Dean frowned down at the bottle in his hand, swirling it in a small circle and hearing the liquid inside swish around gently. The sound was almost soothing, to be honest. Almost. His recent argument with Sam had sent him over the edge - Everything hurt. The eldest Winchester brother just didn't understand how Sam could even stand to look at Jack. And it wasn't 'cause - 'cause Jack "got Cas killed", or that Jack's father killed Cas, or that he was Satan's son. Dean couldn't give two shakes of a rats ass...

That was right, wasn't it? Whatever.

...Whether Jack was the son of the Devil. He'd faced worse. He'd killed worse. Jack being the "antichrist", or so he said, didn't phase him a bit. No.

And he didn't care that, yeah maybe Castiel had died protecting Jack.

Mary had died trying to protect Sam. Did that make her death Sam's fault?

No!

"But I can hardly look at the kid. Because when I do all I see is everybody we've lost!"

And when he said that, he meant it. He really, truly, meant it.

Dean couldn't look at him, because everything - everything - about the kid reminded him of Castiel.

His face.

His smile.

His voice.

The way he squinted when he didn't understand something.

The way he copied Dean, followed him around like a puppy.

The way he dressed, for God's sake. And Dean couldn't take it. Couldn't take looking at a miniature of his best friend when his best friend was dead. Couldn't look at him because he'd just end up carin' for the damn kid. Start lookin' at him like a little brother, or worse, like a son. And then what? He loses Jack, too? Why's he gotta lose everyone? Why's everyone gotta leave? Why's life so freakin' unfair?

Dean closed his eyes and brought the bottle to his lips, tilting his head back and tilting the beer up. The liquid hit his tongue but it wasn't instant relief like usual. If anything, drinking made him feel worse. Why the heck was drinking making him feel worse? Shit. Dean didn't stop to breathe, swallowing one mouthful of beer after the other until the whole bottle was empty. Sighing, he sent it rolling across the floor toward the others, before reaching for an unopened one. He'd barely gotten the thing open when the door creaked open. Sam.

Or, he thought. He was too surprised when he saw Jack carefully step through the doorway and stand there. His gaze traveled around hesitantly. And while at first Dean thought maybe it was wariness there - Didn' know whether to feel proud or upset 'bout that - When Jack's gaze rested on him, all huddled in the corner drowning his sorrows in alcohol, he saw it.

Not pity.

But not sympathy.

Fuckin' understanding.

Dean wanted to throw the bottle at the kid's head and tell him to get the hell out of his room but another part of him wanted to talk to him. Wanted to get to know him. Wanted-

No.

Jack carefully came forward, hovering near Dean's bed for a few seconds before taking a hesitant step toward the hunter. Now he looked wary, but not for the reasons Dean thought. "Hello, Dean,"

And Dean wanted to laugh and cry at the same time because Jesus Christ this kid reminded him of Cas too much. And it hurt. It hurt. But beyond the pain he felt.. Almost, almost amused.

Almost.

"Sam asleep?" Dean mumbled, mentally cursing himself for how raw his voice sounded. Like he'd been crying. Which he most certainly had not been, obviously. Jack seemed confused by this question, giving him that look.

"Uh, no. Researching." Jack took a few more steps forward and settled down on the floor just a few feet away from the Winchester, crossing his legs like how Dean was sitting. Dean didn't bother readjusting his own position, pretty certain that Jack would do the same as well.

Besides, part of him liked it. Just a little.

"Oh." Was all Dean said, lifting the bottle back up and taking another sip. This one didn't last as long but he managed to down at least half the bottle.

"I came to check on you," Jack spoke slowly, choosing his words rather carefully. Still, didn't stop Dean from rolling his eyes at him.

"Don' need checkin' on."

"I know. You just seemed very.. Upset, earlier." Jack rushed to explain, but his voice was still slow and careful.

Like how Castiel used to talk to him.

Dean took in a deep breath, his gaze trailing away from the nephilim. He had to stop. He had to stop comparing every little thing about Jack to Castiel. Because Jack wasn't Castiel. He maybe looked like him and talked like him and dressed like him and acted like him but he wasn't him.

"Mm," Dean sighed, then tipped one of the unopened beers over onto it's side and rolled it toward Jack with two fingers. It hit the kid's leg, and Jack stared at it before slowly picking it up.

And he gave that stupid, stupid smile like he'd accomplished something, like he'd gotten some reward. Because that little gesture had pretty much said everything Dean couldn't. Well, wouldn't.

You can stay if you want. Maybe I don't hate you as much as I say.

But he'd never say that. Not yet. Not till he had things figured out. Truth was though, Dean couldn't hate Jack. He couldn't. It was like hating Cas.

A miniature, more powerful, Satan's-son Cas but still like hating Cas. Dean couldn't hate him. And he couldn't hate him because Castiel had absolutely adored this kid.

So how the hell was he supposed to hate him?

"I know you... Miss Castiel." Jack spoke up again. Dean's gaze slowly moved back toward him, eyebrows pinching together. Jack frowned at him. "And your mother."

And Dean wanted to laugh again 'cause Mary hadn't crossed his mind for a while. Okay, that made him feel bad. But if he was being honest with himself, he knew Mary was dead. She'd pissed Satan off. You don't piss Satan off and not get killed. 'Course, Sammy's gotten by on that one before, but that's only 'cause Lucifer needs him. Used to need him, 'least.

And also because of that painfully obvious schoolgirl-crush he had on Sam but that wasn't the point right now-

"I do." Dean replied honestly, narrowing his eyes slightly at the kid across from him. But the look must not have been hostile - And Dean wasn't quite sure if he intended it to be - Because Jack simply nodded and smiled hesitantly.

"I.. Miss Castiel, too," Jack murmured. "And my mother.." He trailed off. "Did you know my mother?"

"Briefly." Dean wasn't sure why the hell he was talking to Jack at this point. But he wanted someone to talk to.

Even if that someone had to be his dead best friend's doppelganger.

"She was.. Good," Jack paused, looking down at the beer in his hand, which he still hadn't opened yet. "Was Castiel good?"

Dean felt that lump rise in his throat, the annoying thing trying to push tears out of his eyes. He blinked them back and looked away again. "He was the best."

"But I'm not good." Jack murmured. "Sam.. Wants me to be good."

And Dean didn't say anything, didn't want to, because if he opened his stupid mouth he was just gonna admit he wanted Jack to be good, too.

So he didn't. He kept it shut and nodded.

"I'm sorry."

Two simple words, but it was the most emotion Dean had heard from Jack. Honestly. the kid's voice was strained, shaking slightly. Dean's head rolled around so his gaze could fix on the nephilim, his first instinct being to reassure him, tell him it was alright. Because that's what he'd say to Cas.

But this wasn't Cas. And he couldn't say that now.

Still... "Sorry for what?"

"For..." Jack's voice shook harder, trailing off. "For being the reason Castiel died."

Dammit, this kid... Dean took a deep breath. He was so going to regret saying this, but Jack was so close to tears and Dean was drunk and..

"Lucifer killed Castiel... Not you."

The hunter watched several emotions flash across Jack's face. Confusion, disbelief, pain, fear, disbelief again, then confusion. "I don't... Understand.."

Dean's lips twitched slightly, fighting the mask he had in place. Maybe Jack was more Cas's kid than Lucifer's. "Cas dying..." He paused, struggling to word this. "Lucifer's the one who killed him, Jack. And yeah, maybe.. Maybe Cas died 'cause, 'cause he was tryin' to keep Lucifer from you," He gestured a hand vaguely at nothing in particular. "But that... Was his decision. Not yours. And it was Lucifer's decision to kill him... Not yours."

"So.." Jack struggled to think of what this might mean now. "You don't... Hate me..?"

"I don't hate you." Dean allowed, narrowing his eyes at him. "But that doesn't mean I completely like you."

Still, Jack smiled, and Dean fought with everything he had to keep a straight face.

"Do you think I can be good?"

The question was unexpected. Dean didn't really know what to say to that. The truth, or lie? Truth, or lie? Truth, or..

"I think," Dean sighed, tearing his gaze away from the nephilim. "I think..."

Truth, or lie..

"We've all got... A little angel, and a little devil on our shoulders.."

Truth or lie...

"And ultimately, it's up to us which one we wanna listen to. The angel tryin' to steer us down the right path or the devil tryin' to lead us down the wrong one.."

Truth...?

"But I think if you care enough to wanna be good.."

Maybe...

"And if you care enough to wanna try and see that light at the end of the tunnel, care enough to listen to the angel, care enough to try to take the right path..."

Truth.

"Then you're already halfway down it." Dean sighed, turning his head around to look at Jack. "You've got a chance."

He was surprised, so surprised to see tears shining in the kid's eyes. Jack blinked them back, staring at Dean for a very, very long time. He expected this kind of talk from Sam but not Dean.

And Dean... Dean would blame it on the alcohol in the morning. He might actually pretend to not remember this in the morning. But he would. He'd remember every second, every word. And so would Jack.

After all, this was Dean's way of saying he was giving Jack a chance. That was good enough for him.

But if this conversation got brought up ever again after this night Dean was either gonna deny it or blame it on the beer.

Jack was okay with that.