The first time, it was you three. You pulled me out of Heaven, although that was a good thing, the Shadow who controls the Empty was tearing through it looking for me.
[ The first death was difficult. Painful, confusing, scary. The very end of it was peaceful in its acceptance and him simply letting go, but he wasn't sorry when they brought him back to Heaven. It felt like he could be there for their love, and he was glad they wanted him there. But that led them down the path that brought a lot of regrets. ]
The second time was the Grim Reaper so she could use me, the third time was also her but she did it as a trade with Sam. Neither of you could let me go, even when it was my choice.
[ This isn't unusual for the Winchesters. They've sometimes tried to let each other stay dead, but it never lasts. Eventually they keep fighting for each other and it's a cycle that Jack is now sucked into. He loves Sam and Castiel so deeply, and he understands why they love him too much to accept his choices, but it also means it has to start all over again each time.
But he is deeply interested in what Castiel has to say about his reasons for being afraid. He's surprised to hear that Castiel used Sam, because that would be near unforgivable for Dean, that he knows for certain. But he knows that Dean does forgive him. ]
I see now why you are struggling. You did the wrong thing. You hurt the people you love. You regret it deeply. Only they can absolve you. I understand. I know that they will though, Castiel. And that you deserve forgiveness.
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[ The first death was difficult. Painful, confusing, scary. The very end of it was peaceful in its acceptance and him simply letting go, but he wasn't sorry when they brought him back to Heaven. It felt like he could be there for their love, and he was glad they wanted him there. But that led them down the path that brought a lot of regrets. ]
The second time was the Grim Reaper so she could use me, the third time was also her but she did it as a trade with Sam. Neither of you could let me go, even when it was my choice.
[ This isn't unusual for the Winchesters. They've sometimes tried to let each other stay dead, but it never lasts. Eventually they keep fighting for each other and it's a cycle that Jack is now sucked into. He loves Sam and Castiel so deeply, and he understands why they love him too much to accept his choices, but it also means it has to start all over again each time.
But he is deeply interested in what Castiel has to say about his reasons for being afraid. He's surprised to hear that Castiel used Sam, because that would be near unforgivable for Dean, that he knows for certain. But he knows that Dean does forgive him. ]
I see now why you are struggling. You did the wrong thing. You hurt the people you love. You regret it deeply. Only they can absolve you. I understand. I know that they will though, Castiel. And that you deserve forgiveness.