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Does Dean know Cas loves him?

Oww, that question's hard on the feels! Okay... okay. Yeah, I think so. Dean's not unobservant and he doesn't lack empathy, so he must be aware on some level. I think he's hung up on not knowing what it could possibly mean for either of them - what the devotion of a creature like Cas could even mean in human terms.

It seemed like Dean stuck and held on the whole "angels don't have the equipment to care, and when they try, it breaks them apart" bit. When was that - season 7, while Cas was off in mental honeybee land? Dean couldn't possibly have held onto that once he saw Cas parenting Jack with such unconditional love, years later, but by then there was so much water under the bridge... too much they both should've done, and shouldn't have done, and did do but then never talked about...? I dunno. I think it just became too big to tackle by then. They never had the luxury of enough time without a crisis to even start.

I think Dean believes that Cas shouldn't or mustn't love him, for various reasons, so he avoids consciously dealing with it as far as possible, and mentally frames it as doing them both a huge favour. Dean's aware, but can't bear it and feels completely unworthy of it, is my take. He wants to protect the people he cares about, including - especially - from himself. The more losses they suffer, the more he doubles down on the self-blame.

In reality, even when he's in absolute torment, as he was while fully human, Cas actually does just fine with his developing emotions - he accepts them, for starters - but from where Dean's standing, from the fragmented parts of the story Dean witnesses, it looks like a long-running disaster movie in which Cas gets repeatedly broken down and diminished and punished for choosing the Winchesters.

Even for a man who started out faithless, having an angel willingly fall from grace and choose him over heaven, brethren, and actual god must be... so overwhelming. It must feel wrong to be the focus of something so big and incomprehensible, even if it wasn't his choice or his fault. Dean's not even close to deciding what to do with that big picture by the time Cas flat-out says, "I love you," and makes it so very, very simple and human.