A/N This is a slight AU, taking place during s5, while Sam and Dean are separated. This story will mainly focus on Sam, my OC, and his other ventures in the time that he and Dean are seperated and Dean is with Lisa and Ben.

Disclaimer: I do not own Supernatural. I only own my character, Chloe Jamison (portrayed by Logan Browning, respectively).

Chapter One

Vermilion, Ohio

Sam Winchester steps into the bar, the overwhelming scent of sweat, smoke, and alcohol all laced together instantly greeting him. "Photograph" by Def Leppard plays on the overhead speakers as Sam makes his way to the counter, sitting down on one of the plush chairs.

A petite woman with light brown skin, coily, ebony-colored, shoulder-length hair, wearing a tight black short-sleeved T-shirt and short shorts walks toward Sam and leans over the counter.

"How may I help you?" A thick Mid-Western accent laces her soft voice, with a cute face and pretty grey eyes. She looks tired and sweaty. Her nametag reads CHLOE.

"Uh, a whiskey," Sam says, clearing his throat and folding his arms over the counter. "Please." He usually hates the taste of whiskey. But tonight, he needs it; he needs something that will give him a long-lasting buzz.

Chloe nods, turning to the row of bottles on the wall behind her, pouring whiskey into a small cup. "One whiskey, comin' right up," she announces, sliding the cup toward him.

"Thanks." Sam gratefully takes the cup from her and tentatively sips it, then places it back on the countertop. "You look tired," he remarks, looking at her.

Chloe laughs hollowly. "You have no idea," she says dryly, her shoulders taut. "If one more old white man yells at me, I swear I'll lose my shit."

Sam doesn't know what to say to this, instead looking down at his cup.

Chloe tilts her head to one side. "You're obviously not from around here," she says observantly, putting her arm up to her face and resting her chin in her palm.

Sam's head jerks up. "How did you know?"

"Well, for one thing, you like a little lost puppy wanderin' in." Chloe smiles playfully. "Anyone would notice."

"Is it really that obvious?" Sam has always been shy and soft-spoken, but he didn't realize his hesitant demeanor was so noticeable.

"I wouldn't be sayin' it if it weren't," Chloe replies, shrugging. "What are you doin' 'round these parts, stranger?" She mimics a stereotypical cowboy twang.

Sam rolls his eyes. "I just needed to get away for awhile," he admits, smiling smally.

Chloe nods. "God, I hate this job," she grumbles, sighing and tucking a strand of hair behind her ear. "But I've gotta work somewhere."

"Why here, then?" Sam sucks down the rest of his whiskey, the spicy liquid leaving a burning aftertaste in his mouth.

"I'm in college," Chloe states, taking the cup from him and wiping down the counter with a grey cloth. "Not that many options around here for college kids, unfortunately. So I'm stuck working in this pigsty." She scowls in disdain and pushes the cloth aside. "Why are you here?"

Sam hesitates before saying, "Family issues."

"Ah." Chloe nods understandably. "Family drama, right?"

"Always," Sam replies, his mind drifting back to when Dean left him for Lisa and Ben. Lisa, the yoga instructor who he had a one-night stand with back in 1999. Somehow, it struck Sam as odd that he'd choose a girl who he knew for only less than 24 hours over his brother, who'd been there for him thick and thin, and literally even in death. Whatever. That was Dean's problem, not his. That is, if Lisa is dumb enough to take Dean in. Good luck with that.

"You look like something's eatin' you," Chloe remarks, not unkindly. "What's up?"

"Oh, um, nothing." Sam shakes his head, his bangs curtaining his eyes. "Just….a lot on my mind, that's all."

"Yeah, I get it." Chloe nods.

"Chloe!" An older guy with a bald, shiny pale head sticks his head through the door in the back. "Get back to work! This isn't social hour."

"Okay, okay!" Chloe yells over her shoulder, then rolls her eyes at Sam. "Hey, um, I'd better get back to work before Joe kicks my ass, but I get off half an hour. You down to hang out?"

"Yeah!" Sam clears his throat. "I mean, uh, yeah, sure."

"Great!" Chloe smiles. "Meet you in the parking lot at nine?"

"Yeah." Sam glances at his watch, which says 8:30. "Meet you then." His voice is slightly slurred from the alcohol, and his face is flushed. The song on the overhead speaker changes to "Nothin' But a Good Time" by Poison. "Uh, my name's Sam, by the way."

Chloe smiles. "See you then, Sam." She waves, then turns to the other customer sitting at the other end of the counter, preparing for the next round.

Chloe is relieved when Joe finally says she can leave. Her head is pounding, and her mouth tastes dry and sand-papery. She goes to the women's room and changes from her work clothes into a Led Zeppelin T-shirt, baggy, ripped jeans, and black combat boots. She ties her red-and-white flannel around her waist, then turns to the sink and splashes cold water on her face before walking out the back door into the parking lot. Chloe wasn't expecting Sam to stick to his word, with how many guys have used her or stood her up at the last minute, but there he is, leaning against the wall. He's cute, she has to admit, with his boyish, pale face, framed by chin-length, shaggy, mousy hair, and teal eyes tinged with a hint of hazel flecks. He's what her mother would call "easy on the eyes." It's really not fair how hot he is.

He's wearing a grey and blue flannel, loose, faded jeans, and brown boots.

"Sam!" Chloe jogs over to him, nearly tripping over her own feet.

"Whoa." Sam laughs. "You okay?"

"Yeah, I'm fine," Chloe drawls, reaching into her pocket and pulling out a pack of Marlboro cigarettes. "My mama tried puttin' me in ballet to correct my walk, but I even failed that." She laughs, lighting a cigarette and putting it in the corner of her mouth.

Sam raises his eyebrows. "You smoke?"

"Yeah," Chloe replies, her voice slightly muffled by the cigarette. "Don't you?"

"No." Sam watches her blow a smoke ring. "Never saw the appeal."

Chloe shrugs. "To each their own," she says nonchalantly, flicking ashes onto the pavement near her feet. "I've been meanin' to quit, but just as I try to, life gives me another reason to have another." She inhales and stares into the distance toward the forest not far from the parking lot.

Sam can't tell if she's joking or serious, so he decides to change the subject. "How long have you been living here?"

"All my natural born life." Chloe blows another smoke ring.

"Do you like it?" Sam asks, leaning back against the wall.

"Hate it." Chloe shakes her head. "Can't wait to get the hell out of this shithole."

"It's really that bad?" Sam's heard nothing but good things about Ohio, from the food to the culture, so her disdain comes as a surprise to him.

"You've no idea," she says, looking at him intently. "It's not what you think it is, at all. We've got a bunch of hillbilly rednecks and trailer trash around here."

Sam winces. "Ouch."

"Yeah." Chloe drops her cigarette on the ground and stomps it out. "Why do you think I wanna get the hell out of here? This place sucks. That's why I'm gettin' my degree in music, leavin', and never lookin' back."

Sam is intrigued. "Music?"

"Guitar," Chloe elaborates, folding her arms across her chest. "Been playin' since I was 6 years old. Taught myself. But my mama thinks it's a silly pipe dream that I'll never accomplish and that I should be in nursing school."

Sam laughs. "What?"

"Right?" Chloe tosses her hair and smirks. "But what she doesn't know is that the more you tell me I can't do somethin', the more it makes me wanna do it."

They continue talking into the night, from everything to nothing. Even though he's technically only known Chloe for 2 hours, he feels like he's known her forever. Something about her is comforting, familiar.

But still, like an enigma Sam has never known before.