The Sweetest Irony

And oh, look at what's left of you and me;

Just passing ships with wreckage left from all our misery.

Chuck knew the moment he heard her voice that it was all too good to be true.

Throughout his vigil on the roof of the Empire State Building he'd told himself that he would wait—that he would wait long past 7 o'clock, just in case she was somehow delayed or she changed her mind at the last possible moment. But in the end, he'd exited the roof at precisely 7:01 PM, tossing the peonies in the trash, the wrapper destroyed by the way he'd clenched it in his fist as if it was a lifeline he wasn't ready to let go of.

Jenny's appearance had been fortuitous; a twisted, perverse luck derived from the parallel universe that seemed to haunt the Bass men. His fingers and his lips had been numb—in fact, all of him had felt dead. Hollow. Empty. Devoid of emotion completely. As if the idea that he could lose Blair Waldorf forever was too great of a pain to even contemplate.

So instead of contemplating, he'd forced himself to do the one thing that he'd believed was off-limits since that one night at the beginning of junior year. He'd even apologized to Jenny for it once—and he never apologized to anyone, for anything—though, in the end, he thought that taking her virginity after all negated the apology.

Still, he'd told himself as he lay in bed next to Jenny and steadfastly refused to consider the ruin of his life, he was still Chuck Bass. In fact, he'd done the one thing that could reassure him that he was still the man that he'd believed he was—dirty and devious and rotten to the core.

Blair's voice was a sweet, vicious irony; breaking into his thoughts, destroying his carefully planned downward spiral. It was his luck, Chuck could only sneer at himself, that she'd come only after he'd done the one last thing that she could never forgive him for.

"Excuse my confusion," he stuttered, nearly unable to speak because of the panic that Blair might notice Jenny in his bedroom. "I didn't expect to see you tonight… or ever again…" Or else he never would have gone to that darkest of places, would never have followed Jenny into her chamber of horrors.

"Sorry I was so late," she said. God, he wished that she hadn't been late, or that he'd been smarter and stayed. Trusted that she would show up-but he'd never really thought she would. He couldn't believe that he deserved her loyalty after what he'd done to her with his uncle.

And he especially didn't deserve it after what he'd just done with Jenny.

"I waited," he said, even though it was a lie. Even now he was a coward and couldn't tell her that he hadn't waited because he'd believed it was over.

"Dorota went in to labor, she had her baby. I wasn't going to show up, I was resolved not to, every bone tried to slow me, every voice in my head screamed don't . . ."

He understood that insistent inner voice; he'd been hearing it the moment he'd laid a finger on the girl in his room. He'd slept with girls after Blair -but that was only because he was Chuck Bass and that was what he did- but what he'd done with Jenny had been him burning that final bridge.

"But?" Chuck didn't want her to say it. If Blair said it, if she truly, honestly meant that they could be together, it would be even worse because when she found out about Jenny -and it was inevitable that she would- she would end it for good. This second chance was over before it had ever begun.

"...but I didn't listen, I followed my heart because I love you. I can't deny that our path has been complicated, but in the end love makes everything simple."

Except it wasn't simple-the one thing that Chuck had learned since falling in love with Blair Waldorf was that their love affair was a lot of things, but the last thing it could ever be was simple.

He'd played the relieved, attentive boyfriend, though Blair could never know his relief when he'd discovered Jenny missing from his bedroom, but the entire time, he'd known that it was too good to be true. There was too much wreckage, too much trying to pull them apart; everything that happened had pushed them to the breaking point, but Jenny would be the girl that broke Waldorf's will to see this through.

When she told him that the night had never happened, the expression in her eyes as cold as it had been during the betrayal of Serena, of Nathaniel, of her father, Chuck knew that he'd made damn sure there was no going back.

The Titanic was generally considered the greatest shipwreck of all time, but Chuck knew that their relationship—the voyage of the "We're Chuck and Blair; Blair and Chuck"—had not only been doomed from the start, but that unlike the Titanic, there weren't even debris left to search. There was nothing left—the memories erased from her mind the way she purged the unwanted food from her stomach.

In some delightfully, excruciatingly painful way, it was almost a relief; it was as if Chuck could finally admit to himself that there was no more need to try, because whatever he could do, it would never be enough to fill the void that had been left behind.

And then he'd been shot, the bullet tearing through skin and flesh and muscle, and he'd known for sure.

Her ship was still sailing; it was his that had crashed and then incinerated, falling to its final, inevitable resting place.

AN: Dialogue was taken from episode 3x22, "Last Tango, Then Paris."