While Dean can think through that logically enough; acting on it is a whole different ballgame.

Getting over the hurdle of starting is going to the roughest, his gaze flicking back down to take in the sights. How is he just supposed to jump in on this? It isn't exactly like he'd had practice with someone other than the Devil which somehow makes the act of opening his mouth significantly harder. And to think, all he wanted to do is talk. Now he can't even crack a grin.

Leaning in closer, Dean dares himself to go for it, to get it over with, to just fucking do it. His lips even part, finding himself breathing significantly harder before he just goes and clams up.