"Awww, Sammy's seen me in jail before, and he'll see it again. Besides, Jo, I'm hurt, do you really think I'd get caught?" He'd swoop in and out like Batman, leaving the bar owner and the sissy boy surgeon nursing broken noses and heads cracked from beer bottle collisions, then dart out into the night. Perhaps he would be more like a ninja instead...
He reached for the bottle again, consoling himself with the fact that he would find out one way or another. Perhaps someone on the message board would know.
"Listen, Jo..." he paused, considering his words carefully before proceeding. "What you did for Sam, when he was a demon...I want to thank you for that. I know I wasn't here for him, here to help find him and make him Sam again...so thank you." It was about as close to emotional as Dean Winchester got, and, rather than the moment last too long, he took a larger swig of the alcohol, occupying his mouth for the moment so that he couldn't say anything further.