He wakes alone, disorientated and in a coffin.

That, probably, should have freaked him out more than it actually did but he had just woken up from 40 years in hell and there was not much left that could freak him out. Though, honestly, waking in his grave wasn't among his happiest memories and it might explain why he's now slightly claustrophobic. He doesn't think much when he crawls out of his grave, or more precisely he tries not to think too much, because he feels that were he to think about things right now his brain would explode. He doesn't know much either- actually he knows everything but he's trying to think without remembering hell which isn't that easy – just that he has to get to Sam or to Bobby. Which means first he must make it out of here. Later, much later – years later in fact when he accidently runs into the damn things again – he wonders what those books say about this moment. How did Chuck even begin to describe the pain, the disorientation and the fear? Were there even words to begin describing it? Was there even a way people who had not been to hell could understand? He'd been there, for longer than he cared to remember, and he didn't understand it so how could he even expect anyone else too?

(Maybe that is the real reason he hates those books and seriously dislikes those damn fans of Chuck's books. Because they think they know, they think they understand something they can't even begin too. )

He still doesn't know what Castiel said to him but he's not sure it matters.

He never asks him either.

He doesn't really think of Lisa until days later – after he's discovered that Castiel was an angel that had somehow, and he never fully understands how, saved him from hell. He still didn't fully understand why an angel had saved him nor did he believe he was really important but he did believe that Castiel believed this, which he supposes is just as important. When he finally does think of Lisa he imagines her in her beautiful home, in the garden sunning and drinking a refreshing drink while Ben played with his toys. It was the happiest scene he could think of and he imagined, for a moment, what it would be like to return to her, to be with them now that he was not dead. They would let him in their lives, they would love him but he's not sure that would be a good thing. He'd been in hell for 40 years after all, things had been done to him, and he had done things that were unexplainable and unacceptable especially for a good person like her. He was broken, beyond repair he thinks, and all he would do if he went to her was destroy her and Ben's live.

He could not do that to them.

Whoever uttered the phrase time heals all wounds was a complete idiot.

More than likely he had never actually been to hell – which was probable because if they had been to hell then they were now a demon and they would have better things to do than say things that don't really make sense. But whoever had said 'the show must go on' well that person was a genius, somewhat, and most than definitely right. There was no stopping time after all and the story wouldn't stop just because he couldn't deal – he was drowning in guilt and anger and memories of hell but the seals kept opening and the world kept turning even if he wanted to stop it. He'd learned this the hard way last year where he would have given anything for time to stop, even if it was just for a short time, but it never did.

Time went on, the story kept unfolding and now it included angels as well as demons.

And then there was, suddenly, a girl that could hear angels.

Anna Milton.

Pretty of course with long red hair and an easy smile and she'd looked so happy in that picture of her in her file. But when he saw her that first time, in the back of that church, she looked so sad and scared and alone and completely lost. He couldn't even begin to imagine what it would feel like to hear angels, constantly, but somehow it must be terrible (or maybe considering the fact she turned out to be an angel it was somehow comforting even if she didn't really understand it at that point.) And she looked at him – him who hadn't been able to stand the pain of hell, who'd said yes and tortured so many souls he'd actually lost count – as if he was her savior, strong and good, as if he, somehow, would (could) protect her. She barely glanced at Sam, though, for what it was worth, she did not seem to care that the angels didn't like him, but she kept looking at him for answers.

And he wanted to give them to her; he wanted to protect her from everything.

It wasn't an uncommon feeling, he'd felt it before, but it was somehow more powerful with her. Maybe because she was young and she'd lost everything, maybe because she could hear the angels and no matter what he said Dean actually trusted them, or maybe because she'd looked at him for answers even if he had none. She seemed nice and kind and he couldn't believe it, not at all, when Castiel said that they were there to kill her. She didn't understand it either – and he definitely didn't understand anything anymore especially not after she somehow managed to banish them – but she seemed so unafraid even though she must have been terrified.

But she still kept looking at him as if he had the answers.

Maybe he did and he just didn't know it.

Most likely however he didn't.

Bobby's house seemed like the logical, and really only place to go – and he has absolutely no idea why Cas doesn't guess they have gone there – and the panic room just the right place to hide Anna. Here's the truth he'd imagined almost everything could be the reason why the angels wanted to kill her – perhaps, he'd thought, it was just because she could hear them and that freaked them out especially if a demon got their hands on her and really he could understand if it was that and if it was he would have been able to talk them out of it by pointing out that just protecting her would be enough. The point is he'd imagined almost everything but what it actually turned out to be because her being an angel who had decided that becoming a human was the better idea – and really where the hell did she get that idea – well he'd never really considered that.

But it was what she turned out to be.

All they need is her grace, she says, and she seems incredibly reluctant to actually find it, like she doesn't want to be an angel again but she can just see no other way. Neither can he, for that matter, because if she stays the way she is she will end up in the demons clutches or she will be killed by the angels and he really, really doesn't want that to happen. He wants to protect her, to be the savior she clearly believed he was – and that was only, he knows, because she didn't know the full truth and if she, or Sam, were ever to discover it they would turn away from him just like he deserved – he wanted her to be that happy girl of that picture again. But of course she would never truly be again because that girl hadn't known about angels and demons and her parents had still lived and nothing he did would ever give her back the innocence she had lost.

But he still wanted to give it to her.

Even though her grace was no longer there he could somehow still feel it.

For the first time he woke in his grave he felt safe and at peace, even though he wasn't actually near her grace. Perhaps, most likely in fact, it was just his imagination, just his brain trying to give him some peace from his pain and memories. The tree was beautiful, more beautiful than anything else, but her grace was gone and somehow he knew that it was gone even before she said it, he suspects it was the look in her eyes. She looked torn, lost and for the first time he could see in her eyes that she didn't think he had the answers – which he never really had anyway.

Later, after she'd told him the angels were threatening to throw her back to hell, she'd looked guilty.

Like she wanted him to give her to them so he wouldn't have to go and here is the most horrible thing about him: he actually considered it. For just a second, when she'd spoken those words, his heart had practically stopped and he had been so scared that he had actually considered given her to them but then that moment was over and he realized he couldn't do that. No matter what it would cost him he couldn't just give Anna to the angels because he knew now that they would truly kill her and he knew why: because she'd dared to think for herself. (He still doesn't understand, despite her words, why exactly one would want to be human when one could be an angel, though after everything he's come to the conclusion that he wouldn't want to be an angel either.)

And then she'd told him she'd always known the truth and that she knew it wasn't his fault.

That he should stop blaming himself.

That he should forgive himself.

And even though he had heard other say it and he knew others would say it too and he knew Castiel had said it – though not in so many words – for the first time, a little part of him, actually considered she could be right. That perhaps there really was nothing he could do about it and he should try to forgive himself. And perhaps someday he would be able to but even though he'd listened to her and he'd believed her he still couldn't do it (perhaps with time she would have been able to truly convince him but time was the one thing they didn't have.) And then she'd kissed him and for truly the first time since hell he stopped thinking. And then Uriel had come to tell him to choose between his brother and Anna. And Uriel had known, of course he had, that there was no contest that he would always choose Sam (though, thankfully, he had somehow managed to miss their real plan which was probably good because otherwise it wouldn't have worked.)

But she doesn't know their plan either.

And even though she believes he's sold her out, that he's handed her over for her execution she still doesn't blame him, she still cares about him, she still kisses him goodbye because to her – and him – in that moment it's the most important one. And right before she stands before them ready to face her death she looks at him just the same way she did before: like he has all the answers, like he can help her, like he's her savior. (She never really stops; she always looks at him that way, no matter how much time passes. Even at the end, when she's suddenly different, she still looks at him like he can save her but like always he doesn't know how.) And then of course all hell breaks loose and they're all fighting and Alistair is going to kill them all and for a moment, just a second, he loses sight of her. Then her grace falls and shatters and light everywhere and just like that she's gone. And everything is different, everything is gone, because who she was and who she could have been and who they could have been is gone the moment the light hits. He knows that and she knows it too and he can feel it every time they interact after that.

He's sad but he's also happy because at least she's alive at the end.

Then she's gone and for the longest time he thinks she's truly dead this time but he doesn't dare ask Castiel because he doesn't want the angel to feel guilty. And then, in the middle of the apocalypse, she's suddenly back. She still looks the same – long red hair and beautiful eyes – but she's different, he can tell from their first interaction. It's her eyes really, they're haunted and sad and she's alone – more alone than she had been after her parents died – and she still looks to him for answers but she doesn't expect, not at all, that he can help her and she's right because he doesn't know what happened and thus he doesn't know how to change it.

And like before in a contest between her and his brother, his brother will always win.

She dies in the light, just like she was reborn in light, and he hates Michael and he likes him too. He wonders what it could have been like if he had met her in the world were they areboth normal, without the angels and the voices, perhaps they could have been happy. He wishes he could have helped her, saved her somehow and he genuinely mourns her even though he believes, honestly, that she died long before that moment, that she died when she was captured by the angels and somehow convinced – though he has no idea how and he thinks he doesn't really want to know – that this was the right path. She had died then he knows this. Because the Anna he met in that church, the Anna that had looked at him like he was a savior, the Anna that had loved him and forgiven him without a second's pause, the Anna that had faced her death with nothing but courage that Anna would never have considered doing this. And she would have been repulsed, angered, sad about whom she had become.

So he knows she died before that but it doesn't actually make him feel better.

He was so tired, he felt so alone and he knew that Famine was right, he was empty and he could not win.

Never.

Saying yes to Michael was the wrong thing to do, he knew this, it was the most terrible thing he could do. It would mean giving up on himself and his beliefs, on Cas who had lost everything for him and on his brother who was searching for redemption. But he was so tired – and he knew there was never going to be enough sleep in one lifetime to make him feel better – and the guilt was overpowering and he was alone and empty and there was nothing anybody could do to make him feel better. He knew what Sam would say and Cas and Bobby if they knew what he was thinking and he knew they would try to help him if they knew just how bad he felt but he doesn't really think there is anybody alive that could truly help him; he also knows how the angels would react but the way they think isn't the right way. This is also the reason why he tries to figh the feeling of giving in because he knows it's wrong.

But it's all too much, he's alone and he's done.

Paula said it after all: would it be so bad if the human's went to heaven, to their paradise? He would never be able to convince Cas and Sam of this, he knows this, and he's not just going to give in. If he says yes, and he's leaning towards it, than he's going to have Michael promise – swear, like Castiel swore to Jimmy before him- to protect some people. Lisa and Ben and Bobby and any friends he still has left and Sam (so long he said no) and Castiel (and there would be no deal without this one.) He would do this but first, first he needed to say goodbye to Lisa. Last time he saw her he'd been dying and he hadn't said goodbye but it felt like it and after he came back he never considered going back but now he has too.

He won't do it, this time, without saying goodbye.

So he sneaks away, to the world of the living, to her home – there where she'd lived years ago – but she's not there anymore. Luckily one of her old friends remembers him and she gives him the address of her new home – apparently Lisa had told her to do this if he ever did come back, like somehow she had known he someday would. She couldn't have of course, because back then he really couldn't have come back but she must have hoped for it. She's just as beautiful as he remembered her and just as kind. He has a million things he would like to say to her, a million things he wants to share but there is no time, not anymore, everything is lost now. Michael will protect her, because he won't say yes without his word, but after it is done he will never return here (because he knows, even though he's done fighting that it's the wrong thing to do and that in the end he won't be able to live with himself.)

But he still needs her to know it would have been her.

She wants him to stay, to say goodbye to Ben – but if he does he knows he's never going to be able to leave again – but he refuses. She's crying, he suspects he himself is too, and there are a million things he wants to say and he tries to think of something incredibly powerful that she'll remember forever but he can't think of anything. All he can think of is goodbye and he wants to kiss her but he can't, he settles instead for giving her a kiss on her cheek.

And then he leaves and he believes in that moment that that is the end of the story.

She doesn't come after him.

That's probably a good thing.