John leaves Dean again. Castiel watches as the young hunter works his jobs, making sure he doesn't die, watches as Dean becomes more and more worried about his father, who won't reply to any of his messages or phone calls. Dean's worry gnaws at him, and Cas can see it even from above in Heaven. He prays to Cas to send him a message, and Castiel wishes he could, but Michael would know if he did and he can't risk that. Castiel can't risk forgetting.
He knows where John is. He's almost certain he knows what the eldest Winchester is doing, where he is going. What he is hunting. The creature that killed Dean's mother. Castiel doesn't blame him, wants the creature that pushed Dean into this life, the life his mother did not ever want for him, punished.
Castiel watches as Dean looks for Sam, expecting his brother to jump in with him. Cas sees Sam's reluctance. Sam is happy, with Jess. He doesn't want to get involved. Castiel doesn't blame him either.
'Why can't Cas help you?' Sam asks. Dean's face falls.
'Cas is out, on mega big angel business. He can't help me. I don't have anyone.'
Castiel blinks away the tears that form when he hears Dean say that. Surely he doesn't believe it, knows that Cas would do anything if he could, but he has no choice, really. His hands are tied. He was given orders, and he has no choice but to follow them. The itch for rebellion becomes prominent again, but Castiel pushes it down, deep inside him where he hopes it won't be able to resurface from.
Sam and Dean go on their hunt. It goes well, which Cas is glad of. But something is wrong. He can sense it, he just doesn't know what it is. It becomes apparent when Sam returns and Jess is on the ceiling of their room, just like his mother was all those years ago.
Castiel wishes he could have stopped it. He should have noticed, should have been smarter. The Winchesters, they're cursed. Or so they believe. Everyone around them dies, or leaves. Castiel is in the second category. Only temporarily though. So he tells himself.
If only things had been different, Castiel thinks. Me and Dean could have met in different circumstances. Had something proper, instead of what we have. I wouldn't want to take away what we have, but I wish it was more. We could have met in a coffee shop, or at work. He'd have been a mechanic, fixed my car. Maybe asked for my number, asked me on a date. Dinner somewhere, and a kiss goodnight. Gone on from there. Maybe moved in together, who knows? Adopted a cat… the things we could have had… if only things had been different.
Castiel doesn't know it, but Dean thinks a lot about the same kinds of things. He doesn't want much; happiness for his brother, to remember his mother, and to have a normal happy life with someone he loves. With Castiel.