Hey everyone! :) I have to apologize for not writing GG fanfiction in awhile. This story is basically how I envisioned Chuck breaking up with Raina Thorpe. I know this happened a long time ago in the show, and I know they were never in Chicago, but I just thought it might make a worthy one-shot. Hope you enjoy! And even if you don't, reviews/critiques are always appreciated! :)


She stood on the marble staircase in a sparkling silver dress, calling out to him like a lighthouse beacon to a ship in the dark of night. Her straight black hair cascaded down her shoulders and shimmered under the bright chandelier lights, reminding him of ebony silk. When she spotted him staring up at her—for she was so self-possessed that she could sense when men were looking at her—she responded with a sparkle in her coffee-colored eyes and a red-lipped smile.

Chuck Bass was never one to quote literature, but as he gazed upon Raina Thorpe in awe, he was reminded of a book he read in his Classical History class when he was a junior at St. Jude's Academy. Of course, Chuck had no interest in classical history. He only took the course because his best friend Nate Archibald was taking it and offered the opportunity to copy homework. Chuck didn't remember the book's title or plot, but he recalled his white-haired, monotonous-voiced teacher mentioning something about a stunning Ethiopian princess whose beauty made men fall at her feet. Being Chuck Bass, he would remember that part. And as Raina began to descend the stairs, he wondered how it was possible that a person could imitate a piece of fiction so well.

"Hey," Raina said smoothly as she sauntered over to him. She noticed that he was dressed in his black suit with a burgundy undershirt and beige bowtie, one of her favorite fashion ensembles of his. She loved how he stood completely straight no matter where he was, like a royal figure constantly commanding respect. She admired his broad shoulders, and he gave her his trademark smirk as he heard her silver Louis Vuitton heels clicking with each step that she took.

They could not help but smile as they recognized that sexy confidence in one another that they knew every businessperson needed to have. In fact, they knew everything else about the business life as well: how to apply pressure to people without appearing too forceful, how to repress emotions lest they ruin business deals, and how to take power without regrets. As children and inheritors of the modern-day Rockefellers and Carnegies of New York, they both grew up in a world different from anyone else they knew. Despite the intense pressures of that world, they both fit into it extremely well, and neither would trade being a part of it for anything on earth. They returned to it again and again despite its risks, like the lab mouse returning to a piece of cheese attached to an electric wire.

Of course, Chuck also realized how greatly they both understood the pains of that world. Both he and Raina transformed into adults mentally by the age of five, since they wished to impress their fathers and prove that they could handle inheriting the business one day. They were consistently craftier and possessed more intelligent, calculating minds than other people their age. At first, their mindsets caused their peers to alienate them—for what do simple-minded children and teenagers know of the evils of the world yet?—and this resulted in a secret, social insecurity that only the brilliant truly understand. Chuck responded to this insecurity by honing his inclination to party, showcase his wealth, and drink heavily as a teenager. He hoped such actions would earn him the admiration of his peers and compensate for the qualities which made him a success in the business world but a lonely young man in the real one.

Raina understood how greatly such actions only increased problems rather than alleviated them. She also recognized the wondrous rush of adrenaline when a good bargain was made, and the heavy-hearted pain of the tears she could never cry. She understood it all, and therefore she understood him. Perhaps that was why he had to do what he was planning to do.

And perhaps that was why the silver dress that Raina wore reminded him of a different silver dress, one that someone else wore to a certain debutante ball two seemingly-long years ago.

"Are you okay?" she asked, immediately sensing his discomfort despite his smirk. "You don't seem yourself tonight."

He allowed the silence to respond for him.

"I need to talk to you," Chuck finally explained in a deep-throated whisper, "but not here."

Raina nodded solemnly, as if she had been expecting what he was going to say. Her eyes widened in the way they normally did whenever she listened to a proposal from a fellow businessman. They remained as unblinking as the eyes of the people in the portraits Chuck had seen.

"There's an outside dining area and garden that's sure to be empty," she said, looking towards the right and then back at him. Her brow seemed to lower slightly, as if to signify that her mind was switching to defense mode. Chuck motioned for her to walk ahead of him by outstretching his arm, and he was thankful she did so. Before he followed her, he grabbed some champagne off of a tray that a waiter was carrying. He knew he would need it.

When they walked outside and into the Art Institute's garden-dining area, Chuck shut the glass door behind them. The lonely aura of the empty, green tables and chairs was offset by the bright orange and yellow flowers surrounding the square area on all four sides. The sound of the rippling water in the nearby pond was peaceful, contrasting the strain on Chuck's nerves. Raina took a few steps away from him and then turned to stare him down, placing her hands on her hips as she did so. She reminded him of a sheriff in one of those Western movies that Nate's dad used to watch, poised and ready to draw her weapons.

"Alright, what is it?" she asked sharply. The muscles in her slender, stoic face tightened. Chuck stared at her for a few moments, his chocolate orbs appearing gentler than usual. He downed the rest of the champagne and placed the empty glass on a nearby green table, hoping the liquor would calm his nerves. He sighed deeply, wishing he could pull out a cigarette as well.

"Raina…I think we need to break up."

She noticed the resolute tone of his voice, and how he did not even hesitate to tell her his feelings directly. She nodded once, slowly.

"Right. And just why did you decide to tell me this now, during my father's gala?"

Unlike what many men would have done, Chuck actually considered that. He wanted to wait until tomorrow to tell her, or even the day after. Yet he knew where Raina would desire him to be after the evening was through, and as unusual as it was for him, Chuck knew he could not go through with that.

"I know this isn't the best timing, but we haven't had the chance to discuss it as of late."

He wasn't lying. All weekend, Raina accompanied her father to meetings and left Chuck to his own devices. He did not mind, however; he needed the time to think. Plus, the deep-dish pizza he tried the other night while on a solitary stroll down Michigan Avenue tasted better than okay.

After a brief pause and a small sigh, Raina looked away from him.

"Can I ask why?"

For the first time in a long time, Chuck Bass's mouth went dry. How in the world did she expect him to explain something that simply could not be explained?

"I think you're a wonderful, brilliant person," Chuck said, dodging the question. "I admire you and respect you immensely, and I am really sorry for doing this to you."

It was not the champagne talking, and he surprised himself with his sincerity. The Chuck Bass of two years ago would never have admitted such feelings to any woman he slept with.

Well, almost any woman.

"But there's someone else, isn't there?" Raina asked, without any tremor in her voice or alteration in her expression.

Only she could be so direct. Chuck nodded lamely. After what seemed to be an eternity, the chirping of a cricket killed the silence.

"Who is she?" For the first time in the conversation, Raina's stern voice became edgy.

"Who it's always been," Chuck immediately thought. He knew he needed to stop lying to himself. There was no one like Blair Waldorf, and there never would be. He did not know why he continued to search in vain.

"No one you would know," he lied. She knew completely well who it was. Raina had woken up next to him too many times to find him staring either at the hotel walls or outside of the windows, his dark eyes gleaming reflectively as he called Blair's memory to mind. She often walked in on him daydreaming when she met him for coffee or a meal, knowing that his heart's desire was not standing before him. Raina could offer him the weight of the world in gold, and it would never be enough to convince him to stay with her. As much as he hated to admit it to himself, Chuck Bass would forever remain irrepressibly in love with that brunette whose virginity he had taken in the back of his limousine two years ago.

Raina did not press him for the girl's name, for she recognized how uneasy it would make him when he was already clearly discomfited. She merely looked down at her heels and scraped one against the stone pavement, attempting to ignore the melancholic realization that she never stood a chance. She crossed her arms against her chest, as if protecting her heart once again.

"So that's it. We're done."

That was what Chuck knew he was going to miss the most. Raina was so straightforward and independent. Chuck knew too many women who would pine away in sadness after a breakup, and then call their boyfriends begging for redemption. Raina, however, knew that anyone who did not want her did not deserve her. She would be upset at their parting, certainly, but she would never waste time on someone who clearly expressed that he did not want her anymore. Chuck loved this about her, but he also knew that once a man broke up with Raina Thorpe, he was never going to receive a second chance. If he was not so certain that he would not be running back to her, Chuck would worry about that.

"Really Raina, I'm so—"

"It's alright." Being the businesswoman she was, Raina mustered a smile to convince him of the truth of her statement. Chuck did not buy what she was selling, for he recognized the sad glint in her eyes. "I knew it was going to happen sooner or later," she added poignantly.

Was it really that obvious? He chose not to ask. They basked in the silence once again, knowing that no more words were needed. Chuck was not going to attempt to appease her further, for he knew she would not have it.

"I have to go."

"Yes you do," she replied with unwavering certainty.

She would not like what he was about to do, but Chuck could not help himself. He cared about Raina too much just to walk away. He took a few steps towards her until he stood directly in front of her, as he had done many times before. Surprisingly, Raina allowed it and did not move away from him. Chuck then gently took her hand and softly brought it to his lips. It was the only correct way to say goodbye to his princess.

When he tenderly lowered her hand, she pulled it away and tucked it under her arms again. She continued to look at him, examining his face for the final time.

"Goodnight, Chuck."

"God, she is outstanding."

If only he could ever love her.

"Goodnight, Raina."

He turned his back to her, picked up the empty champagne glass off the table, and walked towards the building. He noticed her reflection staring back at him in the shining glass doors. It was a more tragically beautiful sight than any of the paintings Chuck had seen that evening.

When he closed the door behind him, Chuck wandered past the Modern Art wing and into the main hallway of the Art Institute. He suddenly felt as empty as the glass he held in his hand. The place was filled with chatty, wealthy businesspeople, yet Chuck felt lonely. Everyone else suddenly seemed to be a part of a family that he did not fit into.

His thoughts returned to Blair for what seemed to be the millionth time that evening, and he recalled how she was the sole person who could cure his loneliness. She accepted him for the person he truly was ever since they were young. She shared his outlook on life and always knew exactly what he was thinking. Blair may have not understood his business world, but she certainly understood his personal world.

"And yet, you somehow managed to lose her."

That was when Chuck realized what he always did whenever he needed to make things right: he had to return home. Chicago compared to New York was exactly how Raina compared to Blair: good to him most certainly, but not the very best.

He did not wish to see Blair immediately when he arrived in the Big Apple, for he would not know what to say to her. Their relationship had encountered so many problems that he could not resolve everything simply with an apology or expression of affection. Chuck knew it would take much effort to work his way back into Blair's good favor, but he also knew that she was worth it.

Chuck placed the champagne glass on a passing waiter's tray, and then started walking towards the exit. He caught sight of Russell Thorpe across the room, laughing and clapping the shoulder of one of his associates. Chuck knew that Raina would have to repress her feelings over what transpired tonight for her father's sake, and he empathized with her. He knew that feeling all too well.

After running outside and taking a cigarette break, Chuck whistled for a taxi. He would have taken a limo except that he arrived earlier with Raina in hers, and he could not possibly take that back to his room at the Drake Hotel. The taxi looked and smelled exactly like something his father used to warn him to stray from, lest he ruin the Bass family image. He could barely understand the heavily-accented voiced of the cab driver, and safety code for the cab had not been updated in almost twenty years. Yet Chuck did not complain, for he just felt relieved to escape.

He closed his eyes for a moment in the backseat, suddenly feeling exhausted. It was difficult to run an entire corporation and deal with true love at the tender age of nineteen. Not that Chuck could help his reaction to Blair; had he paid any attention in his classical history class, he would have known that once Cupid's arrow strikes, nothing can cure the illness it brings.

Yet when Chuck finally made it back to his hotel room and gazed out his window at the bright-lighted Michigan Avenue for the final time, he found himself most excited to return to that one lady with which his love affair would never cease: New York City.

The End