The first time Dean Winchester hears the angel's name, he's at Pamela's. "Castiel?" He asks, his hands squeezing those gripping him. Dean doesn't trust the angel.
He doesn't trust Heaven's "plan" for him, either. It's all a load of crap they tell themselves to justify killing. He has more common sense than that.
He's seen creatures rip people apart, all because it was part of some "grand scheme" of theirs or someone else's. To be truthful, Dean hates it all. Life should be all black or all white, no in between. There are monsters, there are hunters, and a few of one group kill a few of the other group, vice versa, and everything's all fine and dandy.
But he doesn't always get what he want, does he? Never. So now take the giant mixing bowl that was once his life, dump out all the ingredients into the garbage and pile angels on top of it because who knew? Not fucking him. Sam wished it his entire life, it seemed, and now look at that. Another jackass species threatening his brother's life.
Yippee.
"Dean, I would give anything not to have you do this." Yeah, that's a load of bullshit and they both knew it. It doesn't take a genius to figure out that it was the angel's that let Alastair free. He wants to think it was Castiel, because he doesn't trust the guy, but then the stupid blue eyed angel gives him that look, and Dean brushes it off with a "yeah okay."
No matter how hard Dean wants to think, to believe that Castiel is just another soldier, he's starting to realize it's not true. The guy is so... different, especially from all the other junkless dicks they've come across. It's not just because they're Heaven's (and Hell's) vessels; no, it seems as if Castiel actually... enjoys them. He sticks around, that much is true. It was proven when Dean looked at that photo in 2014 and realized that all those years passed and Cas was still there, with Dean. He may have been broken beyond repair then, but, hey, so had Dean.
When Dean turned his back to Castiel and told him "we're done," he didn't know who it affected more; the angel, or him. Yet then Cas had to go and show prove Dean wrong; he wasn't just a hammer. The "hey assbutt!" and dying part pretty much drove that home. God had a plan for the two of them.
He just hoped it was a better one than all the others they've had.