Set during Season 2, after John's death. Dean and Sam spend few nights around the roadhouse looking for a case, the rest pretty much follows on :)

Dean glanced across to the girl leaning against the bar at the roadhouse. She and Ellen were having what seemed to be a friendly conversation, but he'd never seen her before. She had a small thin black band around her wrist and a silver pendant on a necklace swinging forward from her neck as she bent over the bar, clutching a glass of what Dean assumed to be whiskey. She was slim and her long dark hair fell about an inch below her shoulders. In this light it almost looked as though her hair had a shine of purple about it.

"...Police seem to be getting nowhere with the case, I mean, why would they? They don't have our eyes. So I thought... Dean? Dean are you listening to a word I'm saying? ", Sam's voice drifted into Dean's pre-occupied mind and he realised he'd just zoned out on an entire conversation.

"Sorry. What were you saying about the police?", he mumbled, dragging his eyes away from the tall girl in battered black biker boots.

"Can you stop undressing girls with your perverted mind for two minutes and concentrate on finding a job?"

"Oh. I am so sorry. Can you stop whining at me for wanting a little time off once in a while?" Dean scowled as Sam huffed and threw the newspaper he was holding down onto the table. He contemplated making a comment about the irritating bitchface Sam was pulling, but decided against it and instead drained the last mouthful of his beer.
"Another?" He asked, knocking Sam's almost empty beer bottle with his own. A sigh and a nod followed from his younger brother who had guessed that another beer wasn't the only reason why Dean wanted to go to the bar.

Dean licked his lips as he placed his empty beer bottle onto the counter, standing next to the girl in the biker boots and faded skinny jeans who's glass Ellen was re-filling with whiskey. Up close he realised her hair was actually purple, it was just a really dark purple. Usually he'd take time to try and determine whether a chick was a hunter or not, but even though her entire look screamed "I own a gun and kill ghosts in my spare time", the silver charm that was hanging around her neck confirmed it. It was an anti-possession charm, threaded onto a thin silver chain. His eyes drifted down her slim waist, not too skinny, but obviously toned from the grave digging and chases that a hunter's life was undoubtedly filled with. Her worn, faded jeans that were on the verge of tearing in certain parts were skinny fitting and were held to her waist with a black leather belt. Just as his eyes travelled to her ass his thoughts were interrupted again.

"Take a picture. It'll last longer", the girl said without shifting her eyes from Ellen, who smirked as she replaced the whiskey bottle under the counter. Dean cleared his throat and mumbled an apology.

"Two more?" Ellen asked, taking the empty bottle from the counter in front of Dean.

"Hm? Oh. Yeah, please", Dean nodded, rummaging in his pocket for money but finding none.

"On the tab?" She smirked, noticing Dean's disgruntled expression as he continued to rummage in the pockets of his jeans.

"No." The other voice made Dean turn away from Ellen. It was the girl who he'd stood next to, the one with the tight jeans and nice ass.
She flashed a small smile at Dean and passed a few notes to Ellen,"On me."

"Well, wasn't that nice of you", Dean smiled.

"The word I think you're looking for, is thanks."

"Yeah, of course. Sorry, thanks."
He nodded thanks to Ellen as well when she slid two more bottles of beer in front of him, holding out a hand towards the girl who apparently hadn't lost interest in him yet.
"The name's Dean Winchester."

"I know. You're kinda famous around these parts, Dean." She attempted to fight a smile, but lost the battle as she shook his outstretched hand.
"Jaiden. Jaiden Ashdown."

"Hmm, Jaiden...I take from your accent that you're not from around here?"

"England", she nodded as Dean finally released her hand and wrapped it around her glass, noticing an elderly hunter at the other end of the bar who'd had one too many and had made the mistake of trying to hit on Ellen.

"We know a few hunters from there, you might know them."

"Well, there's a fair few hunters in England. Believe it or not, they have demons and spirits all the way over there too."

"But you don't have that stuck up British accent."

"Well, aren't you subtle. Not all people from England speak like that, Dean", Jaiden grinned, mimicking an Oxford English accent. Dean subconsciously smiled that famous crooked smile that made so many girls melt. If Jaiden didn't know better, she'd have said she thought she saw him blush.

Another guy approached the two hunters and huffed as he removed one of the two beers that Dean had been holding.
"Don't worry Dean, I'll get it. Wouldn't want you to strain yourself walking all the way back to the table." Jaiden watched the taller guy as he walked back to where the pair had previously been sitting with a smirk on her lips.

"Meet my pain in the ass little brother", Dean sighed before taking a swig of his beer, making sure it was loud enough for his sibling to hear. It seemed that he had heard based on the fact that he turned around and made a face at Dean.

"Sam, I'm guessing?"

Dean frowned and studied Jaiden's features.
"Yeah, Sam. How'd you know about him?"

"Are you kidding me? I have my contacts. What don't I know about you guys?"

"Who're these contacts then?" He asked with a raised eyebrow.
Like he needed to ask. If she knew Ellen, Ellen had known John, hence she would now know everything Ellen knew. Within reason he hoped.

"You know Bobby Singer, right? And then there's Ellen. And Jo."
Dean hadn't expected her to know Bobby, but then again, Ellen and Bobby had been friends for years.

Ellen looked up and the mention of her name and shifted her gaze between Dean and Jaiden.
"I ain't told her nothin'. Don't go sayin' I did." She winked, before returning to the group of drunken hunters.

Dean's expression read "What exactly do you know about us?" and Jaiden's eyes fell onto her untouched glass of whiskey, biting her lip as she smiled a small smile to herself.
"Sam over there went to Stanford. Studied law if my informants are reliable. I know you'd do anything for your brother over there. You're from Lawrence, Kansas. You drive a black '67 chevvy impala, pretty sweet by the sounds of it."

"Because that's not weird at all... What else do you know about us?"
Dean's eyebrows were raised but Jaiden was quick to inform him she wasn't some deranged stalker, just a close friend of a friend. She knew what he was asking between the lines of his question. Did she know the personal, private stuff that as of late hadn't been so private?

"I know about your dad", she said quietly, only glancing up briefly to see Dean's expression turn into a combination of anger, fear and sadness. He'd silently put up a defensive wall the second the words had left her mouth, she could sense that much. "I'm sorry you lost him."

Dean nodded slightly to show he accepted the condolence, but that was his only response other than, "What else?"
Jaiden took a long breath, deciding whether to continue or not. The last thing she wanted to do was push away the young man leaning on the counter.
"I know...I know how you lost your mother too."
Dean exhaled shakily and placed his beer on the counter with an unsteady hand. It was hard to hear those words out loud, even after so many years. It was harder to hear them from someone who up until tonight, was a complete stranger to him.
"I'm sorry, Dean, I really am", she whispered, reaching out to place her hand on his arm, half expecting him to shift or move out of her way. But he didn't, instead he let her gently squeeze his arm as a sign of reassurance and looked up to meet her saddened green eyes.
"It wasn't Bobby or Ellen, before you start taking swings. It was John who told me. A long time ago."

"You knew my dad?" Dean asked quietly, his confidence that he was going to end up with this girl tonight had faded pretty quickly, and with it his whole appearance in her eyes had changed.

"I met him a few times. In here actually, he came through on a passing visit. I got introduced through Ellen and I ran into him again when he bailed me out on a hunt."

"Meaning?" Although Dean was pretty sure he knew what it meant. Lately he'd gotten used to people telling him how many people his father had helped and how many demons he'd sent back downstairs. It was funny how when he was alive, so many people had a bad word to say about John, even Sam. Now he was dead, everyone thought he was a hero. Everyone suddenly decided to see John's good side.

"I'm stood here talking to you all because of him. He's saved my ass a couple of times."
Jaiden drained the glass and left it on the counter, moving so she was stood infront of Dean, his back to the counter.
"It's getting late, I should give Ellen a hand before I turn in."
Ellen walked past the pair and retrieved the empty glass, telling Jaiden that she didn't need any help.

"You've had a rough day, you just go on upstairs." She smiled, rubbing a hand briefly over Jaiden's back before removing herself from the conversation as quickly as she had entered.

"Rough day?"

"Long story", she exhaled, too tired to go into the depths of that day's hunt. Needless to say, she had a few fresh injuries underneath her shirt.

Dean knew the feeling and nodded, changing the subject to another burning question he had on his mind. "You're staying here?"

"For a few nights, till I move on. So if you're planning on sticking around..."

"...I'll see you tomorrow night?" Dean finished, a flicker of a friendly smile on his lips. But only for a moment and then it was gone.

"I guess you will", she returned the same twitch of a smile. A mere formality seeing as neither of the hunters felt like smiling anymore. However, it wasn't a formality for Dean to lean down slightly like he did. It wasn't a formality for him to try and place a small, gentle kiss on her cheek, only for him to miss and kiss the corner of her mouth instead.
"Goodnight, Jaiden Ashdown", he whispered.

"Goodnight, Dean Winchester."

TBC?
I think I'm finally getting the hang of fanfiction .net :)
Please let me know what you think and if I should continue.
You've all been pretty awesome so far, so thank you! :)