"The first time we'd met, my Dad had just died and that... wasn't a real good time, as you can imagine. Not to mention your mother was in the same room almost every time we were together." Talk about a mood killer. Not that he hadn't been about to flirt with Jo anyway, until he thought better of it.

Dean takes a sip of his own drink, giving himself some time before the next part. "We've only kissed once and that was when she was dying."

Before she and her mother bought them time to get to Lucifer without hellhounds on their asses.