Dean's patience is so dry already that it's the Sahara desert, and if this look could kill demons, it would've taken out Abbadon.

"Yeah, I'm familiar with the particulars. You working your way up to a point? 'Cause I know how this story ends already."

He's really almost afraid of where she's taking this, if only because he's trying to figure out from which angle she's trying to hit him with a low blow. That's what this is about, right? Reminding Dean of that shitty ass time that fucked him up for a year? Like, worse than Purgatory because at least he learned something out of that?