A/N: Okay, I know that you are all awaiting the present day meeting between Chuck and Blair, but this flashback was too important to skimp on, so the entire chapter is one long flashback. I promise that there are only a handful of necessary flashbacks left and soon it'll all be present day angst.
Chapter 5
November 2014
It was unseasonably warm for mid-November: the sun was shining brightly, and the temperature was set to reach a high of 73. As the leaves floated to the ground around him, Chuck guided Monkey through the park; for once, he gave himself the opportunity to enjoy the moment and take in the beauty that is autumn in New York.
He was uncharacteristically chipper for a Friday evening after a long work week, but, having just received confirmation that Bart was finally naming him as COO of Bass Industries after months of cancellations and delays, he couldn't find a single reason to sulk.
Monkey seemed to sense the change in his owner, giving into his canine desires to bark at birds, chase squirrels, and urinate on every tree they encountered. Normally Chuck would try to correct such behavior, but today he just couldn't bring himself to care. If Monkey wanted to act like a dog, who was he to inhibit his natural instincts?
As he steered his dog around a pre-teen on a skateboard, his phone buzzed in his jacket pocket. A smirk spread across his face when he read the text from Caroline congratulating him on the official announcement.
He immediately tapped back a response: 'Does this mean that you will finally let me take you out for drinks? You know, to celebrate?'
After he left California in June, he couldn't get the model out of his head. There was something about her, about her response to him, that made him yearn to pursue her. At first, he thought it was the sting of rejection and the thrill of the chase, but he soon realized that it was something more – he was drawn to her in a way that he hadn't been drawn to a woman since his unhealthy obsession with a certain Upper East Sider.
In August, he'd called Serena to set up another visit, and she was ecstatic to have her friends in her city again so soon. Of course, he didn't tell her that he had ulterior motives, but he sought out Caroline at every turn. On his last night, he finally found her and through calculated precision, he made sure that she was aware of his presence without approaching her. He hoped she'd realize that he was taking her advice, letting her come to him. And after several hours of anticipation, she did just that.
He was surprised to find that the night didn't end in explosive orgasms tangled in the sheets of his hotel room bed. It ended with good conversation and a hug; somehow their strange dynamic blossomed into the beginnings of a true friendship.
It wasn't that he didn't want to sleep with her; he did – desperately, but it wasn't his central focus when they were together. Between September and October, he flew to L.A. twice, no longer under the guise of visiting Serena, to spend time with Caroline. She was well aware that he was attracted to her, that all she had to do was say the word and he would pounce on her, but she was content with the platonic status of their relationship. They flirted through text, his innuendos bordering on inappropriate, but to this day, five months after meeting her, he'd yet to even kiss her.
He anxiously watched the three dots indicating that she was typing a response jump around in anticipation, not paying a bit of attention to where he was walking, when he tripped over Monkey who'd stopped dead in his tracks to sniff a pair of high-heeled pumps. Chuck stumbled forward, colliding with the owner of the shoes. When he looked up to offer a half-hearted apology on behalf of his distracted dog, his heart jumped into his throat at the woman standing in front of him.
Over the past year and a half, he'd actively avoided her at all costs. Sure, they'd been invited to the same events, but the moment he laid eyes on her from across the room, he'd excuse himself to the restroom, call Arthur, and leave through a side entrance. He had yet to bring himself to face her, his body electrified just being in the same room as her. To her credit, she seemed to heed his plea to let him go. Even when they were in close proximity, she always cut her eyes away and never tried to speak to him. He found himself torn on her response: on one hand, he was grateful. She had done as he'd asked, and he appreciated the fact that she seemed to respect him enough to leave him be. The less logical, more emotional side of him, though, wished she had continued to fight for him, to show him that he meant something to her and that she wouldn't give up on him so easily.
He knew that his contradictory reactions to her distance were both unfair and nonsensical. He'd moved on and found happiness without her – or at least he was trying to. There was no reason for them to interact; exes have no place in each other's lives, and they were both better off without each other. He convinced himself that these unreasonable hopes were products of nostalgia and familiarity. He'd wanted her out of his life, and now that she was willing to concede to that request, he had to find a way to let go of her memory.
Now as he stared at her wordlessly, her eyes grew large, waiting quietly for him to speak, almost as if she was afraid to say the wrong thing. Almost as if she expected him to scream at her. He winced at the memory, his tone of voice, the way tears had trailed down her cheeks when he berated her and told her that her love wasn't enough. His anger had made him impervious to her tears, but now, with the image playing in his mind, knots of guilt tied themselves together in his stomach.
He shook himself free of those thoughts and offered her a smile. "Hey," was the only greeting he could force through the lump constricting his airways.
"Hi," she spoke softly, returning his smile with a tentative one of her own.
Their eyes remained focused on each other, neither one moving as several beats passed between them.
"It's been a while," Chuck finally observed awkwardly, mentally chiding himself for the stupidity of such an obvious statement.
"Yeah," she nodded, emotion flickering across her face, "How've you been?"
"Great actually," he answered, pulling Monkey's leash more tightly as a poodle marched by them. "Staying busy."
Blair looked down at her shoes, swallowing the painful realization that they were engaging in uncomfortable small talk – like two strangers who didn't know how to talk to each other. "I saw that you were promoted to COO." His heart pounded when he recognized genuine pride beaming behind her eyes. "Congratulations."
"Thank you," he replied earnestly.
She nodded, sadness settling into each of her features. She was still so beautiful, but he couldn't help but notice the wariness outlining her eyes. "Well," she said, "I'll let you and Monkey get back to your walk." Her hand reached out and gently scratched the dog's head as if she would never have the chance again. "It was nice seeing you, Chuck."
She turned in the opposite direction when he didn't respond, and his heart clenched at the sight of her walking away from him. Before he could stop himself, he called out, "Wait."
She paused, looking back over her shoulder, unsure if she had heard him correctly.
He jogged to catch up to her once again, Monkey trailing happily alongside him. "I don't want to leave things like this. We're not strangers."
Relief flooded her body and, this time, a true smile, free of the previous sadness that had melted into the corners of her lips, spread across her face. "No, we're not strangers," she repeated in agreement.
"Come on," he motioned for her to follow him, "If you don't have anywhere you have to be, let me walk you back to your house. Give us a chance to catch up."
"I'd like that," her eyes glistened with renewed hope.
Chuck returned the cell phone that was still lodged in his right hand to his jacket pocket without a second thought.
As they walked toward the Waldorf penthouse, they kept the conversation light, discussing such topics as Blair's grudge against her new mailman, Chuck's new working relationship with Bart, and Eleanor's shocking announcement that she planned to retire and name Blair the head of Waldorf Designs. They laughed and within minutes fell into a natural rhythm of conversation and banter.
The ethereal quality of a spring-like day in the middle of November seemed to stretch into their fortuitous meeting, like there was some hidden symbolism behind it that neither one understood. To the outside observer, they were two friends who shared the closest of bonds; years of hurt feelings and broken hearts didn't exist between them. But all too soon, they were standing outside of Blair's building, teetering on the brink of a final goodbye.
Chuck looked up at the familiar building before shoving his hands into his coat pocket, Monkey's leash looped around his wrist. Once again, he found himself at a crossroads. Did he take this random encounter as the universe providing him closure, or did he perhaps consider it as fate offering him a second chance to right the mistakes of his past? Had enough time passed that he and Blair could at least be friends again? He almost asked her if he could see her again, if maybe she wanted to have dinner soon, but the words lodged in his throat. Instead, he stood there dumbly, rocking back and forth on his heels, unable to will his body in either direction.
Similarly, Blair seemed to be contemplating her next move. She shifted her bag on her arm, rummaging through it for her keys but never actually making contact with them. Her hands busied themselves with the search, but her head was elsewhere, overcome with anxiety that this might be the last time she has him like this, the last time he looks at her with something other than pain and hatred reflecting in his eyes.
So ultimately, she was the one who took a chance and made herself vulnerable. "There's still left over birthday cake -" Her throat was dry as she forced the words out, "I can't possibly eat it myself. Would you like to -" She motioned toward the door, dropping her words at the obvious implication of her gesture.
He arched his eyebrows and asked, "White chocolate with raspberry ganache?"
"Is there anything else?" she returned, biting her lip at his playfulness.
He followed her to the penthouse, leaning against the inside wall of the elevator as they slowly ascended to the top floor. His heart beat erratically against his rib cage, second guessing every decision he made. How many times had he ridden in this elevator? How many times had he kissed her here, whispered naughty words against the shell of her ear, snaked his hand up her skirt just to get a reaction out of her? Now, though, what was he doing? He didn't belong here anymore.
When he risked a glance in her direction and she looked up at him from under dark lashes, a sweet smile pulling at the corners of her pouty lips, he no longer cared if he should be there or not: it was the only place he wanted to be.
The elevator doors finally opened to the penthouse, and Chuck inhaled sharply at the surreal feeling of standing in her foyer after so many years. The breath was knocked from his lungs as the memories hit too quickly for him to register; images flashed through his mind, but he only caught glimpses before each one was replaced with a new memory.
Blair furrowed her brows in confusion. "Are you okay?"
He cleared his throat to push away the intrusive reminders of the life he used to live. "Yeah, there are just a lot of memories here."
"Good memories, I hope."
"Great memories," he admitted, fixing his eyes to hers, suppressing the equally vivid memories of arguments, break-ups, and heartache.
She looked down, her pulse jumping in her throat nervously. "Some of my favorite memories include you."
She couldn't bring herself to look at him, to gauge his reaction to her confession, but she could hear the unsteady exhalation he let out before changing the subject.
"About that cake?" he gruffed, his voice thick.
"Right," she let out a sheepish laugh, leading him into the kitchen.
With shaky hands, she served them each a slice of her favorite cake and settled herself onto the bar stool next to him. Monkey curled up into a ball under their feet, exhausted from their longer-than-normal walk. The silence between them no longer felt awkward, and there was no need to fill it with meaningless small talk. They had slowly fallen back into a comfortable camaraderie where the conversation ebbed and flowed naturally.
She watched Chuck hunch forward with terrible posture, resting his elbow on the counter as he shoveled forkfuls of cake into his mouth. Typically, his manners were unmatched, but this lax conduct, she realized, was a sign of his comfort level. Her heart clenched at the notion that he still belonged here after all this time, and she found herself longing for this – for a relaxed, ill-mannered Chuck and a calorific dessert – to be her new 'normal.' There was nothing she yearned for more than a lazy Monday evening with this man and his dog.
"Delicious," he commented, pushing his plate away from him. "Happy late birthday, by the way."
"Thanks," she acknowledged, moving their plates to the sink while Chuck helped himself to the liquor cabinet, pouring two glasses of champagne. "What are you doing?" she asked.
"A toast," he explained, as if everything about this moment was entirely normal. Neither one wanted to face the reality staring down at them, so they both went on pretending that nothing was amiss. "Twenty-four looks good on you."
"And -" she raised her glass to meet his, "A toast to your promotion. I'm proud of you, Bass."
Her words struck him in his chest, piercing straight to his heart. He pressed himself a smidge closer, shrinking the space between them to less than a foot. After downing the champagne, he left his flute abandoned on the countertop next to him and drew a slow breath.
"Listen, Blair," he rasped, the tone of his voice catching her off guard. She waited, but he couldn't find the words to express what he wanted to say. Too much had happened since he last spoke to her, and there was nothing left for either one of them to say.
She blinked, reality finally washing over her. They weren't playing make believe anymore. This whole day was nothing but a fluke that the universe threw at them out of boredom. Soon enough, he would leave, and she'd be alone once again.
"I've missed you," she whispered, tears pooling in her eyes, her lower lip quivering under the weight of her confession. She was desperate to keep him there in this moment, to cling to whatever sliver of hope their renewed companionship had forged. "I've missed you so much."
Chuck swallowed hard, his chest swelling painfully from the sudden onslaught of emotions. He wasn't sure if he could find it in himself to offer her forgiveness that she had yet to seek out, but he wasn't ready to walk away from her again, either.
Cautiously, he reached his hand up, just barely allowing his thumb to brush away the lone tear trailing down her cheek. When her eyes met his, he was hopeless to fight the truth. On a ragged breath, he murmured softly, "I've missed you, too."
"Chuck -" she let out a quiet sob, his name a singular plea for him to make promises he wasn't capable of keeping.
The desperation in her voice, his name on her lips broke something inside of him, and he closed the distance between them, pulling her into his arms, wrapping them tightly around her waist. Her head fell to his chest, her tears melting into the fabric of his dress shirt as he subconsciously soothed circles into her back with the palm of his hand. His chin rested atop her head, letting her cry until there were no tears left.
They stood that way for some time, until slowly Blair lifted her head. He flinched when her temple brushed his cheek, but he didn't pull away. Driven on by instinct, she raised her hands to cup either side of his face, testing his reaction to her touch. When he didn't move, she pushed herself to the balls of her feet and pressed a soft kiss to the side of his jaw – innocent and chaste, just to see if he would let her.
His hands tensed at her waist, but he remained otherwise motionless. He didn't speak, but the fire in his eyes matched the one burning in her chest. With new resolve, she pressed her lips to his, gentle and patient, letting him decide how much he would allow. His eyes closed, and his lips parted slightly as his body relaxed into hers. It was all the permission she needed, so she deepened the kiss, sliding her tongue over his bottom lip.
He groaned, grasping her hips and lifting her onto the counter top. She whimpered, opening her legs to accept his body between her thighs. Her hands tangled in his hair, his mouth frantically peppering kisses down her neck and across her collarbone. His more carnal desires took control, and he yanked her skirt up to pool around her hips, pressing himself into her until she could feel him throbbing against her thigh. He palmed her breasts through the thin material of her blouse as her fingers worked the buttons of his shirt. Her nipples pebbled beneath his fingertips, and she arched her back, stretching her arms behind her to give him better access. She let out a loud squeal of surprise when her hand landed on the forgotten cake platter, coating her fingers in frosting.
Chuck startled at her shriek, and he immediately forced himself away from her. Panting, he offered her a napkin and lowered her skirt over her legs. He backed up several steps, putting distance between their bodies. Closing his eyes, he sank back against the wall and rasped out, "I'm sorry."
She dropped down from the countertop after cleaning off her hand, once again closing the space between them. "Don't be," she whispered, pressing her lips to his neck and kissing a path to his jaw. "I'm not."
He inhaled sharply, pushing her back by the shoulders so that he could think. "I can't do this, Blair."
"But you said -" her lip jutted into a pout, tears of rejection stinging in her eyes.
"I have missed you," he tried to assure her. "But I'm not ready."
"It's been almost two years," she protested, her voice breaking on the last word.
"I'm moving to California," he confessed quietly. "It was one of the conditions of my promotion - to oversee the West Coast branch."
Her mouth fell open, and she closed her eyes, giving herself a moment to gain her bearings. Fate was so cruel. "W-when?" she stuttered.
"The first of the year." He reached for her hand, wishing with everything in him that circumstances were different. Regret marred his features when he added, "I won't start something I can't finish, Blair."
She smiled through the tears, lifting his hand to her lips. "Just give me tonight."
"I can't make you any promises. Things are really complicated right now."
"I'm not expecting anything from you, Chuck," she looped her arms over his neck, hoping to quell his fears. "One more night – the proper goodbye that we never got to say."
He relented, his body needing her more than his mind could fathom. She laced their fingers together, leading him to her bedroom, her heart beating hard in her chest with emotions that she couldn't express.
XOXO
The next morning, she awoke to a pair of strong arms wrapped around her waist. The entire night had been a bittersweet expression of penitence and forgotten love; she tried to force the knowledge of his imminent departure to the back of her mind, but it was always there, silently taunting her temporary happiness.
She rolled over to face him, tracing her finger slowly from his temple down the ridge of his nose and over the arch of his lips, carefully memorizing each and every detail. His eyes fluttered open, and he smiled softly, pulling her in for a gentle kiss.
"Can you postpone your move?" she asked hopefully. "Or better yet, tell Bart he can suck it; you're not going," she added with a soft laugh.
The circles that Chuck's fingers were drawing against her shoulder stopped, and his jaw flexed from her ill-timed joke. "Bart's sick," he said quietly. "They say it's terminal, but there's a doctor in L.A. who some say is a miracle worker."
"Oh, God," her mouth flew open, her heart breaking all over again for him, "I'm so sorry, Chuck."
He softened, his hands continuing their exploration down her side to rest against her hips. "Our relationship is stronger than it's ever been, and -" he blinked away the traitorous tears trying to form behind his eyes, "It might be a wasted effort, but I have to try, you know?"
"I know," she whispered, pulling him closer so that she could kiss his temple. "I know."
"That's why I can't start anything with you now, Blair," he rolled over onto his back, their previous face-to-face position too intimate for this conversation. "I've got too much on my plate, and I haven't even had time to figure out where my head's at. I'm not in a good place for…I didn't expect this to -"
"You don't have to explain," she soothed. "It's okay. I understand."
"Maybe one day -" He stopped himself from making another promise that he wouldn't be able to keep. "This has been nice." She arched her eyebrows, causing him to laugh. "Not just the sex, although it was pretty damn amazing. But everything else, talking to you, being around you again. I needed that." He pressed a kiss to the palm of her hand, lacing their fingers together.
"You know that's never going to change, right?" She rested her head on his chest, finding comfort in the steady rhythm of his heartbeat. "I'll always be here for you no matter what – if you need to talk, need a friend, I'm here."
"I have to go soon." He rolled over, positioning himself over top of her. Pressing gently into her, he groaned as the warmth of her body engulfed him, and he whispered, "Let's make the most of the time we have left."
She moaned softly as her body became reacquainted with his for a second time. Each of his thrusts, each of her kisses spoke the words neither one of them were brave enough to speak aloud. Their emotions were still too raw, their impending separation too near, so they poured everything they had into each other, shutting out the rest of the world for a little while longer.
An hour later, after he dressed and exited the building with Monkey in tow, he checked his phone for the first time in twelve hours. His chest tightened at the forgotten text message waiting in his inbox.
Caroline: It's a date. :) I'll be in New York for a photoshoot in December. Can't wait to see you.
A/N: So many of you in your reviews talked about how unlikely it is that Chuck and Blair hadn't seen each other in five years while they both still live in the city, and you were absolutely right. Notice that in the last chapter Nate and Serena were unsure of when and how much contact Chuck and Blair had had since their falling out, and Caroline is under the impression that he hasn't seen her at all in five years. If anything seems confusing, I'm happy to answer questions that don't lead to future spoilers.