Authors note: This is a work of fiction – obviously – and is intend to be taken as such. It’s just my thoughts on what Dean’s thoughts in season 8 might’ve been, if I could get into his head…
-sweetondean 

Entry 1

So I’m back. Topside. Land of the living. Benny was right, that son of a bitch. I’ll miss the bastard. Gotta be like this though... Good to see Sam alive and kickin’. Thank God. Was freakin’ out when he wasn’t picking up. Sam. Yeah. I’m trying hard not to… but damn it, unwritten Winchester rule, never give up on each other. Never. Guess he went on without me. Met some girl. Guess I should be happy about that? I dunno what to think. The Kevin thing, not cool. How could he leave him out there like that? I don’t get it. I don’t get the whole damn thing. We’ll find the kid and make it right, if he ain’t dead already, but Sammy seems…he’s not here or somethin’. Just tryin’ real hard not to be as mad as hell right now. Better try and sleep, in an actual bed. Things might seem clearer in the morning. Yeah right.

 
Man, nightmare. Monsters. Fighting. Same old, same old. Woke up sweating like a pig, no clue where I was. Then I hear Sammy breathing. Kid always was a noisy sleeper. Just gotta calm down. I’m back. Gotta remember, I’m back. I’m okay. It’s gonna be okay.


Well, found Kevin. Kid’s improved some. Turned into a good little fighter. Crowley’s still an S.O.B. Time we ganked that bastard once and for all. Turns out there's an actual tablet for demons. Tell's ya how to close Hell's gates. Could we catch that kind of break? Lock up the pit forever? Finally get rid of those black eyed sons of bitches. Man, that’d be somethin'. Sammy will back that. Yeah, Sam will be onboard for that…



Entry 2

I dunno know I even belong in this world no more. When did we blink over killing a bastard like Crowley? I don’t care whose meat suit he’s wearing. Kevin’s in the wind. Tablet’s gone. Sam’s got some bug up his ass about everything. Keeps drifting off, his heart’s not in it. I feel like the only one with his eye on the ball. Maybe it’s me. Maybe I’m the one with the problem. Nearly killed that dude in the interrogation room. So close. Gotta bring it down a notch. I’m on edge all the time. Everything was so much easy in Purgatory. Kill or be killed. No hesitations. Maybe I fit better there…Maybe I shoulda stayed put.


Christ. Nightmare again. Cass…


Entry 3

Great. Sam wants to quit the life and go back to college. That kid is full of surprises. Thinks I’d be better off hunting alone. What? Since when has either of us been better off alone. He’ll come ‘round. Just has to get back in the saddle. He won’t walk away. God damn it, Sam.


Entry 4

Let the werewolf chick walk. Couldn’t very well gank her and leave Benny breathing. Sam don’t know that though. Gotta say he looked a bit confused. Hey, maybe she can make a go of it? Not her fault she got turned into a monster. Maybe she can go against type. Not follow those instincts. Not kill anyone. Wonder how Benny’s doin’. Hope the bastard's ok. And I do not say awesome too much.




Entry 5

Yeah that went about as well as could be expected. Sam meet Benny. Super. Now he’s even more pissed at me than before. Yeah, I shoulda told Sam about Benny, I know it, but it’s not like we’re caring and sharing nowadays. Half the time we're at each other throats. He walked away, he wants out, thinks I’d be better alone… Hey and Sam, just to add insult to injury, meet my buddy Benny, the vampire. Heh. Oh well, he knows now. Let the shit storm begin.


One night, just one night’s sleep please without tossing and turning worrying about Sam or Benny or Cass or all damn three of them. Jesus.


Entry 6

Just when you think shit can’t get worse you get possessed by an evil dick of a spectre. Awesome. Now I’m spewing crap even I didn’t know I was still pissed at. Except that not looking for me thing. That hurts like hell and I’m trying not to...but I’d be lying if I didn’t say it’s gnawin’ on my insides. I know what Sam said, I know he said he was honouring some half-baked promise we made, but we don’t walk away. End of story. I keep expecting to wake up and be a brother down. I don’t even know why he’s here half the time. He sure don’t seem to wanna be anywhere near me. If it wasn’t for the whole locking up the pit, I’m sure Sam would’ve ditched by now. Ah well, guess I couldn’t blame him after tonight. He’s gotta know that’s not how I really feel, right? No one’s more important to me than him. Freakin’ fought for my life to get back here to him. Make sure he was ok. Look how that turned out. Everything’s screwed to hell again. Didn’t appreciate him threatening Benny either. God damn it. Garth looked good though. Was kinda nice to see the guy. Hugs and all. And he’s right, Sam’s all I got. I gotta try to let all this crap go. Gotta move past it. Son of a bitch got wise.


Entry 7

Cass is back. Thought I was going crazy. Then ‘poof’ the nerd angel returneth. Turns out I didn’t leave him behind. He stayed. What the hell. Sure didn’t seem like that in the moment. I felt him slip away. I couldn’t hold on. Turns out he didn’t want me to hold on. Don’t know whether to be happy to see him or slug him. Dragged him all through freakin’ Purgatory and he bails on me last minute. At this point, why am I even surprised. How’d Cass get back here anyway? Something’s not right. He just shows up? And he don’t remember how? I mean, it's great to see the guy, but I’ve been doing this long enough to know when something stinks. And now we’ve only got half a tablet. What’s a bet we got stiffed with the dud half. On the flip side, Sam’s still here. No sign of him checking out college brochures. And we've still got Kevin, nearly all of him anyways. I gotta put all this shit outta my head. Man, I just want to hunt. Is that too much to ask?


Entry 8

Freakin’ cartoon anvils. You live long enough, you see everything.




Entry 9

You know… they’re both alive and that was the plan.


Can’t sleep. He ain’t picking up the phone. Gotta go talk to him. He’s not gonna want to, but I need him to listen. If he’s gonna go, he’s gonna go. But not like this. I’m not leaving it like this, not after everything. I’m sorry Martin died, I am, but he brought it on himself. The crazy bastard shoulda left well enough alone. I’m not sorry Sam and Benny are alive. One of them would be dead for sure had I not... I’m not gonna apologise for making sure my brother and my friend don’t kill each other.


Had to stop for some caffeine. Almost at Kermit. Feel like crap. I’m so freakin' tired. I know I'm losing Sam. He's been only half here for a while. Gotta try and sort this out.


Entry 10

Sam’s here. Benny’s gone. I had to walk away from him. I just gotta believe he'll be ok. But if it’s Sam or Benny? If it's come to that? No contest. Haven’t told Sam yet. Good on him for not pushing it anymore. I appreciate the hell out of that after everything. Didn’t think about how that text would affect him. Just wanted him out of danger. In hindsight, maybe not the smartest move I’ve made. Had to give Sammy a choice. I’ve been hanging on too tight and it ain’t working for either one of us. Had to let him go if that’s what he wanted. He needed to make that call himself. He couldn’t go on like that. We couldn’t go on like that. We haven’t gone through everything we’ve gone through to wind up hating each other. I don’t know what’ll happen next. But for now, my brother's here and we’re focusing on the job.


Can’t sleep. Cass is playing on my mind. Something’s up. That whole coming back and not know how thing, that whole thing with Alfie. Something’s not right. We can’t trust him right now, not until Sam and me figure out what the hell is going on.


Screw it. Who needs sleep anyway. Car could always do with a wash.



Entry 11

Things I thought I’d never see: Sam all painted up charging across a field with a sword above his head. That was fun. We had actual fun. I feel ok for the first time in I don’t know how long. When was the last time the two of us laughed so hard? Felt like little kids again. Felt good. Probably shoulda told him he still had some paint on that ugly mug of his before I sent him into the Gas ‘n Sip for coffee. Oh well, the bruise on my arm will be worth it just to see his face. Great to see Charlie again. She’s grown on me. Good to talk to. Bit hard to talk to Sam when it’s about Sam. Times like that I miss the hell outta Bobby. Gonna have to come clean with Sammy that I may have said we’ll be at the next big whatever it’s called. We got a kingdom to defend! Ha!


Entry 12

Men of Letters. A grandfather we never knew. My head hurts. Add another dead Winchester to the list. Dad always talked about his father like he was some deadbeat that walked out on him and his mom. Guess now we know the truth. He didn’t walk out. He died saving us. I wish dad knew that. Wish we'd known that. What would’ve happened if Henry hadn’t left that night? We’d not be raised hunters? Would we even be born? Time travel, man. Screws with your melon. Guess Henry turned out to be okay after everything. Would’ve been good to get to know him some, learn from him. He seemed to know a trick or two. Sorry he had to go out like that… Dunno what I think about this whole legacy thing. Who would’ve thought Mom’s family was the brawn and dad’s was the brains. Think I saw Sam’s eyes light up. He’s always been a little geek. A giant geek. Heh. Good to see the kid look half happy. Things are definitely on an upswing in that department. Wonder if that hideout is still standing? Now that'd be interesting.


-To be continued