Dean: "You okay?"
Cas: "Yes, but -"
Dean: "Good." [turns and walks away]
Belphegor: "Wow! Awkward. Wanna talk about it or... ?" [Cas walks away] "Is that a no? That's a no." 15.01
Even though he's still angry at him, and even though he walked away, this scene shows that Dean will always care about Castiel. He's mad, but still he cares, otherwise he wouldn't ask. This is love, because even though all Dean feels now is anger he still finds a way to ask Cas if he's ok.
And if you want to point out that right after Cas' answer he just walks away, which is not really caring, more like making sure he's ok enough to carry on, then you are wrong. There's hatred in Dean's heart right now, and he fights it. Can you imagine how hard it must be to push it away for a second? Just so he can ask Cas how he is doing? It takes a lot of strength.
Dean just walks away after Cas' first answer because it's hard, and Dean might feel like that if he kept talking more with Cas he might storm out again. Because he knows that Cas wants to talk about it, and he knows that if they talk about it again he might say something or do something he might regret later. So instead of hurting the person he loves again, he choses to walk away.
It is really a big gesture from Dean and we might not even realise it. As we know Dean does sometimes have anger issues, and when he gets in fight with someone (verbal or physical) it can get sometimes fatal. In the fist seasons we can see he doesn't really do anything about it, he just apologises later, or sometimes he doesn't apologise at all. But as he gets older he starts to realize that it is a problem and he's trying to think of a solution. Especially when he knows how he can hurt others, and especially when he's arguing with Cas.
Because its Cas, the only person that seen Dean's soul, and seen that he doesn't have to be just destructive and fatal as he thinks he is. He adores Cas for being with 'em for so long and for not giving up on them, especially not on him. And he doesn't want to loose him, and more importantly he doesn't want to be the one who hurts Cas so bad that it will be him who chased Cas away. And he wouldn't forgive himself for that. So this is beautiful character development, and it shows how much Dean cares.
Cas: "Dean, I recognize that I... dropped the puck."
Dean: "Ball. It's, uh... It's 'dropped the ball'."
Cas: "Ball, right. I didn't tell you about Jack, and then after what happened with your mother..."
Dean: "Don't."
Cas: "You're angry."
Dean: "Yes, I am angry. At everything. All of it."
Cas: "All of it?"
Dean: "This mess... all the messes. It turns out that we're just hamsters running in a wheel our whole lives. What do we have to show for it, huh? Tell me you don't feel conned. God's been lying to you, Cas, forever."
Cas: "You don't think I'm angry? After what Chuck did? After what he took from me? But that doesn't mean it was all a lie."
Dean: "Really?"
Cas: "Chuck is all-knowing. He knew the truth, he... he just kept it to himself."
Dean: "Well, now that his cover's blown, everything that we've done is for what? Nothing?"
Cas: "Even if we didn't know that all of the challenges that we face were born of Chuck's machinations, how would we describe it all? We'd call it life. Because that's precisely what life is. It's an obstacle course, and maybe Chuck designed the obstacles, but we ran our own race. We made our own moves. And mostly, we did well with that."
Dean: "Did we? I'll tell you what we do know. Nothing about our lives is real. Everything that we've lost, everything that we are is because of Chuck. So maybe you can stick your head back in the sand, maybe you can pretend that we actually had a choice. I can't."
Cas: "Dean. You asked, 'What about all of this is real?' We are." 15.02
Imagine Cas devastation when Dean told him he thought everything was a lie because it was all Chuck controlling them. He literally yells; "It wasn't all a lie!" And then Dean says: "Nothing about our lives is real." And Cas looks at him and then says: "We are" real. Cas knew. He literally knew so deep down, so deeply engrained in him, that how he felt about Dean was real. Against all odds, against everything pointing to being part of Chuck's plan. But not this. It could never be this. We are.
Cas meant this not platonically. Sam and Eileen litteraly had this conversation too, but they kissed. Castiel knew his love was real, because it hurt too much not to be.
Cas: "The plan changed, Dean. Something went wrong. You know this. Something always goes wrong."
Dean: "Yeah, why does that something always seem to be you?"
Cas [stares at him, stunned and hurt]: "You used to trust me, give me the benefit of the doubt. Now you can barely look at me. My powers are failing, and... and I've tried to talk to you, over and over, and you just don't want to hear it. You don't care. I'm... dead to you. You still blame me for Mary." [Dean nods.] Cas: "Well, I don't think there's anything left to say." [Castiel makes to leave.]
Dean: "Where you going?"
Cas: "Jack's dead. Chuck's gone. You and Sam have each other. I think it's time for me to move on." [Castiel leaves.] 15.03
[A phone rings in the bunker's war room, and Dean still in his dressing gown searches through a tangle of charging cell phones for the one labeled FBI, and answers]
Dean: "This is Assistant Director Kaiser."
Sheriff Roy: "Uh... This is Sheriff Alden Roy. Just checking on Agent Worley."
Dean: "Would you put my agent on the phone, please?"
Sheriff Roy [handing the phone to Cas]: "He wants to talk to you."
Cas: "Hello?"
Dean: "Cas. Sam's been trying to call you."
Cas: "I know."
Dean: "Did you check his messages?"
Cas: "Nope."
Dean: "Right. Smart. Why would you? Look, I don't know if you care or not, but, uh... God... Chuck... is back on the board, so watch yourself. And check your damn messages." [hangs up the phone] 15.06
Eileen: "Sit. Eat."
Dean: "No, no. Uh, nah, I can't."
Sam: "W-W-Wait, wait. Wait. You're turning down bacon?"
Dean: "Mm, yes, yeah, I'm actually... I'm gonna head out."
Sam: "Okay, fine. Just give us a second to wrap this up, - and we'll come with you."
Dean: "No, no, no. No. I'm... I'm... I'm good. You guys stay, eat. It smells terrific."
[Dean leaves the room, and Sam, concerned, follows him out into the hall]
Sam: "Hey, Dean. Dean, whoa, whoa, whoa, whoa, whoa. Just hold on. Slow down."
Dean: "No, I'm good. I'm good."
Sam: "You're good? W-What does that mean you're..."
Dean: "It means I got to... I got to get out of here, okay? I just... I got to... I'm gonna take a drive, clear my head."
Sam: "Alone?"
Dean: "Yeah, you know, you and Eileen, you guys are having fun. I don't want to spoil that, you know?"
Sam: "Yeah, go, go. Clear your head. Eileen and I have stuff to do."
Dean: "Yeah, I'll bet you do. Yeah? Hmm?"
Sam: "It's not like that. I-I-I meant looking for Chuck and Lilith and..."
Dean: "Sure. Got it. Um, okay, but if, uh, things go your way, just make sure you put the sock on the door so I know."
Sam: "Call me if you need me."
Dean: "Always do."
[Sam returns to the kitchen] Eileen: "Is he okay?"
Sam: "I think. After everything, uh, Dean was so... down I-I-I thought he wouldn't get back up again, but... but now, him leaving?" 15.07
Sam: "Cas? Wh... What in the world, man? Where have you been? I-I've been calling you and texting..."
Cas: "I know. I was... Well, it doesn't matter. I'm here now. I'm ready to help."
Eileen: "Hi."
Sam: "Yeah, uh, Cas, this is Eileen Leahy. Eileen, this is Cas."
Cas: "Well, where's Dean?"
Sam: "He went for a drive. He needed to clear his head." 15.07
[Dean slices his palm to add blood to the spell]
Cas: "Here. Allow me." [Cas heals Dean's hand, is visibly exausted after that]
Dean: "Thanks." 15.08
Rowena: "What am I picking up from you two? A wee tiff? Tell your Auntie Rowena."
Dean: "It's fine. Don't worry about it."
Cas: "It's fine."
Rowena: "Boys? Fix it. I don't have many regrets, but the few I do still haunt me. Making Napoleon so short was just bitchy. Telling Mick Jagger he had no future when I dumped him. And, well, everything with dear Fergus. Then one day, you die, you go to hell, and you can't make it right. So fix it!" 15.08
"I gave everything for him. I loved him." Michael to Dean and Cas 15.08
- "I gave everything for you!" Cas to Dean 5.18
Dean: "Adam, I want you to know we are sorry. What happened to you... You're a good man. You didn't deserve that."
Adam: "Since when do we get what we deserve?" [while looking from Dean to Cas, Cas breaks the eye contact, Adam/Michael nods knowingly] 15.08
Cas: "Well, this place will bring that out in you. Guilt. It was my fault the Leviathan got out. It was my fault we were here the first time. I carry that guilt every day."
Dean: "I know you're sorry, Cas. About Bel, about Mom."
Cas: "I was talking about Jack. I already apologized to you. You just refused to hear it."
Dean: "Sorry I brought it up. Maybe if you didn't just up and leave us."
Cas: "You didn't give me a choice. You couldn't forgive me. And you couldn't move on. You were too angry. I left, but you didn't stop me." Purgaotry 15.09
[Dean wanders the woods of Purgaotry, alone, desperately trying to find Cas.]
"Cas? Cas, I hope you can hear me... that wherever you are, it's not too late. I should've stopped you. You're my best friend, but I just let you go. 'Cause it was easier than admitting I was wrong." [Dean breaks down, sniffles, and then kneels at the base of a tree, crying] "I... Oh, I don't know why I get so angry. I just know... I know that it's... i-it's just always been there. And when things go bad, it just... it comes out. And I can't... I can't stop it. No matter how... how bad I want to, I just can't stop it. And... And I... I forgive you. Of course I forgive you. I'm sorry it took me so long to... I'm sorry it took me till now to say it. Cas, I... I'm so sorry. Man, I hope you can hear me. I hope you can hear me." Dean praying to Cas 15.09
Attention to what Dean doesn't say here. He doesn't say that Cas is family, for once. He's not hiding behind the pretense that family cares for each other and that's why he's doing what he's doing. This is just Dean and Cas, as two individuals. Two broken individuals who care for each other. It's so, so personal.
Dean really didn't know how to deal with his relationship with Cas until this scene. Of course he loves Cas and doesn't want to lose him, but he was unable to just go out and say it. He literally dug his heels in and kept mum until not saying it would mean that Cas would be no more.
With Sam he uses their familial bond as a scapegoat when he wants to make up after a fight. When Sam and Dean part ways Dean can just go right back and say "I'm pissed at you but we're family so we stick together" and he can keep Sam by his side without showing emotional vulnerability.
It just sunk in that he can't do that with Cas. He's tried to do it a couple of times by calling Cas family but now he knows that it doesn't work with him and he needs to literally confess. Dean always tried to downplay his dependence on Cas by calling him family too. In a "I don't love you because you're you, I love you because you're family and that's how it's supposed to be" kind of a way.
Dean had to strip bare and confess that he cared about Cas in order to keep him by his side and that was a very hard thing to do for him. Also he confessed to himself along with Cas. He forced himself to be vulnerable and show his real emotions, vulnerable in a forest filled with Leviathan too. That's a bit poetic.
Dean said more than once that everything felt pure in Purgatory. He never had to hide that the one thing he wanted was to be with Cas.
[Purgatory, Dean still searches for Cas. He checks his phone, only 00:02:56 remains on their timer]
Cas: "Dean."
Dean [turns to see Cas sitting at the base of a tree]: "Cas?"
Cas: "You made it."
Dean: "I made it?" [pulls Cas into a hug] "You okay?"
Cas: "I'm fine."
Dean: "What happened?"
Cas: "They were after me, not you. I figured it would be safest to give myself up."
Dean: "They take you to Eve?"
Cas: "Yeah. We were en route. I waited until I... saw this." [pulls a blossom out of his coat] "It got a little smushed." [Dean chuckles] "Once I had the blossom, I fought, caught them off guard. They fought back. I managed to get away."
Dean: "You did it. You did it, Cas."
Cas: "Well, they're still after me. We should hurry."
Dean: "Okay, Cas, I need to say something."
Cas: "You don't have to say it. I heard your prayer." Purgaotry 15.09
Cas literally has to silence Dean. It's not a Han Solo moment, not even close. The moment Cas is happy the Empty will come for him, so he can't listen to Dean lay his feelings bare in case it brings him happiness, too dangerous.
Sam [turns to see Dean nodding off in a chair]: "Hey, Dean, if you're tired, why don't you go to bed?"
Dean: "I'm not tired. I'm not tired. I'm just resting my eyes. I'm good." [Cas brings four bottles of beer into the library and sets them on the table] "Ooh. Jackpot." [Dean shuts his laptop and takes a beer from Cas] "Ahh. Thanks. Alright, well, I say let's call it, hmm? Movie night?"
Eileen: "I'll make popcorn." 15.09
Pinterest folder to season 15:
https://www.pinterest.de/april31415/destiel-canon/it-all-ends-s15/