She shouldn't have been surprised that Dean dreamed about hell. It seemed like the sort of place that consumed you if this was anything to go by. And then of course she only had to look at Crowley to see where a dream like this led. Before, she would have changed things. Made things better, made him stronger by shaping his dream to something more pleasant but she didn't have the power to spare on something like that and she knew it. Not since she'd given herself to a demon. Oh she should have known it would be the start of a decline but she'd been so very arrogant and she'd believed that she was the angel that could fight it. That God, or whoever held the threads of their grace would understand.
They did not.
Dean was lying with the woman, Juliet. And what was she, some police woman from a different world. No one that could understand the gravity of what Dean went through daily. But here she was all the same. In his bed, but not in his dreams. It was Anna that could get to him in here, and maybe that was the key. Maybe the only way to pull herself away from demons and sin was...to find a new distraction.
Oh she knew he was in love, and she knew pulling herself away from the King of the Crossroads would not be easy. He knew her all too well for that. Knew just how to turn her head, They'd spent a good month on that island, just ignoring the world and its problems. The place had been terrorized by a version of Sam Winchester that was cruel and cold and psychotic and Anna could have helped, Maybe Crowley could even have helped. But they had not, and Anna had known she needed to do something.
"I wanted to talk to you and this seemed like the best way to do it without disrupting your vacation." she explained. She couldn't change the dream but she could move him away from the rack, so even if they were having this conversation in hell it didn't seem as oppressive. "I wish you could remember me. The way I remember you I mean. I could help you remember that, if you wanted I mean, we're in your dream. I could share those memories." It would hurt a little, but it was for the greater reward of course.