"You are not the first demon that I have dealt with, Meg." He gave her a look of bewilderment at that, because he had, after all, gotten involved with Crowley when it came to trying to use the souls from Purgatory to give him that power he needed to take on Raphael. It wasn't his proudest moment, no, but it had been a point where he'd worked with a demon, knowingly. But the kiss on his forehead, it was something that was welcome. It was comforting, even if this deal wasn't about giving him comfort, outside of giving him the medicine that was meant to put him into slumber and make him feel better.
He watched her carefully as she opened the bottle and poured the liquid in, curious about how this liquid was so potent that it would make him feel better. He was taking her at her word, although she was going off the word of the man at the pharmacy. He assumed that it was as powerful as it was claimed to be and perhaps it was made for instances just as this, where someone felt as awful as he did.
"No, you are not just my care taker." He told her this immediately, when she threatened to put the medicine into the toilet. "I don't see where it would be effective to pour that into the toilet, however. It doesn't have a cold, after all." He paused a moment, as he thought of how to answer, because he wasn't sure what to say. She wasn't just someone who looked after him. She was someone he trusted, without question and wanted to be around as much as he was allowed to.
"I told you that I care about you and it's more than I realized at the time. I care for you more than I would a friend, like I do the Winchesters." He began to explain, knowing his words may be clumsy because he wasn't even sure of how to put it all into words and make her see what he felt, because he didn't truly understand the full scope of it himself. "And you are more than a friend." He would care if something happened to either of the brothers, but he would care more if something happened to Meg. The impact she had on him was greater than anyone realized. "It's difficult to explain."