You don't even get a depressing one-liner this time because that's how upset I am about writing this. 

Warnings: Spoilers for 13x22&23 and Sabriel :) 
(Comment and I'll tell you without spoilers, because there's important plot in this chapter)

Dean was frustrated to the point where he could slam his head into the wall repeatedly, just so his brain wouldn't be in a state to think. It was only 4 times this had happened, and yet it felt like it had been going on for years. Not only was someone showing him these horrid scenes, but they were also playing with his time perception. Either that, or he was sending himself insane. Both were likely.

Don't ruin the fun now, you've still only got one way to go; up.

That wretched voice had Dean tearing at his hair again. He so obviously knew the voice, yet his brain wouldn't be allowed to process it. As altered as the voice seemed to be, there was a familiarity that ran clear through the Winchester's head, taunting him with the fact that he should know, that it should be easy.

Screaming would only give him more of a headache, so he walked up the stared again. Dean just hoped that one of the times he reached the top and swung the door open, there'd be no one there and he could make the jump himself.

Today was not that day. But then again, he had no idea what days were in this strange-ass loop/

No, what the hunter could first see upon reaching daylight was gold.
Gold eyes were staring directly into his, looking tired. This was already different from the other encounters, as the figure didn't seem surprised by the intrusion. In fact...

"Hey, Dean-o."

Gabriel recognized him, looking almost as though he'd been expecting the hunter. The short archangel was leaning against the railing that everyone else seemed so eager to jump over, yet he was still facing Dean with his arms crossed.

"Gabe?"

The celestial being's lip twitched upward at the nickname. It was kinda nice, as not even his family had called him that in eons. The faint smile faltered upon remembering the situation, though.

"I'm sorry you have to go through this."

"What?" Dean was confused, as to why he seemed conscious to the effects of this fake world.

"I didn't know this is what he'd have in store for you. I didn't have any idea, and I'm sorry I couldn't help." Gabriel have a commiserative look to the hunter, spinning on his heal, regarding the open city below him. "I've never understood why people wanted to die. Being dead sucks."

Dean gaped. "So, you're actually..."

"Dead, stabbed by Michael himself from the other world, yes. Being forced into your brain like this, it sparked the smallest amount of grace to actually bring me here. I must say, your mind's a dark place, but it's better than the Empty."

It's your fault, Winchester, for getting him involved.

The archangel flinched, proving he could hear the voice as well. However, he shook his head. "Ignore him."

Dean was gaping again. He couldn't help it; He hadn't noticed how much Gabriel had changed until now, seeing him gaze over the railing with a sense of tired peace. This wasn't the Trickster they had known, who was willing to kill to show a point, or strictly for the irony if it. This was Gabriel, the broken archangel.

The said being finally broke the silence, saying, "When you get Sam back, tell him he was always my favorite." When receiving a confused, yet pained look, he only chuckled. "What do you expect me to believe? You two can never stay dead for long."

Dean finally cracked a smile, though the sorrow didn't stray from his eyes. "Right," he started, before playing Gabe's words through his head again. "Wait, what do you mean, 'he's your favorite'?"

"He was nice. Even knowing what I really was, and the kind of things I did. Sure, he's tried to kill me, but who hasn't?" Gabriel chuckled sourly. It was rather obvious how much self hatred there was behind his cocky attitude. He was beginning to remind Dean of himself. 

"You talk about him as if you're a teenage girl with a crush."

Dean was only teasing, but the look he got for it caught him of guard. "Do you?" He carefully asked. Pissing off an archangel, especially the only other one who was consciously there, was a bad idea. As much as he used to hate him as the Trickster, Dean knew better than not to trust him now.

"Dunno. Angels aren't supposed to feel anything, so when they do, it's... it's confusing." 
"Do you really think Sam can be saved?" The hunter changed the subject, seeing how tense the air had become. 

"Of course. I'd make sure of it myself." Hopeful silence passed before Gabriel started speaking again. "Cassie can be too, I can still feel his grace." 

Before Dean could ask how, the celestial being doubled over, appearing to be in pain as he fall back from the railing. Grimacing, he looked to meet the hunter's eye, who had crouched down before him.

"Guess he doesn't like me talking too much," Gabriel grinned rather pitifully. Dean looked like we was going in interject again, but again, wasn't given the chance to. "Don't do anything too stupid, you've got my grace inside you." 

Not knowing what else to do, and not particularly wanting to see Gabe die again, Dean pulled into a hug with his eyes screwed shut. "Ok Gabe, we'll get our brothers back. I'll see you again when we get out of this."

And only seconds later did he stumble into real darkness again, the sun no longer bright against his eyelids. He had only barley registered the words "You got that right" before he was tossed back, and strangely found himself more calm than he had any other time. Dean could only guess that was from the grace that supposedly was stored within him. 

He must admit, he could barely register the fact that the grace was there, and he thanked Chuck, wherever he may be, that it wasn't like dealing with Michael all over again. Tranquil thoughts were quelled when that stupid voice echoed through the hall, and Dean noticed for the first time that it wasn't in his head.

Restoring Gabriel in the way that I did was not intended. However, do not get too overjoyed with that minor screw up, you've got work to do.

As irritated as the hunter was with the voice, he ascended the stairs. The only way to get back to Sam and Cas would be to deal with this until there was another solution. He owed this, not only to himself now, but Gabriel as well.