Chuck Bass has always prided himself on living without regrets. They serve no purpose, they change nothing, and the constant litany of 'could of, would of, should of' is enough to drive one mad. Still, in his seventeen years, he has grudgingly acquired a few, and the majority of them concern her.

He regrets hesitating on the dance floor before chasing after her on the eve of her cotillion. He regrets insinuating she was a slut by comparing her to a well ridden horse. He regrets standing her up on a helipad. He regrets every day of the summer in which he did not follow her to Tuscany and beg her forgiveness. He regrets being too proud to admit he loved her before she'd left the White Party with another man. He regrets not agreeing to say 'I love you' at the same time as her on a rooftop in Brooklyn. He regrets throwing her 'I love you' confession back in her face after his father's funeral. He regrets leaving the comfort of her embrace later that same night and fleeing to Thailand. He regrets cancelling their dinner together so he could get drunk and high with Jack and some prostitutes. He regrets taking his anger and embarrassment at being set up by his uncle out on her by accusing her of trying to play wife. He regrets trying to forget her with a manipulative whore who'd taken advantage of his desire to be the hero for once and conned him out of thousands while Carter Baizen conned himself into Blair's bed. And lately… lately he's regretting not fucking her when she'd asked at the Vanderbilt reunion.

He would have regretted that too, of course. But perhaps not as much as he regrets turning her down seeing at that decision had propelled her back into Nathaniel's arms. If he had given in, had just taken her as ordered, he might've hated himself, but he wouldn't have lost her completely. Sleeping with her at that party wouldn't have helped matters, wouldn't have fixed her or stopped her downward spiral, but surely that was something he could have dealt with afterwards, when she wasn't drunk and desperate and hell bent on social suicide.

But instead, he had left, had tried to do the right thing, only to discover when he'd gone to her penthouse later that evening that the right thing had in fact been the wrong thing.

It's ironic that when he was the gentleman who refused to take advantage of her vulnerable emotional state, Nate was the bastard who had.

And Chuck can't even really blame his friend. It was his own fault more than Nathaniel's. He should never have let her spin so far out of control in the first place. He should have been there for her, should have fought for her long before Serena had prompted him to.

But the thing was he hadn't known how. He had never had to fight for anything in his life. Being a Bass, he's grown up believing that everything had a price, and with the right amount of money, anything worth having could be bought. It had taken her, a slip of a girl with chestnut curls and cupids bow lips and dark, flashing eyes to teach him otherwise, to show him that love given freely is beyond value, and also painfully easy to take for granted.

Unfortunately, it was a lesson he'd learned too late.

Nate won. He lost. Game over.

So what did it matter that he'd been about to man up and tell her the truth about his feelings when he had shown up at the Waldorf residence in the dead of night, that he'd been ready to throw caution to the wind and confess it all? He'd missed his opportunity because he was a fucking coward.

He'd been terrified of the commitment inherent in those three words, because they were a commitment. To him at least. Once said, they could not be unsaid. There were no take-backs. Those eight letters were forever, which was why Chuck could acknowledge his feelings for her so effortlessly to Nathaniel, to Serena, to anyone who would listen, but choked up whenever he tried to say them to her, the person they were meant for.

But that hadn't been what had kept them from being together. It had never actually been about saying or not saying 'I love you.' Not really. It was his own insecurities that had kept them apart, his fear that she'd see through all his careful posturing to the boy inside. That she'd be disappointed like his father. That she'd disappear like every other woman in his life. Like his mother when he'd been born. Like his nannies when they made one too many passes at his dad. Like Bart's ever changing girlfriends when they got too clingy. Like Serena when she'd fled to boarding school and left him behind to clean up her mess and mediate the increasing awkwardness between Nate and Blair, making him the constant third wheel in their relationship. Like Lily when she'd been about to abandon both father and son for an old flame in Brooklyn the night of Bart's fatal accident.

He might not have had the greatest track record with the opposite sex, didn't have many examples of their loyalty, but regardless he had reached a place where he'd been willing to take the risk. For her.

"Fight for her," Serena had told him. "Make her feel safe." And there had been a third command from his sister too, one that had blazed in her eyes, unspoken but obvious. Tell her you love her.

And he had planned to, had planned to give her his heart and soul, his darkest thoughts, the worst things he's ever done, his hopes and dreams and fears and doubts, everything that made him Chuck Bass, all of it laid bare for her so she'd know she wasn't the only one who felt lost. He felt that way too. Lost without her, without his father, without a smirk on his face and a scotch in his hand and a nameless bimbo on each arm and the whole world not giving a shit because he was Chuck Bass, heir to Bass Industries, before he became Chuck Bass, colossal fuck-up who'd lost the one thing his father had entrusted him with. He didn't know who he was anymore either, but he had wanted to find out. Find out with her because on the second worst day of his life, the day they'd put his father in the ground in a New York cemetery and the reality that Bart wasn't ever coming back had slammed into him, without even thinking about it, he'd gone to her and she'd taken him into her arms and he'd found enough solace there to sleep, because she'd made him feel safe, and Goddamn it he would do that for her, would be the man she needed him to be, a man his father would have been proud to call his son.

So he had gone to her. No flowers that time to throw at his feet. No pretty speeches about not giving up in the face of true love. No games or seduce and destroy missions to hide behind. No, for once it had just been him, Chuck Bass, everything he was, everything he would ever be, and a private prayer that it would be enough, only to find out that it wasn't. Because someone else had beaten him to her, leaving an all too familiar jacket in her foyer.

His first instinct had been to rush up the stairs and break Nathaniel's face. But he had ended up setting the coat back down where he'd found it, returning to his room alone, and drinking himself into oblivion. And the next morning when Serena had inquired how it had gone with Blair, he had glared at her in stony silence, his pallid complexion and bloodshot eyes more than answer enough.

The girl who had once claimed to stand by him through anything now stood by his best friend, the Upper East Side's own golden couple together again, and the subject of Chuck and Blair, Blair and Chuck was closed forever. She was living her fairytale, and he was… he was intoxicated more often than not, and his life was slowly reverting back to how it had been before…

You were amazing up there.

…before a champagne fueled striptease that didn't mean much in the grand scheme of things.

Or at least that was what was supposed to be happening, and would be happening if reminders stopped imposing themselves upon him.

Like now for instance.

"Nathaniel," Chuck greets as he opens the door, trying to summon enthusiasm into his voice and not having much success. "To what do I owe the pleasure?"

"Don't act surprised," Nate admonishes as he steps past Chuck into the van der Woodsen penthouse. "I've been trying to get a hold of you for a few days, as I'm sure you are well aware."

"Yeah… about that," Chuck drawls uncomfortably. "I've been busy lately." It's a rather lame excuse, and he is certain Nate knows that, but it's the only one he has that sounds reasonably true, and is even a little accurate.

It isn't that he has been avoiding Nathaniel. It's just that the sight of Nate with Blair turns his stomach, even more so than it had the first time. It also makes his heart clench, makes it hard for him to breathe, makes him want to get on a plane and disappear to some foreign city and never set foot in Manhattan again. But as much as he wants to, he can't do that. Bass Industries is here, and Lily had used a loophole to wrest it away from Jack, and when he turns eighteen in a few months time, she expects him to show the board that what they had walked in on had been a fluke and that he was more than capable of taking over his father's legacy as CEO.

So between ignoring Nate's calls and draining bottles of scotch and banging vapid brunettes, he's been pouring over company memos, profit margins, inventory reports, investment portfolios, personnel files, attempting to understand how Bart did it, how he took a small business and made it into a global franchise, wishing he had…

Blair.

…someone there to help explain it to him so it wasn't so blasted overwhelming.

And if that doesn't leave him feeling particularly social, so much the better. The less he goes out, the less likely he was to run into them, except that strategy has apparently been thwarted because they keep coming to see him. So far it has been separately, but soon they'll probably come together, holding hands and smiling at each other and kissing and looking so goddamned picturesque he'll have to swallow down vomit.

What fun.

"I've wanted to talk to you," Nate says into the tense silence that had descended.

Already dreading what invariably comes next, Chuck moves towards the wet bar to mix himself a drink. It's scarcely noon, but he is so not drunk enough for this conversation. "Oh yeah? About what?" he mutters, feigning ignorance to buy himself a few more precious seconds before the reason behind this visit is spoken out loud and he can no longer pretend that it isn't all about her.

"Come on Chuck," Nate sighs. "You know what I want to discuss."

"Actually, Archibald, I haven't the foggiest," Chuck sneers with a touch more vehemence than he intends. "So why don't you stop pussyfooting around whatever it is you came here for and just spit it out?"

"Fine," Nathaniel growls, a bit of his own temper rising. "I know Blair came over the other day and I want to know if you two got your issues worked out."

"Why don't you just ask her?" Chuck deflects, deliberately stalling.

"I did ask her," Nate replies swiftly. "And now I'm asking you. Did you get your stuff worked out?"

Chuck glances away from Nathaniel's inquisitive expression, the amber liquid in his glass suddenly quite fascinating. "There was nothing to work out," he shrugs. "She made her choice, and I moved on."

"So it's over between you then?"

"Whatever was between Blair and I was over a long time ago, Nathaniel," Chuck insists, hoping his friend will let the subject drop and leave well enough alone. "There's nothing between us anymore," he adds, a hint of bitterness seeping into his tone.

Nate's gaze narrows. "Blair said that too."

"She did?"

"Yeah," Nate confirms.

"Then why double check with me?" Chuck scowls. "Do you not trust her?"

Nathaniel bristles at the accusation, standing up straighter. "Of course I trust her."

"Then what is it?" Chuck snarls softly, cocking one brow. "Do you not trust me?"

"No, I trust you," Nate sputters with a dismissive gesture. "It's just…"

"Just what, Nathaniel?" Chuck retorts, his jaw clenching.

Nate takes a deep breath as if steeling himself for a battle. Then he asks the one question Chuck is not prepared for him to ask. "Do you love her?"

The inquiry hits him like a kick to the gut. "What?"

"Do you still love her?" Nathaniel repeats, staring at him intently, waiting for a response.

After several long moments, when it becomes clear that Nate is not going to back down without an answer, Chuck turns away, gulping at his scotch. "…no," he whispers eventually, the denial barely audible as he concentrates on the burn of the alcohol in his empty stomach.

Nathaniel grabs his shoulder, whirling him around. "Look at me and say it," he orders.

"Excuse me?" Chuck snorts as though the very idea is preposterous.

But Nate is not to be deterred. "Look in my eyes and tell me you don't love her," he grinds out, tightening his grip on Chuck's arm so he can't move away again. The golden boy's words both a challenge and a command.

"I…" Chuck stammers. "I… This is ridiculous."

"You can't do it," Nathaniel announces, letting his hold on Chuck loosen enough that the dark haired boy is able to wrench free. "You do still love her."

"What does it matter if I do or not?" Chuck snaps harshly. "She chose you, remember? End of discussion." With that, he picks up the crystal decanter Lily liked transferring the scotch into, and pours himself another highball.

"But if you – "

"I don't!" Chuck hisses, cutting Nate off abruptly. "I don't love her, okay? Now can we drop this?"

"Fine," Nate declares angrily. "So things are over between you and Blair. Perfect. What about us? Are we over too?"

Despite his quiet fury, the corner of Chuck's mouth twitches. It's just too good an opening. "I didn't know we were dating Nathaniel," he smirks.

"I'm serious, Chuck," Nate deadpans, expression grave. "Are we still friends?"

I care about three things, Nathaniel. Money, the pleasures money brings me, and you.

"Yeah," Chuck nods, a ghost of a smile on his lips. "We're still friends."

"And everything's fine with us?"

"Yes. Everything's fine."

Nathaniel inclines his head, indicating the tumbler in Chuck's hand. "Then why have you been squeezing that so hard your knuckles are white?"

"I – "

"You've been doing it since you picked it up," Nate explains. "Right after I got here. Why is that?" Blue eyes search brown for a second, then he continues, "Are you not okay with me being together with Blair again?"

Chuck swallows, forces himself not to look away, to betray nothing. "I… I just want her to be happy Nathaniel. And if that's…"

You don't belong with Nate. Never have. Never will.

"…if that's with you, then yes. I'm okay with it."

And while it isn't a lie, it isn't the whole truth either.