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They hadn't met normally, accidentally bumping into each other, or even at a small coffee shop, maybe in college or high school. Normal wasn't in the Winchesters vocabulary though was it no that was for sure but how they met was certainly a story for the grandkids.
Dean had been in hell. Hell of all places was probably the least romantic of them all but it's the gesture that counts. Right?
Castiel a real live angel of the lord had come down from heaven to save Dean of all people. Or at least that's how Dean saw it he felt he was filth and sure he maybe enjoyed torturing a bit but he knew it was wrong and that he shouldn't be saved.
That of course wasn't how Castiel saw it. He saw a mission to save the righteous man and there was no doubt in his mind that Dean was that. His soul had shown brighter than any soul Castiel had ever seen before.
That is just one of there first meetings though because Dean doesn't remember any of this he just remembers hell and then waking up in a box his voice as course as sandpaper.
The first time Dean met Castiel was in that barn after what seemed like hours of waiting and painting sigil's with Bobby. From the start Dean was in denial that Castiel raised him from the pit out of the goodness of his heart.
So you can only imagine when this stranger that took you out of hell, practically branded you with his hand print, and burns out your friends eyes says he's an angel you won't believe him.
Even through all those layers I think Castiel saw a boy who believed in Angels because his mom used to tell him that angels were watching over him and saw a small piece of thanks inside because he had gotten Dean out of the pit and that's what got him to stick around a bit more than heaven was comfortable with, to eventually rebel and fall, and to slowly but surly fall for Dean Winchester.