Now there was the question of the century. Why? Why would she want to give Dean all the memories of the year he'd lost. The things he'd seen, the things they'd done together. And he was right of course, she was far from in love with him. She supposed it was more than showing him them together. It was a lot of things all rolled into one. It was knowing that once, he'd viewed her as something good, something to be relied upon. Perhaps even a friend, just like Cas was. And while he'd been rebuilding a friendship with Castiel, she herself had been running around the Earth with the King of the Crossroads and loosing everything that she'd once held dear just because Crowley smiled at her. What was wrong with her?
"I wanted you to remember me Dean. Properly, like people should remember me. The Angel of the Lord, helping you, the girl, lost and scared but with friends like you and Sam helping me through." Not Ruby of course, her lies still stung at the angel. For all Crowley was, he'd never been anything less than honest with her and she appreciated that more than she ever thought she could have.
"Its not just...that night and those feelings, even though it really did mean something to me at the time. It's everything I was. And I'm not that now, I'm losing that. It's being pulled away from me bit by bit and its a wrench in my soul every time I fall a little further. When I did it first, it was quick. I had no memory of being who I was, but when its not willing, its slow. Its painful. It's eternal. And you were one of the first people to look at me and see past the life I'd built for myself and I want someone to look at me like that again. So I want to give you the year back. I want my friend back."
She could never tell him about Crowley, any more than she could ever tell Castiel. They'd be so disgusted with her, they'd try to kill him. Neither was an outcome Anna wanted.
And yes, angels were weird. Yes, she was stalking his dreams because she knew it was the best and most undetectable way to do this. She needed to do it though, she had to.