two of them.

The place smelled like it always had, like it always would be. 80 years from now when they turned it into a burlesque club or something, it would still have the same scent of booze and cigarettes.

He loved it. This was his world. He owned it. Everyone knew his name and the power he held. Everyone knew his influence and respected him for it… even if they were a little afraid as well.

He straightened his white jacket as he walked in the place. His place. He caught his dark and angular reflection in the mirror above the bar. His smooth appearance was just one of his trademarks.

As soon as the bartender saw him, he was immediately made his scotch. He eased into the seat next to her; the woman who was the source of his smirking. She pretended to not notice him, but he recognized the stiffness in her posture, the tenseness in her shoulders. It could not be seen by the naked eye, but he knew her better than anyone.

He knew the effect he had on her. More importantly, he was painfully aware of the effect she had on him. He took an easy sip of the amber liquid that burned down his throat as the band struck up her favorite jazz tune. He knew her so well.

Chicago, Illinois, 1922

Establishment of the youngest speakeasy owner in history

He wondered how long she could hold out. He assumed it would be awhile. After all, she was his perfect match, and he could hold out for hours. He watched her tap the ash of her expensive French cigarette on the ash tray in front of her.

She had a pull for him that he couldn't explain. He should have realized it sooner, when he first met her. He thought that she was just another broad with nice legs. But even now, he could recognize what he felt that first time. The first time he saw her on stage. The first time she rebuffed him with her wit. From then on, he was a goner.

She would come her more and more often, but she didn't used to. This wasn't the first place they met, but he wanted it to be the place that she would stay. She wasn't flighty by nature, but she was unpredictable. She liked putting on the façade that she was completely put together and pristine. That didn't really coincide with her alter ego. It didn't really agree with her when the whole place saw that beautiful flapper take the stage.

When he walked into that place, he had planned on buying it out. He bought his first place when he was 16—with the help of his father, of course. Now, he was the youngest ever in history to own a bar of any sort. But this place was his favorite. It was his first. Just like her. She was his first, in a way. The first to capture his cold, black heart.

He walked into that joint on the pretense of flaunting his money, letting everyone now who he was, because everyone knew his name. To say he got side tracked would be an understatement.

He wasn't really looking at the stage at first. All those flappers were all the same. He had ordered his standard scotch, as usual. That was when his life changed drastically.

Against the backdrop of the rest of the shiny flappers, she didn't stand out to anyone but him. She was in the throng of many. But he could see her. She stood out for him, unlike any of the others. They were just doing the normal moves that he had seen a hundred times over.

It was like the light was shining on her. Her silvery frays danced around her as she spun. Only reflecting now he could see what it was. It was her eyes. Her onyx eyes that showed him something he never thought he would see. Emotions burned in them. she was beautiful and flirtatious and lively. He had never met any one like her.

He realized this especially when he talked to her for the first time after the show. She raised her eyes to his with a superior air and smug look while she verbally barbed him. No one had ever done that. No one would dare. From then on, he couldn't look away from her. He wouldn't be able to stand it.

"Have you considered my offer?" he leaned in close to her and whispered darkly into her ear, not able to ignore her fragrant scent.

She finally swiveled to face him. Her face betrayed no emotion as she took him in.

"Oh, I've considered it," she finally replied, pushed her bobbed curls away from her face.

"And what's your answer?" he asked.

"I already told you my answer," she reminded him.

"Not that answer," he shook his head, smirking playfully.

"What other answer is there?" she asked, complying with his badinage.

"The right one," he supplied smugly. With that she rolled her eyes. But he did catch the way her mouth twitched at the corners. He knew her well enough to know she was hiding a smile.

"You're a little too egotistical for your own good," she retorted.

"Actually, I'm a lot egotistical," he corrected. "It's better when you just admit the truth to yourself. Like how you want to say yes."

"And why would I do that?" she asked in a hushed whisper.

"Because it's a smart move," he answered, leaning back confidently. He took another sip. She followed suit and took a pull from her silver flask. He smirked. She was so convinced that everyone thought she was perfect. Well, everyone did. He was the only one who saw the real her, no matter how much she didn't want to admit it.

"I'm fine where I am," she said. He couldn't help but notice how she wouldn't reach his eyes.

"Really?" he asked. He couldn't think of a better response. But he knew he was headed in the right direction. He had been pursuing her for a while now and he was wearing her down. It wasn't really something he was accustomed to.

Women usually didn't evade him at all. He had never tried to "woo" a woman before. They just fell into his lap. Figuratively and literally speaking. But when the occasional woman did not respond to his advances, he just moved onto the next one.

That was the problem with her… and him. He just couldn't let her go. He had never felt this way before and it was strange for him, but came naturally in a strange way. Chasing her came naturally to him, like he had done it before.

He could tell that she wasn't used to this sort of attention, either, though he couldn't fathom why. She was the most desirable woman he had ever met. He could tell that she wasn't used to feeling beautiful. He would make her feel beautiful.

She just spared him a look of disdain. She really was perfecting those hateful glares.

"You can honestly tell me you are perfectly content at dancing at some low rent bar for the rest of your life?" he asked softly.

"As opposed to dancing at this low rent bar?" she quipped.

"You wound my pride," he held his hand to his chest in mock pain.

"You can buy that place easily, what do you want from me?" she asked seriously.

"Only what I've already told you," he matched her tone. "I want you to work here." He didn't know why he was so sold on the idea. Maybe it was the fact that he loved this place as much as he loved himself—which was a lot. He wanted to merge the two things that he loved most in the world (besides his own self absorption.) He didn't like using the term "love" for a woman. He wasn't even sure if that was he was feeling—he had never felt it before. But he was certain that if he wasn't already, this was as close as he was going to get.

He wanted her to work in his favorite building because it was an easy way for an excuse that he could see her all the time. He wouldn't have to travel all the way out to that rival establishment to see her. And she was right, he could just buy it. But he wanted her here, with him.

He didn't think he was ready to put it all on the line—to tell her his true feelings. He had never done that either, because he was convinced he didn't really have any. That was, he was convinced of that until he met her and his world came crashing around his ears.

"You can't own people," she snapped. He held back a smirk. She was finally reacting to him. This was a good sign. "Just because you have money, doesn't mean you own everything."

"You have money too," he reminded her. she rolled her eyes. "And you could have more."

"What's that supposed to mean?" she asked.

"I'm just reminding you how beneficial working here would be," he said simply.

"Like what?" she pressed. He hid a smirk. He knew she didn't like being kept in the dark. She was a need to know person.

"Everyone knows I take care of my own," he answered. She narrowed her eyes at him.

"I'm not one of your gangster friends," she replied. He smirked. It was true, he wasn't in the most honest of businesses, and she was the only one who didn't really seem to care.

"You'll be safe if you're here…" he left off the end of his sentence. With me.

"I didn't know my life was in some impending danger," she retorted.

"It's not," he shrugged. "But instead of wondering when your next job is, or if you're going to eat next month, you could have a steady life here." With me. He had to stop that.

"You forget that I'm as well off as you," she reminded him. He hadn't forgotten. It was one of her charms. He liked that she knew the lifestyle that he indulged in.

"You don't want me here," she replied, more to herself.

"Yes, I do," he said with conviction leaning into her again. This time she didn't waver. She just glared deep into his eyes. Those looks she gave him set him on fire.

"So tell me something," he interrupted her next thought. She looked at him warily, like she was almost afraid of breaking. It hadn't occurred to him what she might be feeling. He knew that she was a master at hiding her emotions, as well as he was, but he didn't think that she was afraid like he was. He didn't think that she was afraid of being broken. If could never forgive himself if he ever broke her.

"If you are so satisfied with your life as a flapper," he mused, "why are you here all the time?" She blanched. There it was. "You could be traveling with all your new found savings and new inheritance. You could move to Manhattan or get your own show. Why are you sitting alone at the bar with a," he smirked at her, "gangster." He annunciated the last word with clarity.

"I don't know," she said softly after a hesitation. He studied her for a second. He definitely had misjudged her.

After the moment where she had caught him off gaurd, he realized he was sitting alone. She had left in a hurry. He didn't know how he felt about that. He knew why people ran. People ran mainly when they were afraid. He knew why he ran. He would run when he was afraid of letting people get too close. He wasn't used to unconditional love and he didn't even think that was what this was. It was… inevitability.

She knew this place. As successful as it was during the day, it simply thrived at night. That was strange considering only the people with questionable nature came out at night. She couldn't count the number of times she had seen him making deals around this hour.

So why was she here? He was right when he asked her why she came here all the time. She simply didn't know. He would use words like "inevitable" and "amazing." (She didn't think he could really be talking about here, though. That didn't seem like it described her.)

But the real reason, she was beginning to realize, that she kept coming back wasn't for the performances or high quality bootlegged booze (because no one could import the good stuff like he could.) It was for him. That heinous, nauseating, playboy of a gangster was why she kept coming back time after time.

She had never felt anything like she had felt when she was with him. He made her feel desired and needed. But she supposed that was how he made all those girls feel. And then he would kick them out of his bed just as fast.

She didn't like being used. She had enough of it when her seemingly perfect boyfriend had cheated on her with some leggy blonde. She didn't want to be broken again, but that seemed like a high possibility whenever she was with him.

He was a beautiful specimen. He had hard angles to his face that didn't seem attractive at first, but when you were around him more and more you realized that he was just gorgeous. His distinctive nose, distinguished eye brows, leering, slanting, exotic eyes were just the beginning. It was his smug smirk that always seemed to pull her in. He looked at her like he had known her for lifetimes. She couldn't help but feeling the same way when she looked into his dangerous dark eyes that so matched her own.

He knew too much. He was too knowledgeable about her. She didn't like it. She was supposed to be perfect and put together. Somehow he brought the wildness out in her.

She didn't used to be a flapper. But she arrived in Chicago and everything was so different from where she was from. The liquor and jazz was exhilarating. She found friends here and she was pulled into a world that was different, but sort of similar to something that she couldn't place.

Then she met him. She could pick him immediately out in the crowd. He just had a presence. The crowd would part for him like the Red Sea and she knew he was important. He wasn't important just because he had money and power. He was important because he was special. She saw something in him that she shouldn't have. He came off as a self absorbed jerk, but there was something so similar in him to her that she couldn't let him go.

That was probably a bad idea. But she found that all of her logical decision making skills vanished whenever she was ever in the slightest proximity of him. He had an effect on her that she couldn't push away like other men.

She could make men feel inadequate and small with the slightest look. But he never backed down. In fact, whenever she demeaned him, he seemed to be provoked. More and more, she was thinking about how he was her perfect match in every way. Yes, that was definitely a bad idea.

When he approached her that night, she had already seen him. He was hard to miss, obviously. But she knew she had to protect herself. She was just another girl to him, another fun time. She was done with men treating her in that fashion.

She rebuffed him in the only way she knew how. She insulted him with barbed banter about how his outfit was ostentatious and how it seemed utterly ridiculous that he ever found time to run a business with all the drunken blonde women who seemed to fall into his lap.

She ignored the attraction she felt for him and the electricity she felt when he gave her that leering look, and just walked away. She thought she had rid of him, no matter what sort of appeal he held for her. She was wrong.

He came by that joint every day, just watching her. She made a decision that he was completely creepy. And it seemed strange how he actually seemed to enjoy their conversations. He liked to battle his wit against hers (which they seemed to match blow for blow.)

He introduced himself with that smug look. He thought she had no idea who he was. That was preposterous. Of course she knew. She knew everything. But no matter how much she insulted him and through careful practiced and lovingly crafted badinage at him, he would not relent.

How she ended up at his place that night was beyond her. She was finding herself falling to his wile charms and she hated herself for it. She was falling into the same trap that every woman in Chicago was. It was disgusting.

But she couldn't help but feel treasured whenever he looked at her. She had never felt that way about anyone. Already that night, it seemed an inevitability that she would relent to him. She didn't want to admit it. She was the ice queen. Nothing broke through her façade. Nothing phased her mask except him.

It was dark then, well after midnight. She never told him this, but she really liked his place in the dark. There was a dangerous ominous quality to it that no one really understood. No one understood her like he did.

She walked up behind him. His back was to her, on the couch in the middle of the room. The table in front of him held a motionless victrola. She had seen it in motion, but not many people had. This was a boozing establishment and the only music that was usually heard was the jazz band. But then again, no one had heard him play the piano either. She didn't even think that he knew she was standing there.

He straightened immediately. He knew there was something different about tonight. He hadn't realized what it was until now. He hadn't realized what it was until her intoxicating scent had reached him.

"Why don't you take a seat," he said smugly, not bothering to face her.

"I'd rather stand," she said with superiority. He finally looked at her. The soft late night jazz filtered through the room. Few couples were dancing to the music. He rose to his feet, taking her in.

There was definitely something different about tonight. It was like the first time he saw her. There was clarity and a real quality to her that had ensnared her the first time.

She rounded the couch, standing on the edge of the floor. He found himself on his feet. She didn't like how things just happened to her. She had always been a romantic, and she knew it. She had always wanted to be swept off her feet but this was entirely different.

He was smooth, she had to admit. She didn't know how, but his hand found hers in something that felt natural. She had never shared more than a drink or a smoke with this man and he was touching her like he had known her forever.

And she let him. His breath brushed gently against her cheek. It just all seemed so right. She couldn't put it together. He was all wrong. He was illegal, dark, and dangerous. He could get arrested any day for the things he was doing. She should smack him for being so forward with her. But instead, she just let him hold her. she didn't want to be without someone anymore. She didn't want to be without him anymore. She didn't want to feel lost. And that's exactly what he did to her. He made her feel whole again. She didn't feel scrutinized and studied for her next fault.

His warm hand steadied on her back. She just put her own hands on his broad shoulders, unaware of what she was supposed to do; what was supposed to happen.

"Do you have the right answer, yet?" he prodded playfully. She wanted to tell him "yes." Yes, she had never felt more alive than when he looked at her. Yes, she wanted to be here, no matter how against her morals it was. Yes, she wanted to be wrong for once. But maybe, if this was dirty and shameful, she didn't want to be right.

"You don't take no for an answer," she whispered back. It seemed like such an intimate environment that she didn't want to ruin it.

"I can be patient." Can be. He usually wasn't. But for her, he could make an exception.

"You're too arrogant for your own good," she responded lightly, connecting it to that very day. It wouldn't be a good day unless he was reprimanded by her. She reminded him 10 times a day that he was arrogant, heinous, narcissistic, and nauseating. He wouldn't have it any other way.

"Soon you'll come around to my way of thinking." His inner monologue wasn't as confident as his actual tone. They found that they were swaying comfortably to the smooth music. She didn't like how her fingers were instinctively twining in his hair at the back of his head. It felt too comfortable. She felt like she had just met him and she was falling dangerously.

"What if I didn't?" she asked.

"What?" He hoped the fear wasn't apparent in his voice.

"What if I didn't come to work for you?" she made it clearer. She was very aware of the sudden tenseness in his shoulders.

"What if I…" she continued. "What if I was just… here?"

"…Meaning?" he asked, curious. He gazed into her midnight eyes. They were so full of secrets yet they were so open and vulnerable.

"I wouldn't have to work here. I could get jobs wherever I wanted. But I could still be… here…" she stated, "with you." He couldn't break the stare. He hadn't expected this to happen. He had expected to have to use his powers of persuasion to get her to even stay an hour.

He leaned in so their cheeks were touching gently. He tried desperately not to inhale her essence. He whispered her name huskily.

"You were… amazing up there," he confided in her. She struggled to regulate her breathing. Of course she remembered. He was the only one looking at her. There was something in his wonderfully dark eyes that she couldn't place. She didn't know if it was lust or desire. Since she met him, she didn't know anything anymore.

She pulled away from their embrace. He tried his best to ignore the sudden spike in his adrenaline. If she just left him now, he didn't know what he would do. He would feel totally lost.

She pressed her lips against his. He was taken aback. He took a hesitant step backwards, taking her with him. It took all of his self control not to take her right there. They broke away from the gentle embrace. He took her silky shoulders in his hands, breathing her in.

"You sure?" She answered him with a heated kiss.

"They all used to here, back in the day. Gangsters, fighters,musicians. Dangerous folks, no doubt. But they had style. Something tells me you'd fit right in."

- Horace Rogers

--Chuck in Real Life


While editing my fics, I realized thatI forgot something when I submitted this. The only thing I added was the quote at the end. That was when Chuck was going to buy a speakeasy and the owner commented on how much Chuck was like the people who would come to the speakeasy. I thought it was fitting.