Why did you have to get stuck with Ruby of all people?

It had been a long day of hunting, and Sam and Dean had left you alone with Ruby in this dingy motel room. You were sitting at a small table, surrounded by scattered lore books and notes, catching up on new stuff for possible cases while Ruby was lounging on the bed, flipping through the channels on the TV, her eyes glinting with mischief.

“You’ve been quiet.” Ruby hums, startling you with her sudden presence as you look up from all the books you have open on the table, clearly deep in focus the way you were biting your lip, her hand resting on the back of your chair. “Did I scare you?” Ruby has that trademark smirk on her face, and she was clearly pleased with herself.

“C’mon, loosen up a little. There’s so much better stuff to do than catching up on lore.” She knew you were doing this for possible cases because you guys were always on the move, but you could let loose once in a while, couldn’t you?