The first time Dean meets Jo, she makes him a sandwich. His dad is in the bar, talking to Ellen and even though he's been helping John out on hunts since he was twelve, he gets sent into the kitchen to wait.
"Have Jo make you somethin'," Ellen says, opening the kitchen door and shooing him in, "You look like a damn rail."
There wasn't anyone in the kitchen, so he takes a seat by the door and tries to listen in on the conversation happening on the other side. The sound from the bar is too much, so he gives up and starts to count ceiling boards. Gets up to 43 when a girl comes barreling down the stairs, skipping the last two steps and coming to a halt. A wide-eyed look flashes on her face for a moment, before it changes to an unimpressed half frown, one hand placed on a popped hip, the other holding a Walkman. The girl pulls off the chunky headphones, letting them dangle around her neck, and looks Dean over.
"You Jo?" He smirks, slouching in his seat and digging his hands deep in his jean pockets.
"Yup." She could be anywhere between twelve and twenty (he learns later from his dad that she was much closer to twelve), dressed in shortest pair of cut-offs he's seen outside of Dukes of Hazzard reruns and a faded AC/DC t-shirt that rides up on her hips. "Bet my momma volunteered me to make you food?"
"Something like that," Dean grinnes at her as she sways across the kitchen, yanking open the door to a gigantic old refrigerator. "I'm Dean."
"You're John's boy?" She pulles some containers out the fridge and Dean gets up from his chair by the door to sit at the scrubbed table in the middle of the room.
"One of them. Got a brother Sam." Jo slices off two thick pieces of bread and tosses them on a plate.
"Lucky," she snorts, slathering one side with mayo. Dean smiles and shakes his head. After a few minutes Jo sits down and places a monster of a ham and cheese sandwich in front of. He bites into it and swallows, his stomach growling appreciatively. He hasn't eaten since Illinois and its good to be on digesting terms with food again.
Jo doesn't interrupt him as he tears through the sandwich, only props her feet up on a chair and watches him amusedly. When he finishes, he pushes the plate away and gives a satisfied burp. To her credit, Jo just rolls her eyes like she's used to it and starts grilling him about life on the road. He's poised to tell her a really kick ass story about this medicine man they'd met in Baton Rouge when John marches in and signales to Dean that it was time to leave. Ellen follows him in, looking a little less than happy about whatever they've just finished talking about.
"Thanks for the sandwich, Jo." Dean gives her a smile and follows John to the door. Jo crosses her arms and half smiles back.
"Seeya 'round, Dean."
The second time Dean meets Jo, she's a lot closer to twenty than twelve, but is still too young for Dean to feel entirely comfortable with how her jean mini-skirt rides up when she sits down next to him on the hood of his dad's car. She kicks off her heels in the grass next to the wheel and pushes herself up off the bumper without spilling a drop out of the two beer bottles she's holding.
"Jo."
"Dean."
"Long time no see." He accepts one of the beers and takes a long swig. They had just gotten off a pretty rough hunt and Sam had gone off to college so he's grateful for the drink. Jo watches the beer go down his throat before taking a long drink out of her own bottle, tilting her head back and shaking her blonde hair over her shoulders.
"Aren't you a bit young to be drinking?" Dean smirks at her and Jo sticks out her tongue at him.
"Only when my momma's lookin'." He could swear she's said it a hundred times before in a hundred different contexts by the knowing smile she gives him.
"So how you been, Joanna Beth?"
"Shut the hell up, Dean Winchester," she scoffs, lightly punching him on the shoulder, "Bored out my damn mind."
He laughs and she scowls and they both drink.
Jo grills him again about life on the road, but this time it's not about the things he's seen but the things he's fought. Ever obliging, Dean tells her about everything he can think of, even the bad stuff because if she knows the bad stuff, she won't run off to find it (later he'll realize that this kind of logic doesn't apply to Jo). Dean watches the gears turn in her head and the mental notes being scrawled down as he talks over the mouth of his beer bottle. He's about to finish telling her a really kick-ass story about a banshee they killed in the Appalachians when the screen door slams a couple yards away and John Winchester stomps down the steps. Ellen is waiting on the other side of the screen door, arms crossed and eyes zeroing in on Jo and Dean.
"Shit," Jo mutters. She slugs back the rest of her beer, throws the bottle into the trees and gives Dean a peck on the cheek. She slides of the hood of the car and grabs her shoes off the ground. She's sprinting one way across the gravel while his dad is making long strides the other way. "Bye Uncle John! Thanks for the stories Dean!"
The third time Dean meets Jo, she doesn't have a sandwich or a beer or a willing bed for him (it's the next logical step in Dean's mind, but as before, logic doesn't apply to Jo). Instead she has a shotgun barrel pointed at his chest, something that is surprisingly normal for a Winchester/ Harvelle interaction. Later, when all the guns get put down, Ellen reintroduces them for the second time and then goes to explain it all to Sam.
Jo doesn't ask about the past six or so years because she's sort of forgotten how many it's been. Instead they swap stories of the past couple months, what they can remember and what they can share. He's about to tell her about the vampires when a door swings open and he half expects his dad to come barreling through, telling Dean to stop flirting with a girl young enough to be his baby sister and get in the damn car. Instead Ash busts in and they have to get to work.
When the job is over, Dean and Sam come back to the Roadhouse and he gets another chance to sit with Jo. They both pretend not to remember meeting already twice, but when she sits down next to him, her knee miraculously finds his under the counter and later her cell phone number finds its way to his speed dial.