He should be even more pissed than he already was, but there was a point where Dean thought he was just glad Sam was at least being upfront with him. Even if it was, y’know, after the fact.

“So what’s she doing here?” Dean didn’t even know where to start. “Sam, you don’t think it’s a bit weird for a demon to show up acting all buddy buddy? Dude, what if she knew I was gonna be okay?”

It made sense to him. From what he understood, he was something of a catch to the crossroads demons and they were probably keen on keeping an eye on him and his contract and okay, so he didn’t read the fine print. How did you work out what having a contract twice meant? Or apparently dying like he was supposed to, according to Sam’s version of things. Christ, it made his head hurt trying to work this out. Dean pretended like he was checking out the totally fascinating options of slop, slop and more slop, keeping his voice down to a hissing whisper. The sad thing was he couldn’t blame Sam for having a hard time keeping his head on straight after he supposedly died. It wasn’t like Dean had done much better after Cold Oak.

He didn’t even want to think back to it. Just remembering that empty feeling, Sam lying there? It still scared him, way way more than Hell ever could.

So yeah, he thought on some level he understood where Sam came from. It was the whole demon thing and their bullshit mind-games he was struggling with. It didn’t help that demon bitch had stuck to her guns on this whole thing either