Just before he was impaled through the metal spike on the wall..

You had gone with Dean on a hunt, for a Vampire, Jenny and well.. You didn't do too much rather than be almost kidnapped before Dean killed all the Vampires but just in that moment.. He was about to be impaled by the metal spike you got in the way and it.. Impaled you.

It was trespassing your stomach while the blood loss started to do it's work. It hurt so bad, but, you and the Winchester's had gone in worse. He was worried, as hell! You were about to die and he was unable to stop it.. If he took you out of there you would already die in his hands. The uncontrollable tears that rolled down his cheeks as he held you by your shoulders were enough to make you question: Where you will go? Hell or heaven? Or maybe the purgatory..? That was something you didn't want to find out.

' It's okay.. It's alright I will just- take you to the Impala and we'll fix this.. I promised that you'll be fine so be it.. '

Dean held your shoulders tightly as he noticed how some tears started to roll down your cheeks.. You weren't supposed to die, and he knows that.. Only if he had his guard up and moved before that happened, he could have saved you. He blames himself for everything; Cass's death, and now yours.