Chapter 2

August 2012 - Rome

She'd done it. She'd actually spent the whole summer with Dan in Rome; she'd put her relationship first. She'd needed to prove to Dan - and to herself - that this relationship was her priority above everything else, that she wasn't running from her past the way Serena suggested. Her commitment to Dan was the most important thing in her life; one may think that she was too focused on Dan, trying too hard to make it work, forcing herself to be the dutiful girlfriend of the tortured writer. But, of course, they would be wrong. For the first time in her life, she was making the mature decision to put someone else's needs before her own, and right now, Dan needed her to be a sounding board, to listen to him blather about his book, to encourage him and stroke his fragile ego whenever he was too hard on himself.

She never realized that Italy could be so boring, so pointless and repetitive. All of the food and culture couldn't make the summer pass any quicker, and the shopping was far less appealing with no one but Humphrey to accompany her. Not only were his opinions on fashion useless, but he spent nearly every outing complaining about writer's block or prattling on about the other dull writers in the program. She missed Serena. Spending the summer abroad two years earlier had been immensely more enjoyable, and that was surprising given the year that led to their time in France.

Her down time - and there was a lot of it - was mostly spent reading, or at least trying to when Dan wasn't interrupting her by grumbling over his ongoing inability to write a single sentence. In the stillness of the night, when she would slip out of bed, her mind would wander.

She hadn't spoken to Chuck since he'd found a way to help his father stay in town. She hoped he was doing okay, but she had to focus on Dan, she reminded herself. It was important that he trust her. She'd helped Chuck enough, and now she had no reason to get involved. She could pretend like they were friends, the way she had in the past, but that was a slippery slope. Her only possible avenue for self-preservation was to abstain from all contact with her ex-boyfriend.

Questioning Serena would set off a barrage of accusations about her still having feelings for Chuck. Maybe she could ask Nate how he's doing without setting off alarm bells.

Sometimes, after a few glasses of wine, she allowed her mind to run rampant. She thought about what Rome would be like with Chuck, about the what-could've-beens of their wasted summer in Tuscany. Whenever Dan touched her, and she pretended to be asleep, she recalled her summer of passion with Chuck before freshman year. She would never admit it to anyone, but sometimes her body craved someone else entirely.

In the light of the morning, her stomach tied itself into knots of guilt and dread. She and her boyfriend weren't necessarily the most physically compatible pair, but they could certainly hold the most enthralling conversation about literature and cinema.

Well, if she was honest with herself, even that - the very basis on which their relationship seemed to be founded – had been lackluster lately with Dan's focus on writing and her incessant boredom.

"Uh, Blair?" Dan's voice cut into her thoughts as he reached over to grasp her hand in his. She resisted the urge to pull back when his clammy palm made contact with her freshly manicured fingers.

She plastered on a smile. "Yes?"

"Did you hear what I said?"

"Hmm," she refused to admit that she had a habit of tuning him out.

"I said," he emphasized in irritation, "The summer's been great, and I'm so glad that you came with me."

"Me, too," she lied through her forced grin.

"I think it's really given us time to grow as a couple."

She scrunched her nose into a grimace. The only growth they'd experienced during the past two months was in the space between their bodies in bed. She was one more restless night away from kicking him to the couch. Instead of dignifying his comment with a response, she said, "I'm ready to get back to New York."

"That's, uh, what I wanted to talk to you about."

She pressed her lips together, arching her eyebrows, waiting for him to continue.

Finally he said, "So, like I said, we've had a great summer together, and I don't want to lose that when we get back home."

"What are you talking about?" she asked impatiently. He always seemed to take forever to get to the point in any conversation.

"Well, Chuck's in New York -"

"And?"

"I mean, things have been so good, and I don't want any issues like we had before we left…"

She sighed, "Chuck's in New York where he's always been, and so is Serena. I don't see what your point is. I told you - repeatedly, I might add - that you don't have anything to worry about. I think I proved that much by coming to Italy with you when, honestly, I wanted to spend the summer working on myself, setting the direction for my future instead of just tagging along while you worked on yours."

"Whoa," he held up his hands in disbelief. "I thought you wanted to come with me?"

"Well, you thought wrong," she pushed herself up from her position on the bed, crossing the room to put some distance between them.

"You told me you wanted to be here."

"And why do you think I did that, Dan?" Her voice grew shriller with exasperation.

"I don't know, Blair, but honesty, trust, and communication seem to be a central issue in this relationship, so, please, enlighten me."

"Maybe because I felt pressured!" Her eyes widened when the truth finally came out.

Dan dropped back onto the bed, inhaling sharply while running his hands over his face. He lowered his voice slightly, attempting in vain to understand his girlfriend's sudden change in demeanor, "How did you feel pressured?"

"Think about it," Blair drew a breath to maintain her composure, "You told me you loved me, you followed me to the brothel because you didn't trust me, you lied about not getting into the program just so I wouldn't be alone in the city with Chuck – which is laughable considering there are eight million other people in New York. What other choice did I have than to come with you?"

"I -" For once Dan was speechless.

"I know that you didn't mean to pressure me, but I've felt like I'm suffocating. You haven't let me breathe in months."

"When we're back, it'll be different. We've proven that we work as a couple," he tried to reason.

"No, Dan, it won't be different," she explained calmly, her decision already made. "It'll be exactly the same because I can't give you what you want."

"What is it you think I want, Blair?" he asked desperately. "I just want you. I love you."

She winced when he uttered those three words for the third time. "That right there is the problem. You've been a great friend to me -"

"Don't do that -"

Her expression softened. "But I don't - I can't - love you. We gave it a shot, but we don't work - not really. We're too fundamentally different."

"Is this about Chuck?"

"This has nothing to do with Chuck," she denied. "This is about me and what I want. I've been lying to myself for far too long, and I dragged you into that lie. For that, I'm sorry, but this just isn't going to work anymore."

Within two hours, her bags were packed and she was on a first class flight back to New York. Her heart pounded with excitement; it had been an hellacious summer, but she finally saw the light. She knew what she wanted, and she was going to get it.

Or so she thought.

XOXO

August 2012 - New York

Two months. Two fucking months since his own father cut him out of his company, out of his rightful place at his side, and he had nothing to show for it. He would've happily ceded his place at the helm, if only his father would've included him as a partner - an equal. But he should've learned from history – Bart Bass has never found even the smallest fragment of worth in his son, and nothing could change that.

Bart was right. To be a great man he had to be cold; emotions were nothing but a weakness, and Blair had broken him, bent him into a nearly unrecognizable version of his former self.

Bart's taunting words continued to echo in his mind: "You didn't try and trade her for a hotel deed? You didn't let everything fall apart when you ran away from her all the way to Europe? You didn't just three months ago almost bankrupt yourself trying to get her out of her marriage? I had hoped you had outgrown such foolish behavior, but you're still willing to throw everything away for a girl who's done nothing but toy with you."

It had been years since he'd even been in a relationship with Blair, yet, still, his every move was controlled by his feelings for her. He let her drag him around like a little rag doll, there when she needed some entertainment before being discarded without a thought.

He lifted his scotch to his lips while Monkey stared at him in disapproval. This seemed to be their routine as of late, and it always ended the same way – with Chuck passed out on the floor after drinking himself into a stupor.

He had really believed Blair before the wreck; he thought, finally, they were going to spend their lives together and forget everything society told them they should be. He let out a humorless laugh into the darkness of the suite at the thought that their love could've been strong enough to conquer everything stacked against them.Even her shutting him out after the wreck wasn't enough – he had to torture both of them by crashing the wedding, by begging her not to marry another man. At the time, it felt like fate, but, now, it felt like a pathetic and embarrassing display of desperation.

And, yet, it continued until he paid her dowry just so that she could make a mockery of him and kiss Dan Humphrey in his own fucking bedroom. Nothing could've prepared him for Blair to choose Humphrey over him – for her to galavant off to Rome with him. Quite frankly, it was insulting. He often wondered if they laughed at what they had turned Chuck Bass into.

The power that she held over him was his greatest weakness and his greatest point of shame. Bart was an asshole, but, predictably, he saw his son for exactly what he is.

His vision blurred as he poured another glass and sank onto the couch, but no matter how much he drank, he couldn't quieten his mind. Bart continued to mock him: Bass industries needs to be run by a man, not a boy.

You've never grown up.

The most you've done is use my money to redecorate.

You failed.

Rage boiled in the pit of Chuck's stomach, and he let out a growl of frustration as he hurled his tumbler toward the wall, watching the amber liquid pool on the floor around the shattered glass.

"Chuck?" A soft, startled voice called into the darkness.

Now, he was hearing things; she haunted him even in his waking hours. Her voice was a constant reminder of his unending failures – of the ways he'd failed her and himself.

"Chuck?" she spoke again, this time her apparition materializing in front of him. "What happened?"

He blinked, barely registering that this may, in fact, actually be the real Blair standing in front of him instead of some conjuration of his imagination.

"Why are you here?" he slurred.

"Because it's time I was honest with you. I love you. I'm in love with you."

She stared in confusion as he stumbled to his feet, narrowing his eyes at her and letting out a low, chilling laugh that sent a shiver down her spine.

"I have tried to kill it, to run away from it, but I can't, and I don't want to anymore."

"So what?" he snapped, his tone dripping with derision.

He staggered to the bar and pulled a bottle of whiskey straight from the cabinet, not bothering with a glass this time. In hindsight, years later, she would always regret pushing him in this state of mind, but at the time, she thought that it was her last chance to lay it all on the line – to tell him what was actually in her heart. She was desperate for some way to show him how wrong she had been.

"Now," she stuttered with an uncharacteristic timidity, "We can be together; isn't that what you want?"

His expression terrified her; she hadn't seen this side of Chuck since senior year when he taunted her love confession at Victrola. This Chuck was the worst kind of dangerous, and this time, she didn't know how to pull him out of the darkness. "It was," he scoffed, "Before I lost everything."

"Bass Industries isn't everything," she tried to reason, but she realized later that this conversation was about so much more than his position in his father's company. It was so much deeper and more complicated than she could've fathomed at the time. Her next statement was so selfish and insensitive that she would always regret her words: "I'm going to take over my mother's company, and it can be our future."

"The only reason Waldorf Designs has a future is because I gave mine up for it." She winced as the truth behind his words hit her square in the chest. "My father was right. I always put you first, and you bet against me every time." He sank back onto the couch, his entire demeanor outlined in the defeat that he felt in every inch of his tired body. "Now I have nothing."

"You have me," she said meekly, tears springing to her eyes.

He finally looked up at her, his eyes were colder and emptier than she'd ever seen them. "Yeah, until things get too hard, or you find someone better or you decide that we're better off apart, or whatever other bullshit reason you'll find to leave." His tone was laced with unyielding cruelty when he added, "Let me make it easy for you, Blair. Leave now. Before I have security throw you out. You aren't welcome here anymore."

XOXO

"You should've seen him, S," Blair sobbed into the phone as soon as Serena picked up.

"Blair?"

"Chuck's not -" She sniffled. "Chuck."

Serena let out a long sigh, "What did you expect, Blair?"

Swiping roughly at the unrelenting tears tumbling down her cheeks, she asked, "What do you mean?"

"You can't play with someone's emotions, especially someone as emotionally vulnerable as Chuck, and expect things to be okay."

"That's not what -"

"Yes," Serena's voice was stern, "That's exactly what happened. You did this to him."

"This is not my fault," Blair protested, her chest ready to burst open at any moment.

"Think about it, Blair. You were going to run away together, he was going to raise your baby, and then you cut him out with no explanation. You then confess your love to him at your own wedding and marry the other guy anyway right in front of him. And, then, if that's not enough, you convince him that the two of you can't be together until you can do it as equals, but in the meantime, you jump into a relationship with Dan – which I'm still angry about by the way, just so you know."

"I -"

"Let me finish," Serena cut in angrily, "After all of that, you abandon Chuck to run off to Rome with your boyfriend when he's facing one of the most difficult, most life-altering moments of his life. He's barely keeping his head above water, and then you have the audacity to come back and tell him that, never mind, you made a mistake, you two actually CAN be together after all. And you expect him to be okay with that? To just accept it and be able to move on?"

"I didn't think -"

"That's the problem, Blair," Serena's voice shook, and she too was crying now, "You never think about anyone else. You didn't think about me when you kissed Dan while my grandmother was dying, and you sure as hell didn't think about Chuck's feelings when you went to him with the expectation that he would drop to his feet in gratitude and welcome you back with open arms. You're selfish, Blair. At your core, that's all you are - a selfish, entitled brat, and Chuck deserves better."

Before she could respond, the line went dead on the other end. Blair's lip trembled as she stared at her phone in disbelief.

XOXO

"Thanks for meeting me," Blair greeted Nate at their favorite coffee shop a few days later.

"So, how was Italy?" he asked as they settled into a booth in the back of the cafe.

She let out a wry chuckle. "Horrible."

"Color me surprised," Nate said before he could stop himself, "Sorry."

"Why do you say that?" Blair asked gently, grateful that at least one of her friends was talking to her.

"Anyone could see from the get-go of your relationship that you were running from your feelings for Chuck."

She closed her eyes; it must've been obvious to everyone but her if even Nate noticed.

"Well, Dan and I broke up."

"Ah," Nate took a sip from his coffee, "And you're here to check on Chuck."

"I've already seen Chuck," she admitted, sadness seeping into her tone. "He's not in good shape."

"No, he's not," Nate agreed with a shake of his head. "I try to stop by every couple of days, but it's kind of useless at this point. I'm not sure what to do. I'm thinking about trying to talk to Bart - see if he can get him in for involuntary rehab or something. I'm afraid of what he's going to do to himself. This isn't like last time."

"How's it different than any of his other spirals?" she questioned quietly, not entirely sure that she wanted to hear Nate's response.

"Because last time, you were the one who could pull him out, you were his voice of reason."

She swallowed hard, several more tears adding to the record amount she'd cried in the past few days. "I want to help him."

"Honestly, Blair," Nate spoke firmly but gently, "I say this with nothing but love and respect for both you and Chuck, I think it's best that you leave him alone this time. Please don't take this the wrong way." He reached across the table to place his hand on top of hers, "But I think you've caused enough damage this time around. He won't be able to handle much more."

XOXO

Present Day

It was the first Tuesday of the month, so that meant that Blair had a standing date. She pulled on the Tom Ford dress she'd bought weeks ago but had yet to find a reason to wear it before slipping into her favorite pair of Valentino pumps. She took extra time applying her make-up and curling her hair, as if the man at the restaurant was someone she desperately needed to impress.

"Hey, Blair," Nate greeted as she slid into the seat on the opposite side of him. "You look beautiful tonight."

"Thanks," she smiled sweetly at one of her oldest friends. One of your only friends, her mind amended.

They placed their orders with the waiter and chit-chatted about their week. Nate regaled her with stories of his disastrous first date with a young journalist, who was secretly seeking out intel on his family, and Blair was happy to listen to him. When he asked her how life was, she didn't have much to share besides a couple of mishaps at the atelier and a strange run-in with Georgina at Saks.

Finally, she couldn't let the unspoken words linger in the air any longer, so she broke the only rule of their monthly dates: There was to be no mention of Serena, Chuck, or Dan. "So," she started between mouthfuls of grilled chicken, "He's getting married."

Nate's fork clattered to his plate in surprise, and he looked up at her to find her face set into an expression that he could only read as acceptance. "Yes," he spoke slowly, careful to avoid any potentially hidden traps in her statement, "He is."

"To Caroline Whitlock," she let out a low chuckle, thinking about the supermodel who made national headlines for suing her management firm.

Nate studied her, his blue eyes wide with concern, but he didn't bother responding. Chuck's relationship with the model wasn't a secret; they'd been photographed together dozens of times, and even Blair knew that they were serious.

"It's surreal," she said absently, cutting her chicken into tiny bites to occupy her hands, "I thought she was just a distraction - like Eva - someone for him to come home to, to keep his bed warm and present the picture of the reformed family man for cameras. I never thought…" She exhaled slowly, letting the words wash over the table. "When it wasn't us, I never thought it would be someone else."

"Blair -" Nate warned.

"No, I'm okay," she smiled, "Really I'm okay." She paused in irritation as the waiter refilled her wine glass, not wanting an audience for this conversation. "Tell me, though, is he happy, I mean, really happy?"

"Honestly, Blair," Nate answered cautiously, "I've never seen him happier."

"Then," she swallowed the painful lump forming in her throat, "I'm happy for him."

"Can we change the -"

"I want you to do one thing for me, Nate," Blair batted her eyes innocently, donning an expression that Nate couldn't resist, "Take me as your date to the wedding."

"What?" He pulled his hand back from hers, eyes widening, "Blair, that's crazy."

"I promise I don't have an ulterior motive here. It's closure for me, and, despite everything that happened between us, he's still one of my closest friends. I miss him…and I miss Serena." She wiped the corners of her mouth with her napkin. "Don't you miss the way things used to be?"

"Of course, I do," he sighed, "But, Blair, this is his wedding. I can't bring his ex!"

"Come on, Nate," she pouted. "It's easy. He'll be so busy with guests and festivities that he won't even notice I'm in attendance."

"No, Blair, I can't do that to him. He's in a good place, and I'm not going to risk messing that up for him. I'm sorry."

"How about this," she switched gears, "Arrange a get-together – a dinner, a party, I don't care, and invite Chuck, Caroline," It took everything in her not to grimace at the name of her ex's fiancé, "and Serena."

"Can I at least think about it?" He threw two one-hundred dollar bills on the table.

"Of course, but all you have to do is get us in the same room." She settled her purse in the crook of her elbow as Nate placed his arm around her shoulder to guide her out of the restaurant. "I know that things aren't going to magically go back to normal. I know that I messed everything up irrevocably, but I'll never be able to make it right if I never see them again. I miss my friends. I want them to be happy, but I need to be happy, too, Nate. I haven't been happy in so long."

When they reached the curb outside, he wrapped her tightly in his arms. He knew that she'd brought a lot of her misery on herself, but he hated to see her suffer. Over the years, he'd tried to find ways to at least mend the friendship between Blair and Serena, but the blonde was proving to be just as stubborn as the brunette standing in his arms. The one time he'd brought Blair up to Chuck, he'd ended up with a fist-sized hole in his wall, so he never tried again. As the years went on, he realized that Chuck had finally overcome many of the demons that haunted him for his entire life, and he couldn't let Blair derail that.

The hardest decision he'd ever made was lying to Blair about Bart's death two years earlier. He sent her to France on a fool's errand so that she couldn't interfere, and by the time she figured out what had happened, the funeral was over and Chuck was in California, away from the temptation of being pulled back into the darkness with Blair.

As she pulled away, he told her, "You deserve to be happy, Blair, and I'll do everything I can to help you get there."

The only problem was that no one knew what happiness looked like for Blair anymore.

A/N: I'm so overwhelmed with the positive response to the prologue; thank you all so much for the kind and thoughtful reviews. I know that I use the future fic/flashback structure in several of my fics, but it's honestly one of my favorite ways to set the tone for an angsty fic.