Once Dean assumed Lisa was fully clothed, he looked back at her with concern, moving towards her as she sat and ignoring her hand wave to place his own on her shoulder with a quick whisper, "You alright?" He hadn't considered her, with all the talk of supernatural shit that she clearly wasn't used to anymore. With the way her head had been acting, he kicked himself for not being more careful with his words, but he was relieved a small door to his past had been opened. They'd been dropped in the meat grinder, and if they were going to be dealing with monsters on a constant basis, he couldn't keep those kinds of secrets forever.
It was actually not something he realized until Emma said it, how screwed they really were. This was their world, the ones that go bump in the night and creep out at you from the dark, this was their home turf. He was the outsider here. Him and everyone streaming in from all different dimensions...
It was a bit much to take in, and he suddenly felt that much worse for dumping even more crazy information on Lisa. Sure, he'd dealt with travelling through time and space before, that was nothing to him, but even then it had all still been his own world. If there were other dimensions out there like the make-believe stuff he'd seen on T.V. why hadn't he heard about it? Why weren't the Angels all over that shit? A world where monsters spawned and humans were alien shouldn't be news to someone like him.
That was it, he had to get off his feet, separating himself from Lisa just enough to set his weight on the desk. "So... so you're from a place where magic is just a thing people just have?" His question was aimed at Emma, though it was just follow up clarification for his actual question. "How long've you been here, and how much do you know about... here?"