You meet

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Dean-

You were on the same case as the Winchesters and decided to help out.  While on the hunt, the demon kidnapped you and tortured you, wanting you to tell her where the amulet was.  You, obviously, refused, and she carried on with the torture.  Dean crashed through the door, attacking the demon.  After he cut you loose, he carried you to the car and prayed to Cas and had him heal you.

Sam-

You were at Truman High, and you, Barry, and Sam were best friends.  It broke your heart when Sam left, and your heart broke even more when Barry committed suicide.  After ten long, depressing years of hunting, you ran into Sam and Dean again, and, this time, it was for good.

Castiel-

You came back from a hunt with the Winchester's, disappointed that you couldn't save that poor little boy from the vamps.

"Y/N," Dean started.  "It wasn't your fault."

"You couldn't have saved that boy," Sam continued.

You appreciated that your best friends were trying to reassure you, but it wasn't going to work. 

You walked into the bathroom and stood in front of the mirror.  All you saw was a person who was too weak, too dumb, too fragile to be a hunter.  You continued to stare into the mirror for  a little while longer until, without hesitation, you drove your first into the mirror.  You fell to the floor sobbing until you felt strong arms wrapping around you, then you were sitting on one of the motel beds.

You looked up and saw his ocean blue eyes, giving you a worried look, then he healed your wounds.  That's when you knew...  You met an angel.  You met Castiel.

A/N:  I know Sam and Dean's were a lot shorter than Castiel's.  I hope you enjoyed this first preference.

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