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Did I just come back to scream into the void here? Yes.
My brain is broken and refused to sleep unless I spit this out. It's bad, but probably not as bad as the finale.
The nightmares started on the first night of their supposed freedom. Not that Dean wasn't all too familiar with nightmares as it was, but something about the black goo taking everything from him over and over again left him sweaty and breathless and sometimes screaming into the void of darkness surrounding his bed.
Some nights Sam would hear an echo of heartbreaking sobs through closed doors. Sometimes only breaking glass and muttered curses. When the nightmares kept his brother roaming empty halls through the night he'd slip out of bed, careful not to jostle Eileen awake, and pretend he just needed some water while he coaxed Dean into useless small talk. 
But Dean loved Sam's Eileen stories. Badass hunting trips and a quick getaway to somewhere sunnier than the bunker. The time she saved his ass from a vampire or when he officially asked her to move in to kick off the beginning of Men of Letters: New and Improved. Even through the exhaustion and the booze and the denial, Dean was happy for Sam. Absolutely thrilled that he picked up the pieces of his life Chuck left scattered all around their feet. And so quickly at that.
"I'm worried about Dean," Sam signs to Eileen during breakfast in the kitchen. He's slow, hands fumbling around, but he says it too. Whatever she can't get out of it she can read off his lips. "He can't live off of cheap liquor and regret forever. It's already been two weeks."
"And if I died right in front of you?" She asks. "Wouldn't you be pretty messed up?"
"Of course," he says too quickly. "We've lost Cas before," he stares into his egg white omelet for a long moment before looking back to Eileen, "but he always comes back. At least he used to."
"You're thinking more than you're saying."
"I just don't understand why Jack-"
"Took off on us like his ass was on fire," Dean interjects from the doorway.
Eileen turns to follow Sam's stunned gaze and finds Dean already looking at her. "Good morning."
"Morning, Eileen. Sam." Dean pours himself a cup of coffee and joins the table, daring Sam to continue. "So, what about Jack?"
Sam is about to say something about breakfast when Dean pulls out a flask and spikes his coffee. "Uh, I wonder what he's up to. Being God and all."
"Nothing. I think he made that pretty damn clear when he vanished into thin air. So why don't you worry more about your new hunters network, and less about whether Heaven really cares about any of our problems." 
"Right," Sam says defeated. "Do you want some bacon or something?"
"No." Dean leaves as abruptly as he entered, robe flowing out behind him.
"He'll pull through," Eileen reassures once shes pretty sure Dean is gone. "He's a Winchester afterall."
Sam manages a small smile at the thought of a Winchester being exceptional at handling emotional baggage.
Dean wakes violently from his slumped position at the library table, goodbye, Dean ringing in his ears. When he focuses his eyes he notices a sticky note on the nearest lamp and goes to retrieve it. His fingers brush just past, and the note flutters onto the tabletop. The letters carved into the wood are a slap in the face all over again as he reads Sam's explanation through blurry eyes. 
Ran to the store. Call if you need anything.
The one thing I want…
He doesn't know how the table ends up on its side or why, and Sam doesn't ask.
It's two in the morning when Sam startles awake. He hears yelling and immediately jumps into action. Only when he nears the site of the chaos, do the words start to sound more like English than a banshee. 
"Jack!" Dean yells at his bedroom ceiling. "Jaaack! Get down here right now and tell me why!"
"Dean," Sam interrupts. "What the hell."
The fight seems to drain from him with Sam breathing down his neck. "He owes us an explanation."
"You don't think I've tried praying to him?" Sam only half asks. "All the time. But he's not listening. And if he is... hes just not coming."
"Hello." The boys spin around to find Jack, hand raised in a casual greeting. "I know you're upset, but-"
"But nothing," Dean spits. "Where the hell have you been?"
"Heaven, mostly. But Hell, too."
"So you've been busy then," Sam says, too relieved to see the kid to be angry.
Dean looks between them, waiting for something to happen. Waiting for an answer to his prayers. He finally opens his mouth to speak, but Jack starts first.
"I can hear you, Dean, all the time. And I've missed you guys. But Heaven had to be repaired, and Rowena and I have sorted out Hell now, too."
"And?" Dean says expectantly.
"And I'm afraid I can't give you what you want," he says carefully. 
"What I want? I want a straight answer out of someone every once in a while. I want-"
"Castiel," Jack says matter of factly.
Sam hides his grin under a fake cough. The last thing he wants is to set Dean off again.
"So you're telling me that even with God power you can't yank an angel out of the empty? What happened to Chuck pulling Lucifer for his last stunt, huh?"
"Cas isn't in the empty," Jack acts surprised they didn't know. Like this isn't news.
"What?" Sam asks for a stunned Dean. "Where the hell is he then?"
"Heaven," Jack answers cheerfully. "He helped me… redecorate. I told him that Dean kept praying for him, but he seems hesitant."
"Why didn't you tell us that you got him out? Why didn't he tell me?" Dean lowers himself to his bed before he collapses.
"I thought you knew," Jack says sadly. "I would never leave Cas. He's my father. And he sacrificed his life for all of us. He deserves to be free."
"What the hell happened that day?" Sam asks.
"Cas's deal with the empty," Jack begins, and Dean doesn't have the heart to stop him, "was that he would be taken only when he experienced a moment of true happiness."
"True happiness? While running for his life with- AH. Oh. His happiness." Sam hears his own laughter before he realizes that its him. "Shit."
"You're gonna do that thing where you just shut the hell up," Dean says. 
"Anyway," Jack presses on, not catching the lack of need for detail, "Cas told Dean that he loves him. And that he couldn't have the one thing he wanted. Then the empty took him. But we patched that all up now."
"I see," Sam says, still grinning. "Dude, hes embarrassed. You gotta tell him."
"Tell him what?" Dean asks.
"That you love him," Jack answers.
"I don't- I can't just- what the hell is happening here?" 
"Well, Jack, we should go catch up before you take off."
"Okay. Dean-"
"Let's leave Dean for now. I think he has a few things to get off his chest."
"Oh. Right." Jack follows Sam out of Dean's room and gently shuts the door behind him.
"Cas," Dean squeezes his eyes shut and ignores the tears sliding down his cheeks, "you got your ears on?"
"Hello, Dean."
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all time low, coming back to their fans in 2020:
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