(Takes place after Season five, spoilers for up to the end of that season!)
Anna was depressed. This wasn't a new emotion for her. She had felt it the last time she had been human. However, this time was definitely different. This time she actually knew why she felt that way, and this time, she knew she deserved to be unhappy. And it was all because of the Winchesters.
In short, she had betrayed them. Even after Sam and Dean had risked everything to help her keep her freedom and get her angelic powers back, she had had tried to kill their parents before they were born. Oh, she had good reasons, at least they seemed good at the time: She was going to stop the apocalypse and save the world. It didn't seem to matter at the time that she would have to erase a lover and a friend from existence in order to do that. But then...
Then she had been killed by the archangel Michael. Everyone else had thought that was the end of her story, but it wasn't. And that was the real tragedy.
It turned out angels didn't die the same way people did. When a human's body was destroyed, they went to heaven or hell. When an angel died(a rare occurrence) their soul had nowhere to go, since their heavenly form was destroyed, and their souls were still too pure for hell( although an exception had been made for the corrupt Lucifer. who had been caged). Therefore, angels who died became earthbound, taking on corporeal form and possessing fully grown human bodies, but usually no memories of what they had been or done. Many become homeless wanderers or were locked in mental institutions. Anna was different. She had been human before, and regained her celestial form for a time. Having made a similar transition once. she remembered everything, which only made things worse.
Oh, she knew how to survive as a human alright, but she was plagued with guilt over what she had done; especially after the apocalypse came and went. The world had been saved without the eradication of Sam and Dean from the timeline. In other words, the terrible actions that had made her a traitor and gotten her killed had been completely unnecessary!
Now Anna was once again earthbound; with few friends and no family to her name. She deserved neither. But the worst was yet to come for the fallen angel...
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