The first time he sees her, after, is in his dreams. He's back in the vault, and even in his sleep he has enough peripheral awareness to curse his head for taking him there. It's a bad place, small and constraining and dark and it makes his skin crawl with the feeling of powerlessness, just like his childhood home did, just like the well. He can feel the dread mounting up and he knows it won't be long until he can't stand the quietness and the hopelessness of it any longer, and he knows exactly what will happen then. Some of his memories from that time are fuzzed, but the moment he stood up against the far wall and started to run at he opposite one will forever be clear. Somehow in his dream, he knows it won't take long.
And then she's there, on the other side of the electric fence, looking like she desperately wants something from him (he offered and she kept asking, kept coming, he wasn't crazy to think she truly wanted it, so why was she so angry that he gave it to her, in the end?). He realizes that her being there is his lifeline, and that he won't get another one. He can't tell if he feels that way because she is Skye, or simply because he needs to know that he's still wanted, still needed for something. He's been alone with his thought for far too long. And she smiles and thanks him for being honest about her father and then tells him it's time they got him out of the cage, and the relief is so, so great (it's a bad place, he might be calmer now but it takes all he has, every hour and every second, to keep it that way), he also smiles at her and feels his heart speed up with hope the first time in forever.
And the thing is, knows it's too good to be true. He knows he won't be forgiven. But he pretends that being useful can be the same. It has to be. If he survives (and he will not survive in here, he knows this for a cold hard fact) he'll have to be useful, be good, be everything she wants from him. It can work out, for both of them. He can do things for her that nobody else can. Things that nobody else will want to.
"You should change out of these prison clothes," she says, and sure enough there are his own clothes waiting for him on the neatly done bed. He turns around to get them, and someone fires. One, two, three, four... There is no pain, just the instinct to duck kicking in, except there is no cover to be had and the danger is behind him. There is a hostile behind him, and how on Earth did he allow that one to happen? Why didn't he see them? He turns around, instinctively searching for Skye. The shooter must be right behind, and how didn't he see...
"Never turn your back to the enemy," she says.
He jerks once more. It doesn't hurt that much, it's more the shock. Something starts ringing in his ears, and even without comprehending what is going on he feels himself cringing away, trying to fight the sensation of being left wide open. Unprotected. His heart runs wild, and he...
Wakes up. They're on a highjacked Hydra jet. Agent 33 is flying. Ward wonders at her name. He never met her while he was with SHIELD, and never asked while pretending to be Hydra. Their unlikely alliance is not as bad as it would seem. He can provide a good enough hideout - he has plenty of them, and she isn't operational right now and will not think to seek her own. Still, that is the extent of things he will be able to do for her. He can't help her figure things out. He can't help even himself, the fact that he's bleeding out of not even one by put several wounds is proof enough of that. He truly thought he could make everything at least a little better. He wasn't asking for forgiveness, or full trust back or anything like that. He only wanted to make her wish come true, and then maybe she'd know he wasn't evil incarnate.
He doesn't know why it went wrong. He also doesn't think he'll figure it out, this time. He already gave this plan for making up to her his best shot for months, and obviously it's been all wrong. He truly doesn't think he can come up with any better. Admitting that is a bad mental place to be. Everything - the cell, the well, his childhood home - everything bad ever leads him to this place. Where nothing he can do himself is right, and there is nobody else to help him. Where he is stuck, and can't tell left from right and doesn't know who he even is, and it's so much easier to simply end it.
The woman with May's face ignores the little moan he cannot swallow as he checks his wounds. They aren't bleeding too copiously for now. He forces himself to fall asleep again.
He gets to relieve the same dream once again, and then again, and then once more. Every time he closes his eyes, he's trapped back in the vault and Skye is there. Everything plays the same way, and he is powerless to stop it. He turns his back on her every time she tells him to, despite him knowing how it will end up, knowing she is the shooter (enemy), despite the pain. The bullets hurt now, and every iteration makes it hurt some more, but it's not the worst about this. Worse is the dread, the turning around even as he knows what's gonna happen. He doesn't want to, and still he does it. There are dozens of bullets in him now, and he has learned his lesson. She is the enemy. He gets it. He wants to tell her this, tell her that he knows better now and will never again presume to hope for anything from her. That he was wrong to do so. That he realizes that he'd screwed up, again, but he still doesn't know why. That he gave it his best shot, and that he's sorry his best was nowhere good enough.
A part of him is wondering if she'll go for the head shot if he confesses all this to her, and so he doesn't. The loop goes on and on, and by the time he wakes up the pain in his side is so much worse and there is a bonus of an ugly, nauseous feeling. He hopes it's the dream aftershocks, but being awake doesn't make any of it better. A couple of minutes more, and he's on his hands and knees in the back of the jet, throwing up dark coagulated blood and hoping not-May doesn't see. She might decide he isn't worth the hassle after all, not with the internal bleeding, and he really isn't up to being shot in the back again today.
He will be spared the necessity to admit that he lied to her, though, so there is that.