Eileen is just living her best life
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So, the first thing that happens is Castiel comes back.
"Right," Dean says eventually, gruffly. He looks down at his shoes. "I'm not gonna tell you how to live your life, man. It's—you know, yours. Do your thing, love who you love, whatever. I can't really stop you from loving me, if that's what you've decided to do, but I don't—I can't—"
"I know," Castiel murmurs, still just smiling a little, not looking heartbroken at all. "Don't worry about it, Dean, that's all I ask."
"So we're—" Dean risks a glance up, swallowing thickly. "We're good?"
Castiel hums. "We're good."