A/N: First Crossover. First VD. Be nice & try not to hate too much if Damon is way OOC. ;) Takes place after Damon kisses "Elena" in the finale…let's just pretend he can move super fast all the way to New York. Lol. Oh, & early S4 for Gossip Girl. *nods*

*I own nothing, neither Vampire Diaries nor Gossip Girl. It is sad. *pout*

…

He hadn't been to New York for awhile, definitely not for the last few months. He'd spent that time back in Mystic Falls, making a strange transition from careless to caring, though in the most discreet way possible. Regardless, his caring ways had gotten the best of him and he'd made a turn for the worst. Stefan no doubt would be pleased he'd skipped down, but Damon knew it wouldn't be for long. He would have to confront his brother for kissing his girlfriend after he'd sworn he wouldn't repeat history. Though, technically he hadn't agreed to anything. That would be the easiest way out of a beat-down, he decided. Maybe if he made Elena hate him it would be even better.

It was pitch black in New York, the middle of the night just like where he'd come from. But unlike Mystic Falls, Manhattan was still brimming with noise and excitement, the lights practically blaring in his face. He wondered very intensely for about half a second if it was possible to be burned by just the lights if he was not wearing his ring. Soon enough though, he'd found a quieter, less bright section of the city, some streets into the darkness, and an shiny bar presented itself. He straightened his jacket and headed across the road. He didn't look to see if cars were coming, and he walked quite casually too. An ounce of guilt flooded through him when he heard vehicles screech in the middle of the street to keep from hitting him, but the smirk still remained in place on his face.

The place was crowded but he managed to find a few vacant stools available up at the bar. He sighed in what was almost exhaustion and headed for the nearest one. He paid no attention to the guy sitting next to him, who looked like the scotch in his glass was the most interesting thing he'd seen. He wondered if he was rich.

"Do you know…" the man began and Damon sighed, this time from irritation. He should have known someone would talk to him, but he had not been counting on a drunk rich kid in one of the less shiny bars of Manhattan.

"How many bubbles there are in a scotch glass?" he asked a bit sarcastically, his expression completely serious. "No, I haven't the slightest clue. But I bet if you ask that bartender" he pointed in the direction of the big-breasted brunette flirting with customers on the far end of the bar, "she'd be happy to inform you…of a great many things." He looked the boy over and waved his fingers around to get the attention of the male bartender closer to them.

The "drunk, rich kid" gave him a once over. "I'm Chuck Bass," he said, emphasizing his name slowly. It occurred to Damon that that answer was supposed to give him the key to everything he wanted in the world. He stared at him blankly and then smiled briefly at the bartender for delivering his drink. He took a swig.

"Is that supposed to mean something to me?"

Chuck blinked, confused at the reaction. "It's not just a name known in New York," he nearly stuttered. Damon smiled silently. He turned his head to face him.

"Really?"

"The Bass name is known worldwide. I happen to be the heir of one of the richest billionaires on the planet."

Damon turned his body fully to him and made a halfhearted effort to be polite. "And where is Daddy right now? Off screwing his secretary or your mother's psychiatrist?" He took a sip of his drink, waiting for the answer. He was not rattled at all when Chuck's eyes darkened and his hands tightened on his glass of scotch.

"No."

Damon tilted his head to the side. "Mmm…are you sure?"

"He's dead," Chuck said, before Damon could continue his taunt. Damon's face paled and a thick guilt settled in his stomach. He wanted to apologize but knew the words were not in him. He couldn't remember the last time he'd apologized. His mind had been spinning with Elena all night. It was all he could think about when he was stuck on the floor amongst the flames in the basement of that old building. It frightened him that neither Stefan nor Katherine were immediately on his mind.

"But I'm sure you know nothing about that," he spat, drinking down the rest of his scotch and signaling the bartender for more. He waved a way the girl's attempt at getting him some.

Damon decided not to get into a heart-to-heart. It was only recently that he'd developed that capability with Stefan and Elena. No one else got that privilege, not really. Only when he was in need of any other's assistance, and then only the very necessities were offered up.

He smirked. "No lay tonight, huh? She looks easy," he encouraged him, continuing his teasing along the way.

"I have a girlfriend," he said nonchalantly. If Damon hadn't imagined it – which he was sure he hadn't – the boy almost seemed regretful.

"An unwilling participant in the relationship, I take it?" He pushed the glass once filled with liquor to the side, signaling for the bartender not to interrupt for the moment. One look and flickering of his pupils did the trick.

"No, no, it's not that, it's just…" Chuck sighed. "Exhausting."

Damon laughed. "Well, you certainly sound like an unwilling participant. What is it? Is she rich—" He stopped himself at the ridiculous possibility and laughed. "No, of course not. You're rich. I forgot."

Chuck reached for his glass again.

"She foreign?"

The glass halted halfway to his lips.

"Ah." He sounded pleased. Chuck looked at him.

"You don't know the situation. Probably best if you just order another drink." He drank some more of his drink. Damon whistled and started to slide off his seat.

"Okay, probably best if I leave you alone to your brooding too." He laid some money on the smooth surface of the bar counter and made to leave.

"Know nothing of love either," Chuck mumbled into his glass. That froze Damon straight to his spot. He turned and looked at him, still drinking. He pulled the glass out of his hand with a quick movement, ignoring the glare he had quite expected but hadn't cared to acknowledge from Chuck Bass.

"This girl that you're not over…"

Chuck's eyes narrowed a little, probably trying not to give away the fact that he had not expected Damon to know. He said nothing, waiting for the perfect comeback to come into his mind, even while he was drunk.

"I'm guessing you haven't killed anyone she's loved, so—"

"What?" Chuck asked, clearly having not expected what Damon had just suggested.

"Well, has someone tried to kill you?" He offered up the other option. Chuck was clearly hesitant but eventually nodded.

"Yes," he said quietly.

Damon relaxed into his chair and tried very hard to clear his mind of Elena, of when she'd saved him. It was not easy. He didn't know how to continue. For some reason he felt a strange bond forming between him and this Chuck. He knew he'd be gone in the morning and they'd never see each other again, but somehow he still felt the need to stay near him. They had common ground, he believed, on some level. The next thing the boy said confirmed those lingering, heavy thoughts.

"What about the girl you're not over?" he asked, silently confirming that Damon had been right in his assumption. "Have you tried to get over her? Be something you're not?"

"That would be my brother," he chuckled.

"You have a brother?" He sounded genuinely intrigued. Damon nodded once.

"Stefan."

"And this girl you're not over?"

"Anonymous." He smiled a devilish smirk. It was mirrored on Chuck's face. Chuck raised his hand to the bartender without even turning away.

"More," he said, his smirk not slipping for a second, even turning into a smile. "My friend here's gone on empty."

…

A/N: Soooo…..thoughts? Oh, and Chuck finding his relationship with Eva exhausting is not because of her, but because he's sort of living this 'double life' of trying to be himself with those who know him and yet someone he's not with her, so that she'll be with him because he looks good, moral, etc.