I loved him, and sometimes he loved me too
It has been affirmed that the Winchesters have died several times. Especially Dean who, courtesy to Gabriel, had died even more in Mystery Spot. What if, every time he died he went to Heaven?
What if an archangel was waiting for him, hopeful and bleeding from a torn bond of soul and grace each and every time?
What if Dean never remembered him? What if that was the reason Michael had become so cold and arrogantly rough? What if it was the only way he could bear his broken heart?
"What do you think my brother could do to me that he hasn't already?" Michael asked.
But it was more of the problem of what Dean - liberated, master torturer of Hell, forever bloodthirsty with the Mark of Cain painting his world in black - could do to him. Especially when he was rather determined to test whether Heavenly Swords were really made beyond breaking.
It follows the story of Tears in Heaven but could be read as a standalone too.