AU. Sometime season 2. AU.
Jess didn't really know what she expected of this road trip. Her friends promised adventure and fun and freedom and it was her senior year, so why the hell not, right? She didn't really know what she expected.
She definitely never expected to see him again.
It was hard finding a back road bar where four girls could spend the night, have fun and be safe. They didn't really thought that part of the whole 'lets-just-go-where-the-road-takes-us-no-plans' thing. But this bar was supposedly owned by a woman and her daughter and as shady as it looked on the outside, it would have to do for tonight.
They walk in, get themselves a table and Jess is just about to sit when she hears it.
Her heart almost jumps out of her ribcage at the name. Her friends all turn to her as she scans the room towards the man being called…
… and it's not him.
He's pretty, though. But not him.
The blond man turns around looking annoyed to the wiry, very weird looking man calling out for him.
"I thought you said we were going to play some more…"
'Winchester' chuckles. "We are, Ash. I'm just grabbing something in the car. Sammy can keep you entertained till I get back…"
She follows the man's nod to a table in the back. There, looking down at some papers, he just waves a hand, not even looking up. "Yeah, Ash, come here… could use your help, man."