Because he never had to worry about his appearance in the past, Castiel never really put much thought in how he looked, especially in situations like this. To not keep his trench coat on as a security blanket, that had been a huge step for him and deviating from the clothing he was used to wearing, that was another. His sleep wear wasn't much, but it was proof he was slowly making changes. If sleeping in the first place wasn't already a sign of that. Angels didn't require sleep, but humans did. And in that first couple of days Castiel tried to resist sleep, only to succumb to it because his body actually needed it for function and putting up that fight was only harming it.
"You asked someone in town for help?" He was curious about this, because she didn't turn to Sam and Dean for it. He understood why, with her recent injuries at the hands of one of their own, but he also would have thought they wouldn't bring in too many others not already involved, especially outsiders, to aide in keeping him alive. He would have to think this boy in town, to show his gratitude. He wasn't sure how humans did that, because most of their rituals were still a bit confusing or archaic to him, despite how he'd observed them for a great deal of time.
Castiel eyed the plate of food she'd prepared, a hint of a smile forming along his features, one that he rarely showed but was genuine all the same. She cooked for him. It wasn't something she had to do and she had no reason to enjoy the food herself, not for sustenance at least, but she did it all the same. She was still his caretaker.
Experimentally, he took a piece of the bacon and chewed at it for a moment, almost as if he were analyzing it. Trying to take in the taste and decide if he liked it.
"I like bacon, almost as much as I like burgers." And that was a great deal, as a point of reference. It almost made him want to share some with her.