He had a life, before all this. He got away from Hunting, went to college, had a life, had a girlfriend. He loved her. This girl...by all accounts she was perfect. Everything he could have wanted.
Then Azazel...he decided Sam needed to get back in the game, Sam was important, from before he was born, and he needed to be a Hunter again, so Azazel took Jessica out of the game, he killed her.
I don't excuse it, I couldn't. But it was my in, y'know. Couldn't have done with I did if he had a cute little blonde wife, I'd never have known him and he'd have a normal life. He'd be a lawyer now, wife, kids, all that.
He loves me, I know. But I just, I can't stop thinking it should be her, that me even being in his life is messed up cause of who I worked for, who I still...
Azazel for all he did. He meant a lot to me Andrea, he was the first one to ever treat me like I was worth something, and sure, Sam says he brainwashed me, he was using me, whatever. Whatever it was. I was one of the few demons to actually be upset when Dean killed him. And I can't ever expect Sam to be okay with that since Azazel tore his life apart.
He loves me, but he'd love her too and it'd be easier, on him, on Dean...I can't ever be that.