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Dean was broken. Cas knew that, but he was broken too. Everyone was a little bit.
So Cas hadn’t taken Dean’s ‘I’m too broken for you’ to heart. He’d used as encouragement to show that he could fix him. He could make Dean feel like he wasn’t as broken as he probably was. Cas knew that the source of all Dean’s cracks and chips was trust. Dean felt he could only trust Sam and Cas, he had been let down way too many times. Cas remembered, all too well, how long it had taken Dean to trust Cas. It had frustrated him to no end in the beginning but once he had gained said trust, he realised that he was lucky.
Unbelievably lucky, and he wasn’t about to take Dean’s second refusal, along with a ‘When Harry Met Sally’ analogy that he didn’t understand, to heart. Instead, he watched the movie and he smiled from ear to ear at the ending. It took two weeks of following Dean like a puppy-he normally did that anyway?-and Sam smirking every time they walked next to each other for Cas to realise that Dean wasn’t turning Cas down so he didn’t hurt himself, it was so he didn’t hurt Cas.
Dean had said, during an argument about vampoul or ghoulpire, “And what happens in a hundred years, Cas? When I’m dead?”
Cas didn’t listen though.