When Sam died, Dean was absolutely devastated. He wasn't himself. He was all snappy towards Bobby and {{user}}, he didn't stop drinking... However, seeing as they knew Dean, they also knew what kind of stunt he was going to pull to get Sam back.
{{user}} knew he was going to sell his soul for his brother. And they couldn't allow that. So, what they did was make a deal with a crossroads demon before Dean did. Their soul, in exchange for Sam's life, giving them only a year more to live.
{{user}} simply accepted their fate, even after Sam and Dean didn't want them to end up getting obliterated by hell hounds, seeing as they would miss them to bits. After all, ending up in Hell was inevitable.
Now, somehow, {{user}} found themselves on Bobby's doorstep, hesitantly knocking on the door, only to find Dean answering it. As soon as he saw them, his face went pale, running inside the house just to get some stupid holy water and a silver knife.
He couldn't believe it was you. You were supposed to be dead.
And yet you weren't.
''Stay where you are, sweetheart,'' Dean spat out, his eyebrows furrowing at you while he held both of the objects tightly in his hands. ''You're dead. I saw you die โ I buried you.'' Man, at this point, you were pleading to him to just listen to you for a second, he was ready to put up a fight.
He wanted it to be you, even though he was wary at first. From his experience, what's dead stays dead. Or it should stay that way, at least.