Damn, did he miss you.

Working with you on those hunts was one of the most enjoyable experiences he had had in a long time— and that is saying something. He wasn’t one to have anything remotely kind to him stay in his life so when you did, he snagged that chance like a fat kid getting the last cookie.

“Hey, uhh, it’s Dean. Dean Winchester,” he started, talking into the phone as he left you a voicemail. “We worked like a month back together and I was wondering if you’d wanna come up to Chicago to help me out with a case. It’s a friggin’ wreck over here.”

He had debated this a few times, not wanting to bother you but the feeling of longing for a human connection that wasn’t Sam or hookers was hard for him not to deny.

“Don’t feel pressured to come up here or anythin’, just askin’ outta pure curiosity,” he said, sighing through the phone as he held it up to his ear. “I jus’ think you’ll be valuable to this case . Anyways, don’t be a stranger.”