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Summary
Dean lets himself enjoy Jack's heaven for all of two days before he grows restless. Meeting Castiel again is all he can think about ever since Bobby told him that the first thing Jack did after arriving in heaven was to bring Castiel back from the Empty. In fact, he went as far as thoroughly disintegrating the embodiment of the Empty, making it just a place where dead angels and demons go. Well, at least the ones who want to permanently sleep forever.
So Dean can't help but pray to Castiel and ask to see him, and the angel comes to him as soon as he can, as he always has.
Now that he doesn't have to save the world or run from ten different things anymore, Dean finally thinks about that twisting pain in his chest every time he sees Castiel or thinks about him, even in heaven.
Maybe he can truly be free now, so he gives it a try.