He dropped Cas off at the motel, not bothering to stop and check in with Sam. He'd just successfully finished a job, and that meant he deserved a drink.
That being said, everything he did meant he deserved a drink, these days.
Leaving the car in the lot, he walked onto the high street, checking out each shop as he went along. It was coming up to five in the afternoon, which meant that, for once, he was going to start drinking at a socially acceptable time. Not that it mattered – it was always five somewhere.
After a few minutes of walking, he found himself at a bar... unsurprising, really; every town has at least one in some form or another, and nowadays Dean was as good a hunter in alcohol as he was in the supernatural.
The bar was much more peaceably named than the last for Dean's liking; 'Tony's'. A nice, non descript name, nothing to remind him of anything. Tony, average Joe, the local watering hole for the masses. Plenty of room to lose himself in a crowd for an evening.
The bar was fairly quiet, it being only just five in the afternoon, but he guessed it would get busier as the night went on. Friday's were busy for bars.
Though, as he looked at it as he went it, he decided that might not be the case.
It fell into one of his two favourite categories of bars. The first were the 'chick bars', often used for hen-nights or where women met up with their friends. These bars usually sold plenty of cocktails, and were generally female friendly. These were the bars Dean would go to when he wanted some company for the night.
This bar fell into the second category. The lighting was pretty dull. A thin layer of grime covered the surfaces. Seating was sparse, but few were occupied. He was unlikely to be bothered, which suited him fine. Recently he'd had more of a preference for this type of hole, though he would, of course, return to category 1 when he desired its services.
He sat down on one of the stools, placed his elbows on the counter and got settled. The bartender turned to him, not saying anything, just raised an eyebrow expectantly.
"Not the talkative type?" Dean smirked. "Suits me just fine."
"I'm plenty talkative if you're tipping well enough." The man grunted.
"Yeah, well; I think I can make do without that." Dean said. "Gimme a whiskey."
The man silently obliged, passing Dean a glass with a shot. He drank it in one.
"Keep 'em coming." He grunted.
Dean had only been there about an hour and a half. By this time he was slumped on the bar, various whiskey glasses and beer bottles around him. He was playing with the one immediately in front of him, peeling slightly at the paper label. He then put the bottle to his lips, taking a sip.
A damn fine way to spend an evening, Dean surmised. It was artistic, poignant, yadda yadda; people drank alone in bars. The best type of people.
The bar hadn't got any busier. Some had come in and out. No-one really stayed that long, no-one really talked – they were there to be alone, and they respected that of each other.
So Dean didn't look around when the door opened again. Why should he? It wouldn't be anything to do with him.
He didn't even look up when someone sat down next to him. Sure, it was an odd choice, there were four other stools to choose from, two of which weren't right next to him. That was bad bathroom etiquette. But he didn't bother looking up.
"Not gonna say hello, Dean?"
A woman's voice greeted him, and he blearily looked up. He groaned and automatically reached behind him, grabbing for his gun. She grabbed his arm, her sober strength a little overpowering against his swaying drunkness.
"No guns, darling."
"Olivia." Dean said gruffly, trying to focus on at least one of her. "Not hiding in the back room, this time?"
She looked to the bartender. She frowned slightly, taking in the thick moustache on his upper lip, his weathered skin. "He's not my type. Besides, you got here first this time."
"Still; why aren't you hiding?"
"Me hiding?" She laughed. "You're the one who moved towns."
"Seemed responsible." Dean slurred, taking another sip of the beer. "Sammie's decision. I'm all up for ganking you."
"'Ganking' me?" She winked. "Sounds kinky. Nah; didn't Cassie tell you about our little chat earlier?"
"He did." Dean nodded, brushing past her innuendo. "That meant to change my opinion?"
"Up to you, love." She sighed as she waved to the bartender. "Vodka, please." She smiled.
"You're trying to torture him." Dean stated.
"Him?" Olivia blinked. "I only ordered a drink! Hardly a difficult order."
Dean glared at her.
"Oh, Cassie? Yeah, a bit. Does that matter?"
"I doesn't really make me like you, no."
"Why do you care? You hate the guy." She shrugged, looking at the hunter. She paused when she saw his face, though, and broke into a wide, triumphant smile. "Oh! You're beginning to get the warm fuzzies all over again! Mozeltov!"
"There are no warm fuzzies." Dean corrected her. "But you are trying to screw with a guys mind, and I'm not good with that."
"Oh, it's not like you've not handed out a few threats in your time." She scoffed, taking the drink in front of her. "Thank you, dear. We both know that, if you were in my shoes, you'd be out there, guns blazing."
"You're playing games." He pointed at her with his bottle before taking another sip.
"And you don't?" She laughed. "When it was lovely old Yellow Eyes, you weren't going to hold any tricks. You did everything, and you killed him."
Dean sighed. "Olivia..."
"Please," She stopped him. "Livvie."
"No-one but your boyfriend calls me that. I can't be bothered to correct the idiot."
Dean glared again. "Livvie... That was a completely different situation."
"Do enlighten me."
"Yellow eyes was a demon, who's big bad mission plan was to turn my brother into the spawn of Satan."
"Oh, yeah? And how'd that work out for you?"
Dean's hand moved noticeably towards his gun again, but she stopped him.
"Sorry, uncalled for. I've got no beef with you." She tipped her drink to him before taking another sip. "But come on. Cassie killed my Dad-"
"-Which sucked." Dean chimed in.
"Indeed. And I can't just let that go."
"You're going to laugh at me if I tell you he's a changed man, aren't you?"
"I dunno. Try me." She looked at him with all seriousness. "Then he body jumps me, and I get to see my Dad getting killed. I get the memory pumped through me. I get the back story, context, the guy's bloody mental state while he does it, and you know what?" She took a drink, finishing it, and gesturing for another. "I still want him dead."
"Not just dead, you want him to suffer."
"That too. Completely understandable, if I do say so myself." She smirked.
"And you see why I have to stop you." Dean took a sip.
"Naturally. The aforementioned warm fuzzies."
"Not freaking warm fuzzies!" He cried.
"I don't know!" He slammed down his drink, spilling it across the counter. "All I know is that for some crazed reason, I have to look after the damned idiot. It's my job. It's always my job."
"Diddums." She cooed.
"Bite me." He growled.
"Is that an invitation." She asked softly, turning in her chair to look at him, tilting her head coyly and looking at his neck. She gnashed her teeth.
Dean looked taken aback, clearly confused at her motives. "Last time I checked, it's your enemy's enemy you get friendly with, not your own."
"Oh, we're enemies now?" She giggled. "How exciting."
"Well, I figure at some point, I'm going to have to stop you."
"Oh, that's not just yet." She sidled closer. "We've got time."
Dean knew it wasn't a great idea to flirt with her. Not at all. But the alcohol fuelled haze was putting a definite dampener on his better judgement.
"How much time?" He asked, leaning in.
"Oh, that would be telling." She smiled. "Wouldn't want to ruin the surprise for your boyfriend, now, would I?"
He growled. "I am not gay." He told her, a second before his drunken lips met hers.