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In the end it wasn't Sam who said yes. It was Dean, and it happened before Detroit because an angel was dying and he couldn't let go.
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It was so depressing but it has a very happy ending at the very end
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https://archiveofourown.info/works/59825
A Deafening Distance by shirozoraSuppossedly angsty
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Dean says yes to Michael to save cas' life
Detroit destroyed