It was a cold bleak night, stars hardly speckled the light polluted sky.

You walk to the alleyway behind a bar, Hellfire ironically enough.

You weren’t proud of what you were doing. Ruby was on hiatus with the Winchesters. She screwed up, they don’t trust her right now. You do. At the very least you find her useful.

You need info on Lillith, Ruby says she has it. Whether thats true or just a ploy to see you again, you don’t know. Do you show up anyway? Yes. Yes you do.

“Hey sly guy. You tell the Winchesters we’re still meeting yet—?” You cut her off with an aggravated glare. You didn’t appreciate her making you feel even guiltier you were here.

“Sensitive. I get it.” She says with a devilish smile and shrugs coyly. She’s stalling. You’re here for information. That’s it. No other reason…you don’t trust her…you don’t even like her…

Definitely.