Title: Here We Go Again
Summary: Losing his brother to the trials in closing the Gates of Hell, has taken its toll on Dean Winchester. With nothing left to live for, a certain Prophet-slash-writer thought to be long dead, makes him an offer. Dean opens his eyes to the night he made Sam leave Stanford to find their dad, only this time, instead of waking his brother, Dean drives off into the night by himself. Years later...

Chapter 2

Dean looked up into the darkness and whatever he was about to say was gone. His heart sunk when he saw the abandoned house by the dark road, near the forest.

"One of the worst nights of my life." He remembered saying that a long time ago, somewhere up there in heaven as he and Sam trekked down the road, looking for a God that didn't care. "The night Sam ditched us for Stanford."

"This is one of the things that you could change, Dean." Chuck said somewhere to his right. "You were the number one person Sam didn't want to leave behind."

"Yeah, tell that to his face. He left anyway. And this night…" He turned around, arms outstretched, a forced smile on his lips, "This became one of his happiest memories. My own personal, living hell."

"But you could change it." Chuck said slowly, hands gesturing to the house where he could hear loud yelling and bottles being broken into shards. Dean flinched as he heard his own frightened voice trying to calm the remains of his family, to put them back together again. He remembered being scared out of his wits, terrified, because he could see that Sam was leaving them and there was no stopping him.

He remembered having that same choice once, back at Sonny's, the happiest two months of his life. But then he looked out of the window, saw Sam and gave it all up just like that.

He was an idiot to think that Sam would do the same for him.

"And how do you propose I change it?" Dean swallowed as the door opened with a loud bang and Sam was by the door, his face livid.

He heard his dad yell, "If you walk out that door, don't you ever come back!" He flinched as he remembered the same words coming from his mouth.

"Anyway you wish." Chuck answered him, as he watched entranced, when Sam hesitated, he was staring at someone. Who? "You could tell him who you are, someone from the future. Drink holy water and do stuff that will prove to him you're not lying. If there's anyone Sam will believe, it's you. You can tell him that if he left now and chose Stanford, hundreds of people will die, almost always the ones he loved."

And hundreds of people did die. Including Jess, Sarah, and who knows how many others. They saved several, however the death toll always beat the rescued ones. But-

Sam went out of the door, closing it with a bang. He had a duffel bag on his shoulder, the only things he brought with him. It seemed like they were invisible this time too, because the youngest Winchester didn't even look up. He went down the steps and passed by them.

Up close, he'd never seen Sam so young, so well. The last he saw of his brother, he was lying on a hospital bed, deathly still. He shuddered and unable to help himself, he followed.

"Sam." He said but his brother didn't hear him.

Behind him, Chuck asked as he followed, "Do you want me to make you visible?"

It was a temptation, to be seen and heard. He wanted to stop his brother, to hug him and tell him not to leave. "No." Dean said instead. "Keep me invisible, I might give him a heart attack." Chuck may have nodded but he didn't see.

Sam kept walking, but his pace was slowing down. His face was a mix of confusion and fear but there was underlying disbelief and joy that he finally got out.

"I'm sorry." Dean said when his brother finally stopped, as though trying to absorb what just happened. He pretended that Sam stopped because he sensed him. "You might think that this is it, that it's over, that you're finally out… but it's not. It's going to get harder and I'm sorry." He looked at his brother's unseeing eyes, "I'm sorry because I won't be able to protect you from what's about to come."

Sam began to laugh, there were tears in his eyes but relief echoed from him. It hurt Dean to see his brother so happy when he was away from them, but he understood. It hurt but he understood.

"You're a good kid and you don't deserve any of this." The oldest Winchester said, "That's why I won't take any of this from you. I won't- I won't change this part because for some fucked up reason this is one of your happiest memories and I'll let you have that." He remembered a dying Sam, a Sam who looked out of the window of the Impala and saw men his age with children. He remembered longing on his brother's face. "I'll let you have this."

He started to walk away but the he paused and turned to walk back, "But I just wanted you to know that it was still pretty goddamn selfish of you to leave me behind." He started honestly and once he started, it was hard to stop, his voice growing in volume. "To leave dad and me behind… I had to clean up his mess and put him back together again, you know? By myself. And it hurt because- because I knew he would have preferred you over me any day!"

Dean was walking away again but he came back. Maybe it was because his brother couldn't hear him and the only one who heard him was some lazy-ass writer or because his brother was still alive here and naïve about his pain or because he knew that his unheard words wouldn't hurt at all, that he continued to speak.

"I was always there for you." Dean walked up to his brother, looking at that exhilarant face. It's so weird to be taller than Sam for a change. "I gave up all that I could for you and for what? Just to be left behind like that? Didn't you think, even once, that I would have wanted an out too? That I wanted to go to college, meet a pretty girl, get married and all that apple pie life? I was in this life longer than you and I hated it more than anyone ever could! I had to learn how to shoot when I was four! While I watched as Dad tried to baby you until you were eight!" He raised a hand but then clenched it into a fist, pushing it against his forehead as though to keep the anger in.

"But goddamnit it Sam, I loved you and Dad, so I tried to be okay with it. I really did." The hunter said, "But you keep leaving me behind and it's not okay. It's not okay, man… It's not." He buried his face in his hands, "It's not."

There was a beat of silence as Sam tried to get his breath back, still blind to his grieving older brother in front of him.

"Dean…" Chuck said slowly. "If you're not gonna change this past, we should go." He added and Dean held his head up and exhaled.

"Yeah." He said as started to walk away, heading towards the prophet. A car came up from behind them and Sam excitedly waved his hands, signaling at it.

The hunter stopped beside Chuck and watched his brother hitchhike, getting in the car and talking with the driver. The car door slammed shut and Sam put on his earphones as the driver began to take his little brother away from his only family.

Dean closed his eyes as he remembered what happened next.

The door to the abandoned house opened, and he heard someone, himself, hurrying down the steps. He opened his eyes and watched himself stumble a few times, face terrified and hurt as he tried to run after the car taking his little brother from him.

"Sam!" The older of the Winchester siblings yelled as he raised his hands while he ran. The driver had probably turned up the music so he couldn't hear anything and Sam was busy with his goddamn earphones. "SAM!"

"No one will hear you, so shut your goddamn cakehole already!" Dean couldn't help but yell at himself. Chuck gave him a sad look, but his younger self didn't hear and just kept yelling as though his own distress would make Sam rethink his decision.

"SAM!" The younger Dean yelled, "SA-"

"Dean." Both Deans turned to find their dad by the door, his face red but firm. "Leave it, boy. Even if he comes back, he ain't welcome."

"You can't mean that, dad!" Dean argued, "It's Sam! He'll come back! I know it!"

"Keep telling yourself that." His dad said in a gruff tone as he went back in, probably to drink some more.

"He'll come back. He'll definitely come back." Dean told himself and he walked to the steps and sat down, bunching the jacket around him, to keep him warm. "I'll wait for you, Sammy and I'll give you a punch in the face if you keep me waiting long." He said to no one in particular.

The older Dean gave the teenage him a sad look before he said to Chuck, "Let's go." He began to walk.

The prophet ran after him, "What happened after that?"

The hunter scoffed, "Right, as if you don't know."

Chuck shook his head, "I don't get visions of everything."

Dean sighed as he looked back at his hopeful, more naïve version, "What do you think, Chuck? I waited. I waited well into the morning, didn't even get a blink of shut eye."

"And when you're Dad told you that it was time to leave?" Chuck asked softly.

"I fought tooth-and-nail to stay. Even when we were officially gone, I kept coming back. Maybe Sam just got lost or something, ya know? I kept calling his phone but Sam knew all my numbers." Dean's eyes hardened. "He never picked up." He exhaled at his cold hands. "It wasn't until I went to Stanford and saw his name on the list of students that I got the message." The oldest Winchester turned to the prophet. "He ain't coming back."

Instead of assuring him that no, maybe it's not what you think, Chuck just shook his head in reply. He knew Dean well enough not to say anything. "Let's head on to the next point." He raised his hand and Dean closed his eyes, wishing for a better version of the past.

Chuck snapped his fingers.

When Dean opened his eyes, the first thing he noticed was the Impala. The second thing he noticed was…

"Stanford," He sighed as he ran a hand through his hair. "Let me guess, the night I brought Sam back to all of this, right?"

"Another point in time you could change." Chuck said as he looked around shivering a bit as he pocketed his hands. "And I won't stop you, if you choose to."

The hunter leaned against the Impala, suddenly feeling weak. "Why?"

The writer gave him a look. Having written Dean for a long time, it was no doubt he already knew what he was asking with that one word. So he shrugged and said, "It's a reward."

The man laughed harshly, "Reward for what? For being the best screw up in the world? Oh, so hell wasn't enough?"

"Dean…" He said quietly, "You can change what's going to happen here. You can prevent the deaths of so many people…"

The hunter hit the top of his car with a loud 'bang' but Chuck barely flinched. "And how am I so sure that this won't backfire on me too, huh?" He yelled, "How can I trust that the future that will result in whatever bullshit I change, won't screw me over, Chuck?"

"But whatever result it may be, it's still better than what you had." The writer answered simply, "That's what you're thinking right? That's why you're still here, arguing about this with me rather than ganking me with a nearby sharp object or something." He said with a wave of his hand.

Dean looked at him in frustration before his expression dropped to exasperation. "Where did you get all this mojo anyway, Chuck? If you're even Chuck or just some psycho bitch pretending to be him."

"I am Chuck… or Carver Edlund or whatever." Chuck said, his stance loose and pliant like the lazy writer he knew from so long ago. "The Almighty-Prophet-of-the-Lord Chuck, you knew. The writer of the Supernatural books with an archangel on his shoulder, blegh."

Dean gave him a suspicious look, "Then did you have these powers all along, Almighty Prophet of the Lord? Are you some type of trickster Demigod?"

The prophet gave him a wry smile. "That's more like it, the old, suspicious-of-everyone Dean Winchester I know is back. You're having hope again which is why you're starting to care and ask me questions." He said with a wiggle of his finger. "But you're stalling Dean and I can't answer your questions anyway. It'd be best if I don't. All I ask is that you trust me and choose what to do now. Not only for you but for your brother and for the people you love."

Chuck gestured at Sam's dormitory where his younger self will be breaking in, in a few minutes. "Will you wake Sam in the middle of the night and convince him to go with you. Or will you stop yourself and go look for your dad on your own?"

For a moment, Dean looked like he wanted to argue. He wanted to prod and ask what would he be sacrificing this time if he really did change the past? But then he thought back to the fact that he had nothing left to sacrifice now. Nothing left to lose. It was either this or going back to that future where there was no Sam, no anybody… and his heart stuttered at the thought.

"And if I do choose to stop myself… Does that mean that I wouldn't exist? That the me who lived through Azazel, Lilith, Lucifer's rising, the goddamn apocalypse, the Leviathans, the demons, and the angels… The me who remembered all that would be gone?" Dean asked seriously and not in fear of being erased. "And what would the point of that be? Even if I decided not to come get Sammy, Azazel would come right after his ass anyway and try to rope him back in. Jess would still die, he'd still die, and I'd still give my soul to get him back. And we'd make those same goddamn choices that lead to the end of the world anyway! There's no happy ending. We'll still be going through the motions and the world will still be a hell-hole bent on making us miserable."

Chuck shook his head, "Not if you choose to give your memories to your past self."

The hunter froze, "What?"

"This is why I didn't want you changing the past when you were four. Your four-year-old self wouldn't be able to handle the things you know." The writer explained, "But the Dean Winchester of now, you've seen the darkness of this world and I think you can handle a few memories that would help you save the few people you love." Chuck met his eyes, "This is the compromise, Dean, the one upside. If you do stop yourself now, you can give him everything you know of what will happen so that you can ensure Sam's safety and everybody else's safety."

Dean gulped but nodded.

"But there are consequences and things you can't change and I know you won't like them." Chuck said uneasily as Dean's dumbfounded stare hardened into a glare. "A few people are meant to die, like your mom, it's a fixed point in time, and it can't be changed." He raised his hands when the hunter glowered, "I'm sorry but that's how it is."

The oldest Winchester sucked in a breath. Who are these people? Surely not his brother or his friends or his dad again, right? "Okay." He breathed out, "And?"

"And the next one is pretty obvious." The writer scratched at the back of his neck, "You can't tell anyone about what will happen or what you think is about to happen. You're pretty much on your own once you start changing things and I'm sorry for that." He sighed, "I say this is a reward but seeing as how you'll be alone in this from the get-go-"

"Me being alone means squat." The hunter said seriously. "Sure I'll bitch now and again and man, I might hate it because heck, I'm just human and it will be hard getting by on my own, knowing all these things other people don't know. But my past self knows what's important and I'm counting on that. It won't matter to me if after this I'm alone, crawling on my belly, dying in some goddamn place trying to kill some goddamn monster, because I'll live. I'll make sure I'll live with those bullshit scars so that I can protect Sammy and Bobby and everyone else. I can never ever live for myself, I've always lived for them. That's why no matter what the bad side is, I'm thankful. Because unlike some sorry jackasses out there, I get a second chance."

Chuck couldn't help a wry smile on his lips, "And this, Dean Winchester, is exactly the reason why you're called the 'righteous man'. You may think you're some useless pile of garbage to be thrown away, but you have a magnificent soul and I'm sorry that you can't stop hating yourself for one second and see that."

The hunter gave him a strange look, not knowing if he should accept that as a compliment or feel insulted, but then a familiar figure came skulking from a nearby vending machine and Dean abruptly turned.

It was his younger self, back when he was twenty-something. He looked so young and yet his eyes already held the dullness of seeing too much ugly in the world. In his hands he was nursing a can of root beer. He remembered drinking it all in one go and saying, "Let's do this!" trying to pump himself up before his inevitable meeting with his brother.

The same brother he gave up everything for but left him behind anyway.

As though hearing his thoughts, the young Dean tensed before opening the can of beer and drinking it all up.

"It's now or never, Dean. Just touch him and think about everything you've seen, that'll do the trick." Chuck said behind him and the oldest Winchester took a deep breath and nodded. The prophet tapped his shoulders and cold air rushed out of his skin, leaving it warm like something had been lifted from him.

His younger counterpart chose that moment to turn and he dropped the can he was holding, "The hell-" Dean strode forward with purpose, closing the distance in a few steps, grabbing the other by the shoulders in a strong, firm grip before he took out his gun. "The fuck are you-"

The tired, righteous man closed his eyes and allowed his memories free. He allowed every crap emotion, every unshed tear, every desperation, frustration, sadness, and hopelessness to color his every thought and memory. He felt the younger him freeze in his hands but he kept going and hoped whatever he was doing was working.

He tried to remember every moment, every regret, every 'could have been', every disappointment, every mistake, every heartbreak, and every sacrifice. He went into detail of what to avoid, and what not to do, of who not to trust, and of who to protect. He recalled every death with vivid color, his heart clamoring in his chest at the guilt. He remembered the deep, dark, nothing his soul had become after years and years of covering it up, of trying to be strong. Something wet and warm slid down his tired cheeks and he tried not to acknowledge it, thinking that maybe it was some rain warmed by his temperature or sweat from concentration.

Then eventually, he had to let go, falling into a kneel as his younger self fell with him, slumping in his arms. He felt the younger Dean tense at their position and he knew that they both remembered the same thing from his memories. Sam dying in his arms at Cold Oak.

"No, no, no… That won't happen again." Dean said as he cupped his younger self's face and forced frightened green eyes to look at him. His mouth was opening and closing as though not knowing what to say. The barely adult him seemed like he was on the verge of breaking down, eyes raw red and seeming about to cry from what he saw. Dean supported the back of his neck with his hand and patted his cheek like how he used to do to his little brother. "Don't you fucking break, you hear me? Don't you breakdown from this… You got a second chance and you're gonna man up and move on. It's the only way to save everyone."

His younger counterpart flinched at the word 'save' and the horror remained etched on his other's face. His eyes were looking sideways trying to process the images in his head. Still, the barely adult Dean swallowed and nodded.

"Good… good." Dean suddenly felt tired, his eyes were drooping and he wanted to lie down and sleep so bad. But he knew what was happening, he was fading. He smirked, Well, that was fast. At the back of his mind, the survivor in him panicked but in his heart he knew that that this was supposed to happen if it means that the future he came from was to change. So his arms fell to his side and this time, he was the one to slump forward into the shoulders and arms of his younger self.

"You protect them." He mumbled onto his dad's old leather jacket, one that he had long outgrown. "You do everything you can to protect them." Were this parting words? One last instruction to himself? Was it alright to tell himself to try to be happy for a change? Or was it more of a mercy to say to cut yourself off from every human being who could crush your heart just so you won't get hurt? Smaller hands grabbed at his tired arms. He let out a sigh and one last regret, knowing he would be heard, that this would be the last time he would be heard. "Protect them because in the end, I…I couldn't." Green eyes closed at the admission…

…And like a sudden exhale, the thirty-one year-old Dean who had lived through hell, the apocalypse, and so many wars… was gone, leaving his younger counterpart to take the burden in his place, kneeling, green eyes wide still with that unmistakable fear.

Chuck stepped forward, shaking his head. "Selfish prick. Didn't even say goodbye properly." But his face was tired and grieving as he met the eyes of a much younger Dean. "Heya, Dean."

"Chuck." The voice hadn't developed into that deep tone of the thirty-one-year-old Dean yet. There was uncertainty in his tone, like a person trying to place a name to a familiar object. "What the fuck is happening? Why did I- Who-?"

The prophet could already see the confusion forming in the eyes of the Dean that hadn't lived through any of the horrors yet. He sighed, the kid was going to have some nightmares for awhile.

"Long story, short, kid, you need to choose what you're about to do here." The writer explained, "The other Dean believed that you'd choose the right thing to make sure no one else dies in the future. After receiving his memories, I'm sure you know what he'd choose."

Dean looked at the dormitory he remembered breaking into several years back- no, that wasn't right, he hadn't broken in yet. It was the other Dean who did. His temple throbbed as he nodded slowly, "I'm- I'm not supposed to drag Sam into this mess again. I'm supposed to leave and not look back."

Of course, that's the route the older Dean would've chosen to take. "And?"

The barely adult Dean shakily got up, "I-" He stumbled a bit before straightening, squaring his shoulders. "He's right but- after what I saw, I- I have to watch over Sam and Jessica… M-Make sure Azazel doesn't fucking do anything or ruin anything but I-I have to get the Colt and-"

"One at a time, Dean." Chuck said as he raised his hands trying to pacify the hunter, "For now, why don't you get some rest?" He said as he extended two fingers to the other's forehead.

The hunter turned, green eyes misty from trying to remember. But through the haze of confusion and fear, suspicion broke through and he narrowed his eyes, "Chuck, who are you?"

The prophet paused and then smiled in amusement. The fact that Dean was questioning who he was proved that one way or another, the hunter would be alright. The writer shrugged his shoulders, "I already told you who I was before, but you tried to assure me I wasn't."

Well, there's only one explanation. Chuck said after he drank something to get rid of his hangover. He looked up seriously, Obviously, I'm a God.

Sam shook his head slightly, You're not a God.

As this certain memory was clamoring for attention in the younger Dean's brain, the prophet stepped up clamping a hand on his shoulder before turning and placing two fingers on the other's forehead.

"You're-" Dean managed to choke out before his eyes rolled back and he fell to the ground in a dead heap.

Chuck leaned down a sad smile on his face, "I told you God will make it up to you, one way or another." He reached out and touched the necklace around Dean's neck. The hunter was too out of it to realize that it was burning his skin.

"I'm sorry for being late, Dean."

The first thing Dean realized when he woke up, was that he was in the Impala, still parked outside of Sam's dormitory, and it was still nighttime. Second, he remembered the memories clamoring at the back of his head, memories that weren't supposed to be his in the first place but in one way or another was given to him. The third thing he realized was that no matter how hard he tried to remember, he couldn't make out the face and the name of the person who sent him here and why.

"Urgh, it feels like I chugged down gallons of beer and have the world's biggest hangover." He muttered to himself as he reached for the key in the ignition and started up the engine on his Baby. The engine purred to life and Dean smiled and patted the dashboard through his exhaustion. At least there was one constant in his life, the one thing that never left him.

And that was his beloved Impala.

As he was about to drive the hell out of there, he suddenly saw a figure coming out of the dormitory building, wearing a tacky jogging outfit.

It took everything in him to stay put and not call out.

Dean's heart squeezed in his chest when he made out the once familiar figure of his younger brother, Sam, putting on his earphones and doing warm-ups before his jog. He looked at his radio clock and realized it was four in the morning and that his brother had always been a salad-lover and exercise-freak.

It felt like something was lodged permanently into his throat and his eyes burned as he inhaled sharply through his nose. After having his short nap he was able to think more clearly now and he knew that Azazel wouldn't be going after his brother yet, so it was safe for him to be away for awhile and focus on looking for the Colt. Besides, from what he remembered, his dad would be sending some people asking for help and he had to be ready.

Dean's grip on the steering wheel tightened and just as he thought that maybe it wouldn't be so bad to say hello, a memory of Sam dying in his arms flashed in his mind. He bit his lip, trying not to scream at the pain in his head and in his chest at the thought.

I get it, I get it! He said to himself, I can't!

The throbbing eventually eased and the oldest Winchester panted and rubbed at his eyes. Only the dull ache in his chest remained and he forced himself to look forward easing his car out of the parking lot with gritted teeth.

He liked to think that he didn't look back in the rearview mirror when Sam started to do his running. He liked to pretend that he wouldn't miss that gigantor of a brother who used to look up and need him as much as he needed his little brother to be there.

And to ease the ache he felt at leaving behind a person who did not care about him, he fooled himself into hoping that maybe the reason why Sam stopped when he came out was because he caught a glimpse of the Impala and not because he had to stoop down and tie his shoelaces.

Author's notes: My heartbreaking headcanon: On the night Sam left, Dean waited for him for days to come back. He stayed up all night, hoping Sam would come back.

YES, Castiel will appear in the future, worry not! So will Adam :3

Thanks for tuning in this fic guys :D I appreciate the reviews (shame aside, PLEASE REVIEW) The next chapter will be years after this, how life has changed for everyone after Dean's choice. Next update is on Saturday. Thanks again!