A.N.: Read a story on Archive of our Own called Saving People by Yalu, extremely great read and so awesome I would highly recommend. The premise being that Amara along with Chuck could give Dean a second chance to start over, Save Jessica, do everything differently and fix a lot of his big mistakes. I loved the idea and it got me going on what would be different…how I thought Dean would handle this but most importantly when I thought Dean would go. I mean it's a no brainer that everything sort of spiraled from Jess's death but would he really just decide to go back to only a few days before that shit went down? I always thought that Dean would be more inclined to think it started when Sam went to Stanford and that Dean would want that time to prepare. I mean imagine how much he could handle and get done in three years so that by the time Jess is even in danger; Dean had handled it so Sam could have the apple pie life. Which is what Dean wants for Sam. So here's my brain child. Inspired by Saving People by Yalu, the first chapter is very similar in origins but the rest will be completely different and my own brain child! Hope you enjoy!

"I guess darkness serves a purpose: to show us that there is redemption through chaos. I believe in that. I think that's the basis of Greek mythology." ~ Brendan Fraser

Chapter 1: We Begin at the End

"Dean, you gave me what I needed most. I wanna do the same for you." Amara said smiling. "What would make you happy? What would give you the peace you have given me?"

Dean stood staring at her for a moment, his first thought…his very first thought when he thought of peace was always his mother but it flittered away just as quickly. Even his mom couldn't bring him true peace, not after everything, not after Bobby, not after everyone he had failed one way or another. "Nah, we're good. The only way I could know peace would be to start everything…all of this over and that would only take your peace from you. I can't do that." Dean said with a sad little smile.

Then Amara got an odd look on her face and her eyes met with Chucks. "Not necessarily." She murmured.

Chuck looked a little reluctant but then he just shrugged at them knowing he would let Amara have her way.

"What do you mean the beginning? About starting over? If you could go back, what moment would you choose?" Amara asked stepping a little closer to him with every question.

Dean felt a little nervous and looked between the two gods before him. He thought for a moment…his first knee jerk reaction was to say when he went to get Sammy from Stanford but again after really considering it Dean realized it was another moment. The day after Sammy had left for Stanford, when their father had told him not to come back if he left and how he hadn't stood up to the old man. He had seriously considered leaving too because without Sam they weren't a family, just a soldier and his commander.

He had thought all that night about leaving while their dad went on a bender, and had tried to have the same courage Sam had when he had left. But in the end, Dean had stayed, because it was all he knew, all he could ever be, and he had always been so afraid of being alone. Everyone always knew that was where he was weakest…that he couldn't be alone. Now he wondered how everything would have turned out if he had left that next day, if had found that courage to tell his old man that no Sammy meant no him. What he could have learned about himself if he had taken that chance.

"The day after Sammy left for Stanford, I could have left too but I didn't. If I knew then, what I know now, I could have used that time…I could have saved so many more…I could have been so much more." Dean said staring with a small scowl at the ground.

Amara smiled, cupped his cheek and lifted his head up a little bit so he could meet her eyes. "You realize that if we send you back, it won't be like the other times? You'll wake up in your younger body, knowing everything you know now and you will be alone. Chuck and I, to do this will take a lot from us. I'll be back in the Mark, he will probably take a long nap and you will be alone. You won't be able to look to us for assistance, not for a few years at least."

Dean shifted and squared his jaw and nodded.

"You'll have to free me from the Mark again," Amara said mischievously.

Dean nodded seriously, "Of course."

Chuck groaned, "2001," he looked between the two of them, "really?"

Amara laughed, "Come now, it's the least we could do. The least you could do all things considered," Chuck shrugged and nodded.

Chuck grabbed Amara's hand and then she put her hand on Dean's head.

"When we turn back time, all of this will have never happened; you realize this means everyone you saved as well as everyone you lost will be back to where they started as well." Amara looked Dean in the eye seriously.

"If it means I get the chance to save Sammy from…to save everyone from…to save Cas…my family…all this heart break. I can do it," Dean of course didn't say that he saw this was a way to redeem himself from so many of his past mistakes. His mistakes with Sam, with Cas, with everything, it was his chance to do something in his life right for once. If that meant a whole lot of pain for him…well he certainly deserved that and more.

Chuck sighed, "Dean you are probably one of the most unpredictable beings I have ever created. You have a habit of ruining my most carefully laid plans and rising above every expectation I ever had for you. It's kind of annoying if I am honest but I want you to know I believe in you. If you say you want to go back, I am willing to swing that but I gotta say I'm surprised you haven't asked to bring Sam along for the ride yet."

Dean looked at the two of them hard, "If I am gonna be honest here, my first thought is to bring Sam and Cas back with me. But bringing them back won't fix what broke in them. I failed them so many times, failed to be there for them and they made so many of their own mistakes that will haunt them even if we fix it. I don't want that for them, I want to give Sammy a chance at having that apple pie life. If he came along for this ride he would never let himself get that. Cas…as much as I need Cas…I failed to be there for him every time he really needed me and he has been hurt in so many ways because of me. If he could forget this maybe he could find peace too, but not if he carries all this with him."

Chuck nodded, "Dean, you are always so quick to save your family, to bring them peace and happiness at the expense of your own."

"Their Happiness, their peace, that's mine. Seeing Sam grow old with a butt load of kids I can spoil and Cas all at peace for once…that's my bliss." Dean said in turn.

Amara smiled, "Like I said brother, you made something truly beautiful here. Now Dean, when you get back it'll be a little while before you adjust to your new younger body and well…being touched by us will certainly leave its mark on you. Try not to freak out."

"Mark? This isn't gonna be another Mark of Cain thing is it?" Dean asked nervously.

Chuck sighed, "No, but your soul has really been through the grinder Dean, Hell, Purgatory, Demon you, plus that soul bomb…well it's just not compatible with younger you. Your soul back then was whole and unscarred, weighed down with you insecurities and repressions sure. But it was clean and whole. Sending you back this way, to give you a real shot at changing everything you want to change…well we will need to adjust some things."

"Which means?" Dean said pulling out Sammy's Bitchface.

"For this to work I'm gonna have to make up the whole in your soul with grace." Chuck said.

"Wait, you wanna make me an angel? ME?" Dean said in disbelief.

"Kinda, not really but kinda. You wouldn't really be an angel because once you merge with your past self your soul will be healed. You'll have your own grace but you would also be human too…for the most part." Chuck mused and Amara grinned.

"So what you gonna give me a pair of wings or something?" Dean asked nervous as all hell.

"Nah that would kind of spoil that whole surprise element you are going for Dean. The only way this is gonna work is if the other players in the game don't realize you're playing too. As for your new grace…well I'm sure you'll figure out that on your own. I will say that I'll 'turn off' your soul so that no one will see how different you are going to be. It's gonna be on you what you change and the consequences of that. I have faith in you though Dean." Chuck said.

"Ready?" Amara asked.

"Oh and Dean don't forget you can pray. Pray to me, Pray to Amara, Pray to Castiel, just because you won't get a response doesn't mean we won't hear you. They'll be private as well, no one will be able to listen in on those I can do that much." Chuck said.

"Cas isn't going to know me though, wouldn't that put up all sorts of red flags?" Dean disagreed.

Chuck grinned, "Castiel has always been one of my more rebellious angels, he never really goes along with the plan and much like you he's intensely private. I doubt he would say anything, give it some thought and I'm sure you know not to say too much." He winked at Dean.

"Let's get this done," Amara said, "I'll be sleeping for a while but I never thought I'd voluntarily imprison myself for anyone ever again." She teased Dean and winked at him.

Dean felt guilty about it but he was too selfish to abandon this course now that he had been given this chance. He could do so much for everyone he loved; he could give Sam his shot with Jess, maybe even give Bobby a chance to be with Ellen again like in that messed up Titanic world. He could save them so much pain, his brother would never have to go to hell, Bobby could live a few more years and there were so many he would give a chance to…he had a shot at really doing something right for once in his life.

Chuck and Amara met his eyes as they placed their hands on his forehead. "This is gonna feel like you were run over by a truck while you were high on drugs Dean, try not to fall into denial over this because it would suck for this to be for nothing." Chuck said ominously before Dean felt it and everything went black.

~~~~~~~~2001~~~~~~~

When Dean woke up he felt like he had crawled out of Hell again and this time they hadn't fixed anything beforehand. He felt wrong in all sorts of uncomfortable ways and his head was spinning with everything. He spent most of the morning blowing chunks in the Toilet and cursing Chuck six ways from Sunday. Then after he had done that and was washing his face in the sink of whatever Chuck forsaken motel he was in he caught a glimpse of himself in the mirror.

The world tilted and Dean refused to admit he had been very close to full on chick flick fainting for about three minutes. As he looked at himself in the mirror Dean was in disbelief how young he looked, he was a freaking baby. It hit him then that this was real and he sat heavily on the bed then. Everything that had happened, all of it, the good, the bad, the ugly, all of it was gone and it left him feeling like he lost so much while also giving him so much hope. It was a sickening mix of emotions; he had the chance to make things so much better or so much worse. It was all on him.

Dean stared at the vomit colored carpeting of his cheap motel room for a while and just mourned it all. He mourned for Cas, for Sam, for Kevin and for everyone he had ever failed. He would change things, he would save them but Dean was beginning to realize the hurt of losing them…that would never really go away. After an hour of not moving Dean realized he needed to get going, he had so much to do and for some reason a little over three years seemed like not enough time. First thing he did was track down his cell phone, a brick of a Nokia, and track down the date.

A quick reminder on how to work the ancient thing and then the date is staring at him from the ugly small screen. It was exactly the day after Sammy left, which meant their dad was going to be on a bender for another two before Dean would have to see him. It would give him time to take stock of what he had weapon wise, what his money situation was, and give him a chance to photocopy their father's hunter journal before the old man knew it was missing. Dean had long suspected that their father had modified his journal when he left it for them the first time and he wanted to get the unedited version now.

Which meant he would need to break into their dad's motel room and then after he got his copy Dean knew he would be hitting up a tattoo parlor. He already felt exposed and naked from his lack of tattooed protection which was something he wanted to fix asap. He had a mission; a goal that he needed to focus his energy on and that would have to be enough for the moment. Dean didn't have the luxury of having a break down and that meant he had to get up right now.

He got up and took stock of his room. First thing he did was go through his duffle bag, salt, salt and more salt. His gun and a sawed off shotgun, a couple sliver knives. Dean was no longer sure how he had managed to live as long as he had the first time because this was ridiculous. He found a notepad and a pen quickly; there he drew out the protection tattoos he was going to need. Dean had been tempted to write a list of things he needed to get done but that would be the height of stupidity if the wrong person got a hold of it. He wanted the Bunker back, it was safe, it was the closest he had gotten to a home in the longest time and it hurt to have it so far out of his reach.

Then again, maybe it wasn't, inspiration stuck him like a bolt from the sky. The key Henry had couldn't have been the only one and he knew where to start looking for a spare…he would have to go visit the Wizard of OZ…well the good half of him anyway. However, he had things he needed to do first. He had to get his dad's journal, get his copy done, then return it and hit up a tattoo parlor. So that was exactly what Dean did after finding his wallet and the surprising flush of cash inside of it. Dean could vaguely recall that he had hustled some suckers at pool the night Sam left with the intention of giving it to him but things had spiraled and blown up before he could do it.

Breaking into their dad's room was unnerving, the man had been dead for almost a decade and Dean still wasn't used to the thought of having him hanging around. There had been a lot Dean had forgiven his father for over the years, just because it was useless to be angry at a dead man. Now, a lot of that anger was simmering in his gut like a lead weight and as happy as having his father be alive made him it also pissed him off. This was the man who hid so much from them, who had told him to kill Sammy if he couldn't save him…who had fucked up their childhoods so royally Dean had never had a healthy relationship with anyone his entire life.

A part of Dean still hated him.

Another part still loved him because he was his father.

Getting his copy of the journal and then putting his father's original back exactly as he found it was surprisingly easy. Then Dean stashed the copied pages with a mental note to get a binder for them and then he headed out to the tattoo parlor he had seen on his way back from the Kinko's. It was mid-morning and the place had barely opened when he got there which was lucky enough for him. He showed the heavily tattooed guy what he wanted and where then paid upfront for the work. The next five hours were spent under the needle with very little talking between them. The guy wasn't the talkative type and Dean was too distracted by his thoughts to put much effort into being his usual charming sarcastic self.

There was just so much he had to do and it would be so much easier if he could find another key to the bunker. Plus he was going to need money; it was 2001 so Dean tried to remember what he could of the next few years so he could so he could Biff the fuck out of it. Dean knew he was going to need some seed money because he definitely wanted to invest in the things he knew would get him a large return in the coming years. Plus he was going to have to do some international traveling, as sick as that made him feel (fuck flying), because there were certain things he needed to collect before they ever became a problem.

Dean decided that he would hit up the local library after this so he could use their computers. Tech sucked in the early 2000s and as much as he gloried of his Nokia's life battery he hated the damn thing. It was old and slow and only had so many minutes. Plus texting wasn't even a thing yet and that sucked. Sammy had been the only one with a laptop and Dean remembered it being as clunky and slow as his Nokia. When Dean had the frankly horrifying thought of dial up internet he panicked…when the fuck had that evil shit finally been put behind them? Was he gonna have to deal with Dial up now? Shit. He couldn't remember but with a sinking feeling Dean was pretty sure that was the case.

Well, there was very little Dean could do about it now but he had a vague thought of Frankensteining a laptop into something better and maybe he could try to hijack some broadband from somewhere. Those ideas were nebulous at best though and put to the back of his mind for now. Once he was done getting his artwork on his skin and listened to the aftercare instructions Dean headed straight for the library. Driving baby almost made him forget that he was in the past but the tiny things that their father had in baby at the time that denoted her as his made him slightly uncomfortable.

Baby wasn't his yet and Dean knew that when he confronted John Winchester about striking out on his own so soon after Sam had left it might mean walking away from Baby. He doubted his father would give her to him again not with him leaving so soon after Sam. His grip on the steering wheel tightened and he felt real panic at the thought of leaving her to their father. Dean pushed this from his mind when he got to the library and headed straight for the computers in the back. It was as he had feared, dail-up, on the other hand though the hacking tricks Charlie had shown him made it incredibly easy to do some pretty neat shit.

Getting into the funding of a few superpacks was so easy Dean almost felt bad about stealing from them, almost, the rich douche bags. He skimmed a few grand from here, a few more from there, nothing that would be missed but enough that he got his seed money as well as some cushion for the next few months. Next he looked for computer depots in the area and other places where he could get the parts he needed for his Franken laptop. Then it was a quick scan of the next few states over looking for a case he could hit up on his way to Clive's. Then he just cruised the internet for a bit to remind himself what was going on in 2001 and then he bounced.

Dean hit up a store with a money order place to pick up his stolen cash and cashed a couple of the money orders he had sent himself so he had funds for tomorrow. Then he hit a drive thru and got a burger and some pie before heading back to his motel room. Tomorrow he was going to get some more weapons and some other supplies. Then he was going to prepare himself for facing down his father. This was the one thing he had never done, he had never broken rank while his father had been alive…never been more than the obedient soldier and it was going to be very jarring for the both of them. Dean was sure that he could use Sammy leaving and the way his father had handled it as a rationale behind this big change.

All Dean knew for sure was that he had too much to do to put up with playing soldier boy to his father's commander and frankly he rankled at the thought of taking orders from the man ever again. He had been on his own for too long to fall back into the role he had once had as John Winchester's whipping boy and frankly Dean thought it would do him a world of good to confront his father on a small fraction of his fuck ups. Because the way he had handled Sammy leaving to better himself had been a major fuck up and Dean wasn't going to let anyone try to keep Sammy away from him.

After eating and showering Dean decided that it was time to do something he had been dreading a little since he had been back. He took out his Nokia and called Sam. Like the last time he had done this years ago, Sam didn't answer but this time instead of hanging up Dean left him a message. "Sammy, I get why you didn't answer but I want you to know I am proud of you. I understand why you're leaving, I get it, I do but I want you to know you always have me Sammy. You're my brother and we will always be family. If you need me call." Then he hung up and stared at his Nokia.

Sammy had gotten his full scholarship but that didn't mean he was going to have an easy ride. If things went the same way as last time Sammy would call him in about a week. Then they would talk once a week for almost a year and then Sam would meet Jess. That's when he would tell Dean to back off, that he needed to leave that life and him behind if he wanted to have a shot at normal. It had hurt so much the last time, because he hadn't known about Jess. Dean hadn't really understood why his Sammy had abandoned him until after all that shit went down. Sammy had been afraid that having Dean in his life would put Jess in danger and so when they had gotten serious Sam Ghosted him.

It had been a rough time in his life and this time around Dean was really going to be alone for the first time ever. No father, no brother and the thought of facing that made him break out in a cold sweat like it always did. He wasn't good at being alone, but Dean knew that this time would be so important to him. It wasn't just about the future, it was more than that, it would be a few years before anything major went down so for the first time in a long time he could have a chance to just be himself. There were only ghosts and monsters to worry about now. Barely any demon activity and angels wouldn't but there feathery dicks in until after the apocalypse was rolling.

That meant Dean had a pretty good grasp on how to handle things, monster and ghost were so easy. This meant he could finally be free to be and do whatever he was inclined to for the next few years. In between cases maybe he could finally learn how to play the guitar or the piano; maybe he could do a few comic cons or concerts. Maybe he could grab a little of normal life for himself, as selfish as that thought was, because right now he had the time. Sure he was gonna be training himself like never before, his body was nowhere near a level he was accustomed to and he was going to go after monsters with a fury that would surprise them.

More than anything Dean wanted to be better this time around, not only a better hunter but also a better person and that meant that he needed to discover who he was under all this shit. Maybe it was the fact that for the first time in years his soul was whole, he had the memories of hell but not the very real blight upon his soul. If he wanted to be a better person he had to better himself, he had to be patient, he had to be more open minded and understanding. Dean had to be stronger so that Sammy could rely on him more, could trust him more, and so he wasn't going to make the same mistakes.

The next morning he got up and hit up a weapons shop the moment they were open. He loaded up on a little bit of everything and then drove around until he found a store with hunter symbols. It was odd thinking about how little he had known back then, their community wasn't as isolated as his father had led them to believe and it was surprisingly easy to load up on the basics. After that he hit up a thrift store for some new clothes and some new cassette tapes. Everything he owned in this time had been from his father and Dean wanted something for himself. He bought a leather bomber jacket, some new threads and a blank journal for a hunter's guide that was purely his. It was time he started his own and he got a leather binder for his copied pages from his father's journal.

Before Dean realized it the next day and the confrontation between him and his father loomed before him. At his feet he had two duffle bags packed, his old familiar one and a new one that was full with his new armory and supplies. He was dressed and sitting on his motel bed waiting. If Dean remembered it right his father would come bursting into his room soon to tell him he found a new case and to pack his shit. He wouldn't mention Sam and he would shut down every time Dean tried to bring it up. That was fine, when his father came he would tell him the truth, he had another case and he was striking out on his own. That as long as Sammy was out of John's life so was Dean.

He spent the hours waiting for John working himself up, forcing himself to think of everything about John Winchester that had ever pissed him off and held onto that anger like a safety blanket. It was the anger he needed when facing down his father, he needed to be angry so he didn't break down from seeing him alive and whole. His father who had spent 100 years in hell for him, and had been dead for so long. There was so much left unsaid between them, so much hurt, so much anger, so much guilt, and he knew if he let it…it would fucking overwhelm him. What he needed was a shot of whiskey but he didn't move to get one…because he needed to be stone cold sober for this to leave no room for doubt.

Dean looked at his Nokia, the date burned up at him…it was Thursday. Maybe it was because he was afraid of what was going to happen…maybe it was because it was a Thursday…maybe it was that he felt so alone in this moment. For whatever the reason Dean bowed his head, clasped his hands, and prayed. "Hey Castiel, got your ears on? I don't pray, that's more Sammy's thing but I think I can pray to you. I don't know if I am going to be strong enough for this buddy, but I hope I am. Can I count on you to watch over me?" He said and smiled ironically. Cas, his Cas, was always offering to watch over him while he slept.

When John Winchester breezed into Dean's room he looked at his son all packed and said, "Good you packed your shit, I got us a hunt, we'll leave in ten." He made to leave but Dean stopped him with one sentence, "I'm not going with you."

John turned around with a scowl, "What?"

Dean didn't even bring up the fact that John was blatantly trying to avoid talking about Sam and replied, "I have a hunt, two states over, I just waited for you to show before I took off."

"Oh well if that's it then, we'll meet up after," John said expression clearing.

"No, we won't," Dean said watching his father's face get stormy again, "I'm striking out on my own, I am going to be hunting on my own for now. I get why you think Sam leaving is a betrayal, I get it, but there is no family without Sam and you know it. I don't get why you said the stupid shit you did, and until you fix that I think its best we not be around each other. Because, you see, I get why Sam left. He wanted out, he wanted that apple pie life and I am happy for him. You should be happy for him. This life, our life, it ends bloody. Whether it's at the end of a blade or the barrel of a gun I know how my story is gonna end. I'm not made for normal, you made sure of that, but Sammy is taking his shot and I am standing by that."

Dean got up and swung his duffle bags over his shoulders. John stood in front of him, his expression unreadable and stony. Dean nodded once and moved to head out the door. As he walked by his father John's hand shot out and grabbed his wrist. Their eyes connected and whatever John saw their in Dean's eyes made him back down. Instead of saying anything John simply pressed the keys to the Impala into Dean's hand and simply said, "Take care of her."

"I'll check in on you occasionally, make sure you're alive," was the last thing Dean said before he left his father there in that motel room.

Dean threw his bags into the trunk of his baby and got behind the wheel for the second first time as her new owner. He dug out a new tape he had picked up and threw it in the player as his baby roared to life under him. Back in Black began playing as he peeled off down the road; Dean nodded to the music as he gripped the steering wheel. This was just the first of the many changes Dean was going to do, the first, and for once it seemed like maybe he had a real shot at this.