Not always rainbows and butterflies
One Shot
Summary: And, at the end of a not very interesting day, Jo Harvelle met Dean Forester.
Disclaimer: Jo belongs to Kripke, Dean to Amy Sherman-Palladino or something... Title and (pretty much) the last sentence were shamelessly stolen from Maroon 5.
Author's Note: I- I really haven't a clue where this came from? I think I thought, 'well, gee, there's plenty of gilmore girls/supernatural crossover fics out there. But what about the some secondary character interaction?' and then this came into being.
Genre: Romantic Angst
Characters/Pairings: Jo Harvelle, Dean Forester. Ellen, Sam and Dean make special appearances as well!


Jo just turned seventeen when the cool clouds of autumn rolled in, and he rolled in with it. She knows from the second he rolls in that he's not from around her parts- the sheen of his blue pickup is only hindered by the light dusting of dirt and miles, and isn't completely taken over instead by mud and back water dirt. But the tired apprehension on his face is what makes her think that maybe he isn't so haughty after all.

When she finds him again, he's sitting at a small table in the back of the bar, staring at the empty pool table. She walks up with a smile, tapping a beat on her pad with a pen, and when she asks what his poison is, he replies "brown haired girls with their noses in books and Rosemary's Baby on the mind". She pours him water because he's not old enough to drink but lets a splash of gin settle in the translucent liquid. By the way he looks, he's known alcohol, and he looks like he needs it.

She sits down at his table and he tells her about a girl, a girl named Rory, who he loved for four years, who he had his heart broken by twice, and who he had ruined his marriage for, only to have his heart broken again.

He says he had to leave the tiny town he had lived in for four years, to go out to college. Says a small college in California was open to him, and he decided to drive there instead of flying, because this way at least he could clear his head. Jo listens to him speak and watches his pain filled eyes get only worse the more he relates. She clutches his big hands in her own, lets him go on and on without interruption. She's only the audience, the one thing he had been looking for, the last thing he thought he wanted.

He downs his drink in one swallow and stands, and she jumps to her feet to look up at him earnestly. Where do I pay, he asks, and she shakes her head, you don't pay here, not today. She pulls down on his shoulders and kisses him hard on the lips, whispers against them that she hopes he'll find everything he's looking for, because he's good enough, dammit, and he shouldn't be told otherwise. Richard and Emily Gilmore be damned.

He curls large, unsure hands over her back, winds the left through her hair as the other massages at her waist. When I do, he says, shifting the raw eyes onto her, I'll be sure to come and find you. She kisses him once more before he leaves out the front door, ignoring her mother's disapproving eyes and the interested barflies. She hears his truck rev away, back on the road again, and she slips a five dollar bill out of her apron and pays for his order herself.

Dean and Sam Winchester find their place in the bar four years later, and the first time she ever sees Sam she nearly grins large enough to crack her jaw. "Dean?" she asks, but the shorter one looks up at her and asks, yeah, sweetheart?

She tries to not let the pain of her unexpected joy roll on over her. She instead closes her grin and leans against the bar. The boys have guarded, pain filled eyes, and she goes to them. She has always been a sucker for the broken smiles.