She had once pounded his face in just for kicks. She'd possessed his little brother, killed another hunter using Sam's hands while also almost killing Joe, tried to shoot him, beat him and Bobby up, had been guilty of so, so much more than that, and on top of it all was the daughter of the yellow-eyed demon the Winchester family hated with a passion…

And apparently his best friend's new crush.

Dean was having a hard time with this.

And it was worse because Castiel didn't even know it. He simply liked to have Meg around, even after he stopped being off the deep end crazy. They'd actually smile—the stoic, righteous angel and the I'm-too cool-for-this-shit , apathetically sadistic demon would actually smile—as they talked about a memory he and Sam were not privy too.

Dean was used to not knowing what the heck was going on with Castiel, but this was a whole other level.

Cas didn't even understand why he smiled or that him smiling meant anything more than the simple gesture.

But angels didn't smile, and demons most certainly didn't either. Unless they were killing someone or inflicting some kind of pain.

And Meg was smiling as she patted Cas's head mockingly, calling him another stupid semi-insulting name and reminding him he was too naïve and stupid.

And Cas just smiled and nodded, looking slightly confused but taking her word on faith like he always did.

Stupid angels.

Damn demons.