The thing is that when Cas first laid a hand on Dean in hell he was lost, and not actually because "For the first time, I feel". Cas had felt before he knew Dean. We know this because we know Cas had rebelled before. Naomi tells us Cas never did as he was told—that Cas had a "Crack in the chassis straight off the line" (something Chuck later echoes in a rage).
Cas's rebellion is far older than Dean and that rebellion is a function of what he feels. Cas just doesn't get to remember feeling. Each time he does, he's stripped of the memory of it... but subconsciously he starts to understand it as something he must keep secret.
Can I tell you something if you promise not to tell another soul?
Cas is in love with humanity, and we conflate this with Dean because Dean is the narrative heart, and the subject of Cas's greatest love, and because the concept of humanity and Dean are so deeply linked they're almost one in the same. We are not at all wrong to conflate the two, but make no mistake—Cas is in love humanity.
You misunderstand me, Dean, I’m not like you think. I was praying that you would choose to save the town.
Cas calls humanity a work of art, and the camera pans to Dean sitting on the bench beside him. Dean represents humanity. Not just as precious works of art, but also because humans get to feel. Humans don't get lobotomized for feeling. Dean encourages Cas to feel. He encourages Cas to feel by asking him to—begging him to, and by feeling for others, and by existing and deserving to be loved himself.
Dean echoes free will to Cas like a call from the wild. He's the beauty of humanity. He's the liberation and beautiful terror of choice. The reason "You always have a choice" and "There is a right and there is a wrong here, and you know it" works is because Cas already feels, already hopes, already loves.
You were gonna help me once, weren't you? You were gonna warn me about all this, before they dragged you back to Bible camp. Help me -- now. Please.
The function by which Dean gets through to Cas is through Cas's own feelings and convictions. He gets through because Cas is "not a hammer, as you say". Cas has questions. Cas has doubts.
Cas is in love with humanity, and every time he remembers it, he gets packed off to Bible Camp and he forgets. But he can remember again. What it takes is a push. What it takes is a hand reached out in the darkness. The day Cas rescued Dean from hell, two people were saved. A hand clawed out toward Cas too, breaking through his own torturous prison and offering him escape. For the first time in a long time, he felt.
Dean's importance is that he touches Cas. He makes Cas remember. And he keeps making Cas remember. Through touch, through words, through the expression of his own affection for Cas and for others. Because Dean cares, Cas cares.
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Have we considered bees and moustache and 119 and prison could all be part of an elaborate prank conducted by Tin Minear, and the opening emergency will be something normal like a wildfire or another tsunami
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