After an admission like that, Castiel found himself unable to say anything and had a hard time hiding the stupid little grin that crossed his face as Sam downed his first whiskey shot. "Anyway, what happened after that?"

For a split second, Castiel felt his heart sink because he thought the next thing would be that before he realized that it was something else first. "Dean did some research as to who I am and confronted me about my connection to the Novak gang. It was his version of payback for my surprising him."

"So, you're part of the Novak gang, huh?"

Castiel spun on his heel to catch the man, his hand automatically going for his handgun. His fingers curled around the familiar grip as his eyes landed on a man he never thought to see again. "I should've known that you would discover more information on me, Mister Winchester."

Dean's features were set, his face a perfectly blank mask. Castiel watched his eyes attempt to land on a single emotion. Unfortunately, they decided on disappointment, but not before the brunette saw something he could've sworn was curiosity. "You know how the old saying goes. 'Curiosity killed the cat'. Thought, I guess that applies to my line of work in general. You already knew that thought." The blonde observed Castiel for a moment. "I never figured I'd live long enough to meet a member of the Novak family."

His features were schooled except for the tiniest narrowing of his eyes for a second. "It would be highly presumptuous of you if you think I'm a relative of the Novaks." Castiel cocked his head to the side slightly. "What makes you think I'm a Novak?"

The P.I. grinned a little. "I'm a high profile target in the Novak's books. They wouldn't just send anyone to kill me, not if I know them, and I do."

Castiel was quiet for a few long moments. "Why do you believe that?"

"I've got my sources."

The brunette's eyes flicked over Dean's face, searching for answers. "Gabriel," he finally said. "He's the only one I know of who would be willing to cooperate with you besides Anna or Balthazar."

Dean stared at Castiel, less amiable then he had been when they met last. "What makes you think any of them would cooperate with me, especially since I'm a well known enemy of the Novaks?"

"You're giving yourself too much credit for one. Another could be that while they act as if they do not care, they are just as human as anyone else." Castiel narrowed his eyes again when Dean let out a little "Huh". The brunette felt his body tense in preparation for a fight. "What?"

The blonde shook his head slightly. "I'm just trying to decide if you're putting yourself in that group or not. Either that or you're just really close to those three members."

"So Dean sought you out," Sam summarized as Castiel downed a shot of whiskey.

The bartender nodded, his throat burning slightly. "Hunted down would be the more accurate term. Apparently he found all of the information he could about the Novak gang, including where their most common meeting places were."

Sam nodded. "But Dean was right. You are a part of the Novak family."'

Castiel sighed and nodded. "My eldest brother was the leader at that point in time. I have no idea if he still is. The other three I mentioned - Anna, Balthazar and Gabriel - are also relatives of mine. Gabriel is my older brother. Anna and Balthazar are my cousins. Unfortunately, they also suffered from my cooperation with your brother."

"Why? I mean, no offence, but you're the one who worked with Dean, not them. They shouldn't of been punished or whatever happened." Sam paused, taking a second to look at Castiel's expression. "Your brother found out."

Castiel nodded again. "Before I was punished for my cooperation with Dean, he told me that they were foolish in assisting me in my cooperation because they would be punished as well. I have not seen any of them since and believe them to be dead on his orders."

Sam was silent for a moment. "Could they have actually helped him without you knowing it?"

The bartender shrugged. "It's possible although unlikely."

A series of knocks against the bar doors startled them out of their conversation. Cautiously, Sam opened the door after unlocking it with the key Castiel had left on the bar. "Dean."

His older brother half-smiled. "Hey, Sammy. Can I come in?" Sam nodded after glancing back at Castiel to get the bartender's approval. Dean took a deep breath in before walking into the bar. "Hey, Cas."

Castiel nodded curtly to the P.I. "Dean."

Sam quickly closed and locked the door before returning to his seat at the bar. "We were just wondering about something Castiel said."

Dean looked at the dark brunette, surprised. Castiel nodded again. "It was when you confirmed with me that I was a Novak."

"So this is about whether I ever met Gabriel, Anna or Balthazar, right?" Sam didn't look surprised, but Castiel did. The P.I. grinned at the bartender. "You thought I forgot about it? Shame on you, Cas." Dean nodded, sitting at the bar beside Sam, across from Castiel. "I actually did meet them because they got curious."

"Well, Cassie wasn't lying when he told me you would be prepared to shoot me if you ever met me."

Dean watched the man step out of the shadows, tossing a piece of candy into his mouth. "And who the hell are you that he would be so certain I'd shoot?"

The man scoffed, a grin spreading across his face. "I go by The Trickster on the streets. Cassie knows me by my real name though, since we are related. Name's Gabriel Milton." He waved a hand at Dean, practically ignoring the gun pointed at him. "Put that thing away. It's not like I'm gonna attack you or something." Hesitantly, the P.I. holstered his sidearm. "Alright, now we can talk." Gabriel sat down behind Dean's desk, sticking his feet up on the sturdy wood.

"What the hell does The Trickster want with me?"

Gabriel grinned, tilting his head to the side. "You are adorable. Now I see why Cassie couldn't resist talking about you. Speaking of Cassie, I'm surprised you know who I'm even talking about." Dean rolled his eyes, resisting the urge to either pull out his gun and shoot Gabriel or punch him. "It's not like anyone else calls Castiel by a nickname."

The blonde paused for a moment. "I call him Cas in my head."

He felt himself being scrutinized when Gabriel looked up at him again. "Well, I'll be damned. A P.I. who actually cares about the cases he works." After a second, Gabriel was off again. "Anyway, that's not what I came by to talk about, Dean-o. I was kinda wondering how the hell you and Cassie got to be all buddy-buddy out of the blue."

Dean cleared his throat. "I was being shot at, Cas had a conscience."

Gabriel narrowed his eyes for a second. "Cassie wasn't even supposed to be there. I'd taken him out drinking and got distracted. I assumed he'd gotten home on his own."

"Whoa, whoa, whoa, stop there, Dean." Sam held his hands up, a grin on his face. "Castiel was out drinking with his cousin?"

Dean shrugged. "I never did get confirmation on whether what Gabriel had been telling me was true or not." He looked over at Castiel, who was now sitting across from him as they'd moved to one of the tables in the bar. "Was Gabriel right?"

Castiel didn't meet Dean's eyes. "Please continue explaining what happened."

"Anyway," Gabriel continued. "I'm here to make sure that you don't go do something stupid like break his heart or anything."

The blonde rolled his eyes. "It's not like I've asked him out or anything."

Gabriel let a huge shit-eating grin cross his face. "Oh, I wouldn't say that. But, you did track him down and confront him about being a Novak, especially Michael's little brother." He nodded. "Yeah, that's not something a couple does at all. Confrontations and the whole drama? That's a regular mystery, not a cheesy romance novel." Dean rolled his eyes again. Gabriel tilted his head, this time curious. "Huh. You really don't get it." He stood stretching. "Was nice talking to you, Winchester, but I gotta get going. See ya around."

Dean watched Gabriel saunter nonchalantly out of his office. "That was the weirdest thing that's happened to me all day."

A/N: I'm close enough to New Years to say Happy New Years again. HAPPY NEW YEARS ALL! I'm happy I actually had the majority of this one down earlier otherwise it might've been a really long time before I updated again. Anywho, did you all like it? Even the random Gabe? I'll get to Balthazar and Anna later...ish. Honestly I have no clue whether I'm writing them correctly or not so I'm just sitting here with my fingers crossed. Reviews and feedback are loved!

UPDATE 8/7/14: "Whiskey and the Novak Gang" chapter title changed to "Whiskey and A Gun" by Maggie Rose.