~~Four Months Earlier~~

Dean sighed. He had past "drunk" three shots of whiskey ago. He defiantly hadn't expected on getting wasted. Hell, he hadn't even planned on drinking tonight at all. But he had and what was done, was done. Him and Sam had stopped by this particular bar on their way back from Bobby's, whom they had helped with a nasty spirit problem while they checked un. They had been sent that way on a hunch of Bobby's anyway. Seemed like the people of Madison, Wisconsin were having themselves a demon issue and Bobby figured that the boys could handle it themselves. And right then, Dean was left in a an empty bar, waiting on the youngest of the Harvelle women to serve him up another shot of Jack.

Sam had carried his sorry ass to bed at least two hours ago, not as if they were counting. He had left the bar to head to the hotel, Impala in tow, so he could get "rest up." They had checked into the hotel Jo was staying at, mostly due to the fact that it was the closest hotel nearest the bar, which was a blessing in disguise to Dean, and Jo, both.

"That's it," Jo's voice chimed through the silence. "This is the last one and I'm cutting you off."

She slid a filled glass of whiskey forward with a finger, a hint of competition flaring in her eyes.

Jo had been drinking with Dean since the last of the customers had trickled out and her boss had given her the a-okay to lock up.

"Oh, come on," he countered, taking the glass in a hand. "You said that, what? Half an hour ago? And you even took shots with me after that."

"No way, Winchester. I'm a lightweight and even I'm holding my liquor better than you," she said, making her way from the behind the bar with her own glass. A smirk was tugging at the corners of her lips, fully aware of Dean's eyes on her.

"Alright," she said, clinking her glass against his as he took his shot to the air. "Bottoms up!"

They both slung their glasses upwards, their heads backwards, letting the amber liquid slide down their throats. Dean slammed his glass to the bar's counter top with a satisfied sigh. Jo gave him a look and chuckled. She took his glass and moved toward the sink behind the bar.

"So," Dean said, almost nonchalantly as he checked out Jo's ass. "I take it this is where you tell me to get the hell out before you get the bat?"

He was half-way expecting Jo to bring out a bat; that is, he was expecting it. But it wasn't as if he was if was truly expected it, after all she had stayed with him at least an hour after closing; he was just amused that that tight little ass of hers was already closing in on drunk, if not already, only 6 shots in. Jo laughed as she rinsed out the glasses and placed then onto the counter to dry.

"No, actually," she said. "But I do want you to get out so I can go get some shut eye. So, either way, you gotta get the hell out."

She moved, swayingly, to the back of the bar and towards the office. Jo grabbed the extra set of keys her boss, Keith, had left her. She had been working in Duluth long enough to be trusted by her employer, and was both grateful and thankful for that. Ever since she had left The Roadhouse, and before it's inevitable annihilation, she'd been feeling a little lonesome, homesick even (but the fact that she has started feeling welcome and that she'd had a few visits from her mom since the whole "Sam-almost-ripped-my-throat-out-through-my-chest" incident and was finally getting comfortable in this town).

JO walked out of the office with the bar's keys jingling as she did and propped a hand on her hip. She was the smirk plastered across Dean's face and raised a brow as her eyes met his.

"What," she asked.

As if snapping out of some idiotic stupor, Dean replied with, "Nothin'."

His grin didn't fade as he stood.

"But I guess if you're goin' to be that way, then I guess I'll head out to the motel and be outta' your hair."

Snorting, Jo lifted her hand from her hop. She slid past Dean and moved towards the door, saying, "We're going to the same place, idiot."

Dean blinked. How the fact that Jo was still staying in a motel room slipped his mind, he didn't know. He made his way out of the door while Jo locked up. The night's sky was clear, different from the past few nights when it was so cloudy that Jo had to use a flashlight just to make it back to her room. She waited for a stumbling Dean to catch up to as she moved towards the motel.

"Easy there, Tiger. Don't want to fuck with the merchandise."

With a wink, Jo contained up the streets. She was drunk, it was sort of obvious, but wasn't so drunk that she was falling all over herself. Dean, on the other hand, was pretty drunk. He'd been drinking ever since him and Sam had walked in and she had offered them a beer and a hug. Sam wasn't in the drinking mood tonight, quiet the opposite Dean was. Sam had only had a couple of beers the two hours he was there before scurrying off to bed.

Dean trailed behind Jo and it took her best effort not to bust out laughing. He was obviously trying to keep up with her, but even with his best effort, he was tripping all over himself; every now and then, a grunt from hitting the brick wall lining their way would emanate from behind her, forcing her to bite her tongue to keep from embarrassing him.

When they reached the stairs to the rooms of the motel, she turned towards Dean, who looked as if he were about to embark on a mission to climb the stairs of the Empire State Building all the way to the top. With a smirk, Jo grabbed Dean by the arm of his infamous leather jacket and tugging him lightly as she stepped upwards on the first step.

"Come On."

She tugged him up the stairs and heard the gentle scraping of his hand against the raining. Dean was enjoying the view from behind more that he was paying attention to the stairs. Hell, he had never thought of Jo as a true hunter. Not when she was being so non-hunter like right then. It wasn't the facts that Jo wasn't capable of being a hunter, because she definatly was, but she hadn't grown up in the life, hadn't had to live on the road, and she had had a chance to live a life. Dean was one of those people who believed if you didn't grow up in the life, you weren't meant to do it and shouldn't if you didn't have to. But Jo thought differently, the exact opposite in fact. She didn't care if she were born into that world or not. Her Dad was a hunter and she was going to follow in his footsteps no matter what her mother or any other people were going to tell her.

When they were safely up the stairs, Jo let go of Dean's arm and reached for her keys as they neared her room. She didn't know what room Sam and Dean were staying in, and wasn't going to ask.

"So," she said, sliding to a stop and unlocking her room's door. She turned to him.

"So," her replied, casually glancing over her body as if it were a perfectly normal thing to do, which in reality for him, was. "You goin' to invite me in?"

Jo's brow shot up, curiously.

"Why? I'm not some piece of ass, you know," she joked.

As her arms crossed, she realized that even with so much liquor on Dean, it still wasn't stopping him from hitting on her. It simply just made it easier. Dean snorted and leaned against the wall beside of her room's door.

"It would only make you a hospitable host, Jo," he said, a grin tugging his lips upward.

Dean knew he wasn't being coy whatsoever, but he was still hoping she'd go along with it, after all, he had gotten her to drink with him.

With an almost-amused half-laugh, Jo uncrossed her arms and pushed the door open.

"Have at it, Mister Hospitality."

Dean's brow quirked. Usually, he would have given her a smart-ale remark or some sort of response, but instead of being a dick, he stepped right on inside, flipping on the light switch as he did.

"Nice digs, Jo," he said, taking a glance around the near-bare room. She shrugged and moved past him as the door shut. She obviously didn't want to go into anything personal with Dean.

"It's a place to sleep," she said, peeling off her jacket.

Dean pursed his lips as if her were thinking. He wasn't sure about something. Usually, he had to try to get into a girls room, even if they were drunk. Dean had just asked a simple question and Jo answered the way he wanted, and stepped right on in. But he knew that it wasn't going to be easy with Jo. Heck even if he had a chance with Jo, he wouldn't get past her whole "self-respect" bit, which he respected for the most part. Sober. Right then, he couldn't tell the right ideas from the wrong ideas; he was acting purely on cheap alcohol and what adrenaline was still left in him.

"What," she asked, turning to catch Dean's eyes on her, for the dozenth time that night.

"What," Dean asked, mentally swearing at himself for not coming up with something better than to answer her question with the same question.

Jo's brow quirked upwards. She moved towards him, tossing her jacket onto the bed. His face was shadowing something, some feeling or thought he wasn't sharing with her. Jo's stomach fluttered, but she ignored it. She wasn't going to have these feelings, urges, while under the influence.

She frowned softly. It might have been easier to say something if her breathing wasn't acting abnormal instead of hitching as he looked at her that way.

Clearing her throat, she says, "If you're planning on working your magic on me, you better do it before I pass out."

Dean simply grinned.