The sad fact was, it was, just this. She needed him to understand her, she needed to know from him, that once she'd been a shining beautiful thing, that once, she'd been there for him. That once he'd needed her. But he had no memory of that night, of their time together and he didn't want it back. He'd made it very clear. So there'd be no affirmation for the angel who was slowly losing herself in her own mistakes. She was falling, because of a demon, because of the King of the Crossroads of all things, and it was hard to fathom how it could ever get any worse than that.
But Anna knew it could.
"Its not because of you Dean. Not me anyway. There are reasons why I'm falling. Things I've done that maybe I could have told you if you'd taken the memories back, but I can't, not like this, you'd never understand it. And I'm sorry I did things this way. I'm sorry I came in here. I have no right. It's just what it is. It's just how I thought it had to be. You're with her out there. You're happy. And I'm not gonna do anything to disrupt that, you have a right to be happy. More than most of us do."
He was guilty, he felt so much guilt, over her, over Castiel. Over Sam, over every single person in his life. For breaking in the pit, but Anna couldn't blame him. She'd never blame him, and she could see how uncomfortable all this was making the Hunter.
"I wish you'd dream easier dreams, I wish this was a refuge for you. But those memories you're holding on to, I can't take those away without destroying another part of you. You've lost enough of your memory already. So all I can do is hope that one day the guilt won't drag you down so much. It shouldn't. No one blames you Dean. No one else could have lasted as long as you did down there and lived with any measure of focus or sanity. You're strong, you're the strong one." And she'd always believe that, even if she'd come here for an entirely different purpose maybe she could help Dean find his way back.
"I'll go if you want, you can try and get some proper sleep. But I want you to know, none of this is on you, nothing with me, or with Cas. You focus on you and yours and we'll...it'll be fine. Okay? I promise"