It's a Sorry Excuse for a Goodbye.
Dean watched Tessa close her eyes, and prepared for the worst. He thought she'd being taking him on... to wherever he was supposed to go next.
But that's not what happened.
The whiteness of that nonexistent room he'd created in his mind faded away, and Dean stood in the real-time hospital room his brain had based it on. He stood, staring blankly at an all too familiar figure on the gurney. Suddenly he remembered the flash of something he'd seen when he first woke up, that nagging image he'd seen in a flash and forgotten in a split second - it was this. It was the real world, trying to break through.
The something on the bed that he'd seen but not comprehended was himself, laying on a white sheet tucked over a slightly inclined gurney, a riot of tubes coming and going out of his body like desperate chaos, and the steadily beeping machine that told him he was alive, but couldn't deny he was close to dead.
Dean watched his little brother try not to cry at his bedside. The look of his own broken body lying there, so obviously empty of him, was haunting. Sam brought a hand up to cover his face as he tried but failed to keep the tears in. "We've always gotten through this before. You've always pulled through..." Sam tried to protest. "Dean, I don't think..." he faltered, and it was heartbreaking. "I don't know what to do, man. I'm sorry..." He laid a hand on his brother's body, resting it on his chest, and Dean brought his hand to his own ghostly chest, as if hoping to feel Sam's touch transferred there.
Suddenly there was a crushing guilt - he was leaving his little brother to fend for himself in the big, cruel world after all. For Sam, even more than for himself, Dean suddenly wanted more desperately than ever to stay.
Tessa felt it.
Suddenly they were somewhere else. Dean glanced around, confused - it was a claustrophobically small space, mostly inhabited by shelves. But it didn't take him long to realize why they were there. Somewhere in the Hospital, in a dingy broom closet full of paper towel rolls and bottles of cleaner, Bobby Singer was sobbing into his shirtsleeve, desperately trying to keep silent, his face red and pained and wet from tears. He was getting it all out before he went back to be strong for Sam.
Dean had never seen Bobby cry - he doubted if anyone ever had. It ripped a hole in his soul to see the man so heartbroken. He regretted asking Tessa to show him this. In a selfish kind of way it was almost nice to see that he'd meant to much to the man, but really, Dean had never doubted it. And now he'd seen how his utter stupidity and useless heroics had hurt Bobby more deeply than Dean could ever forgive himself for, and he knew the sight would haunt him forever.
He turned to Tessa, not meeting her eyes. But it was enough of an indication for her to put her hand on his shoulder and take him away from this room.
Up on the roof of the Hospital, Castiel was staring out at the crack-of-dawn-lit city. His face was blank, his eyes leaking silent tears down his face.
Dean tried to keep his voice even, "What'll happen to him?"
Tessa considered the question for a moment. Dean knew what she offered was as much as an educated guess, a prediction based on seemingly unlimited information, and Dean took it for what it was worth. "When his fellow Angels come calling again, Castiel will return to Heaven. No longer having a reason to stay on Earth." Dean winced at the ache of knowing he could have been that reason. "He will return to his former duties, leaving the world of man and its grief mostly behind him. He will check in on Sam every now and again. Other than that, he will become very much the way he was before he met you."
Dean didn't know if there was anything sadder. He stepped forward, coming up right beside Castiel and wanted so much to touch him.
He'll be alone, Dean thought sadly.
"He'll have his brothers," Tessa tried to comfort.
Dean reached up to Castiel's cheek, wanting to brush his fingertips against it. But he couldn't. He walked up as close to Castiel as he could, he leaned in, a breath away, and he whispered, "I love you, Cas. I'm so sorry I never said it."
Cas' eyes closed, and Dean told himself that somehow, Cas had heard.
Dean closed his eyes too, staying close, pretending he could touch him. And in that moment, the closeness was almost enough to imagine he'd held him.
He never wanted to leave Cas' side, but Dean was not one to drag things out. He breathed deep and pulled himself together before he turned back to Tessa. "Alright," he started in a brave voice. He smirked at her in that all too Dean Winchester kind of way, "Let's do this."
She extended her hand to him, smirking fondly despite herself, and after a moment he took it.