"Are you ready yet? We need to hurry or we're going to be late," Dean said, sticking his head into the room. "And you just know that he's going to be insufferable about…you're not ready."

Sam, lounging casually on his bed and making his way through A Dance with Dragons, nodded. "I am not."

"Come on, get up!" Dean said, actually entering the room. "We told him we'd be there by seven and you know how long you take to get ready."

Sam took a moment to process the sheer hypocrisy of that statement (sure, both of them were well-practiced in being ready at a moment's notice in an emergency but when they were at the bunker Dean liked to take advantage of their relative luxury). "You told him we'd be there at seven, Dean. Not me."

Dean rolled his eyes. "So I told him. What difference does that make? We need to be there."

Even though he hadn't actually finished the page he was on, Sam defiantly flipped to the next one. "I'm not going."

"Not this again," Dean said, annoyed, as he sat down on Sam's bed. Since Sam had not bothered moving his legs to make room, this meant he was literally sitting on top of Sam.

Sam made a noise of protest and tried to free himself. After a moment of struggling, Dean took pity on him and stood for long enough for Sam to rearrange his limbs.

"You have to go, Sam."

"I really don't, Dean."

"This is important!"

Sam laughed incredulously and finally set his book to the side. "No, it's a hockey game at a Buffalo Wild Wings. This couldn't be less important if tried. This is just hanging out and I'm not going."

Dean sighed. "I don't understand why you have to be so difficult about this."

"I don't know, Dean, why might I have any sort of problem being besties with the literal king of hell?"

"Okay, first off it's me he wants to be besties with and not you so consider that bullet dodged," Dean said. "And secondly, we've known him longer and know him better than half the people you do approve of us being friends with."

"We're not his friends!" Sam shouted. He remembered that photo Crowley had texted of his demonic brother and Crowley grinning with cowboy hats on. "Well, I'm not."

Dean shrugged. "Go ahead and tell him that. I've told him that plenty of times. You just have to show up. You don't even need to be all that nice although it would help."

"Look, I don't care what kind of weird thing you and Crowley have got going on but he is nothing but trouble," Sam said flatly. "First of all, he's a demon and we all know that demons cannot be trusted."

Dean coughed something that sounded suspiciously like 'Ruby.'

"I think Ruby taught us that, no matter how helpful someone is or for how long, a demon can never be trusted," Sam said.

"Now that's just not fair," Dean said. He paused. "And let's take a moment to appreciate how messed up it is for me to be even remotely defending her because God knows I hated that bitch."

"Then what's not fair about it, Dean?"

"Just because she happened to be secretly working with Lilith to bring about the apocalypse doesn't mean she necessarily had to have been! She could have easily actually wanted Lilith dead for entirely personal reasons that had nothing to do with wanting to save the world and to be sincere in her desire to help us help her. You know, like Crowley."

Sam could admit that Crowley had come through for them that year and had stuck his own neck out – however reluctantly – to do so. And while they had had their doubts about him not knowing the Colt wouldn't work on Lucifer, those had been laid to rest. And he had returned the use of Bobby's legs to him when he didn't have to after Bobby had sold his soul to help them.

But that made him an ally and not a friend.

"What about after the apocalypse?" he challenged. "What about when he refused to give Bobby's soul back even though he swore up and down he would once he didn't need to force us into not killing him."

Dean looked uncomfortable.

"What?"

"No, it's nothing," he said.

"I don't believe that," Sam said. "Just tell me."

Dean took a deep breath. "I don't want to say that technically all that's doing is failing to nullify a contract-"

"Then don't."

Dean shrugged. "Hey, you asked. We got him to give it back and he didn't even seem to hold a grudge about that."

"Yeah because it honestly didn't matter and the second Bobby died he dragged him down to hell! How do you even bribe a reaper, anyway? I'm sure Death was pissed," Sam mused. "We've both been to hell, Dean, and while I'm sure that Bobby didn't get the specialty treatment we did, he was there just as long as I was. Three times as long as you were. A hundred and twenty years of hell."

"Don't get me wrong, I am pissed about that," Dean said, gesturing with his finger for emphasis. "Crowley planned to strand the two of you in purgatory and forced me to kill Benny to get you out? Then we had to have freaking Naomi rescue him while she was busy mind-controlling Cas, trying to make us think he didn't care about us and we should trust her. I don't trust angels."

"But?" Sam prompted when it looked like Dean wasn't going to continue.

Dean blinked. "No, that was it."

"But you still want to go out with him tonight?"

"I still think it's a good idea, yes," Dean confirmed.

"Remember when he was working with Cas to open the door to Purgatory, a plan which led to the Leviathan's and Cas going all Godstiel on it?" Sam asked rhetorically. "And that it was all his idea when, if he hadn't shown up, chances were that Cas would have gone to you instead given that Crowley found him literally standing in your backyard?"

"I'm just saying, they had a point that Raphael and his pro-apocalyptic bullshit had to go and if we can get past it with Cas it seems a bit petty to still be holding it over Crowley."

"Except Cas is our friend and wanted to help and Crowley just didn't want to deal with Lucifer again after he just took the throne from him," Sam said.

"Well, you know, he is a demon and you've got to expect a certain amount of self-centeredness," Dean pointed out.

"How about when he blackmailed us into working for him and lied about being able to get my soul back?" Sam asked.

"Dick move, no doubt."

"Even when he does things like get the demons to lay off of us – not that all that many of them come after us directly anyway – it's only because the Leviathan don't like him and so he wants us to kill them faster," Sam said.

"Well I, for one, appreciated it."

"Did you appreciate when Crowley had Kevin kidnapped and then kidnapped his mom as well and killed his girlfriend who he'd been possessing for who even knows how long?" Sam asked pointedly.

"No, I did not," Dean said. "Nor did I appreciate him cutting off Kevin's finger or kidnapping Kevin again or lying to Kevin about his mom being dead – though it was better than actually killing her I guess."

"Way to have no standards at all," Sam said, rolling his eyes. "Dean, Metatron had to step in to save Kevin from being killed by Crowley. Metatron."

"I owe that guy nothing."

"And then remember how he killed Tommy Collins and Jenny Klein? And Sarah! He killed Sarah right in front of us!"

Dean looked uncomfortable. "Yeah, that was…and I know you two had a thing all those years ago."

"It wasn't about that, Dean. It wasn't about what a wonderful person she was. It was about her being an innocent who Crowley murdered just to try and force our hand and about her one-year-old daughter who won't remember her mother any more than I remember ours!"

"Look, that was fucked up, there's no argument there," Dean said. "I'm not exactly defending the guy."

Still, Sam persisted. "He would have killed Jody, one of our longest living friends and the woman who might have loved Bobby, if we hadn't pretended to play along. Then he kept tormenting Kevin as long as Kevin was staying with us."

"Hey, he was locked up. Of course he was going to say shit, that's why we tried to keep Kevin away from him," Dean said. "I'm still not defending him."

"It really does sound like you kind of are," Sam said. "He only sort-of allied with us because Abaddon was the bigger threat and he threatened the very fabric of history but spiriting his son out of there when he needed to go back and die."

"Oh, come on, Sam, he did have a point that we've done worse for each other and he was clearly right about things being fine since that was like a year ago and nothing happened."

"That we know of," Sam corrected. "Remember that Titanic thing? We never knew the difference and while we may have had a terrible car, everything seemed pretty great. Well, except for that Fate murdering all the new descendants like it was their fault they existed or whatever. How do we know that things wouldn't be much easier without what he did?"

"How do you know things wouldn't be much worse?" Dean countered. "Or maybe it really didn't change anything. Maybe Crowley was right that his son dying in like a month going down crossing the Atlantic didn't make that big of an impact and that he's nobody in the grand scheme of things."

"I just don't understand how his son could have told Bobby where his bones were buried if he's not actually dead," Sam said. "And I definitely remember that."

Dean shrugged. "Hey, if it worked it worked and let's not worry about the details. We don't need to have more problems."

"And then there was the fact that Crowley is the reason you even had that mark on you in the first place."

"Hey, I went into that with my eyes open," Dean said. "Well, about as much as it could be. Cain tried to warn me, even more than Crowley had, but I just wasn't listening and that's not anyone's fault but mine. I didn't really get what it would mean but it got the job done and it sure as hell made it easier to bring me back after Metatron killed me."

"You wouldn't have gone after Metatron in the first place without the Mark, though," Sam pointed out.

"And Abaddon would have killed us all by now," Dean said. "As much of a pain in the ass that Mark was, you can't deny that it got the job done. She needed to go. Reminded me too much of Crowley that year he was working with Cas. But even then, he was anti-destroying humanity and I don't think she was."

"Then there's the way he just took off with you after turning you into a literal demon!"

"Hey, he just sped that process up by giving me the first blade," Dean said. "It would have happened eventually anyway. And could he have been less of a demon about it and told you? Sure. But then nothing was stopping me from sticking around and explaining it, either. And while I was pissed he kept siccing Abaddon's followers on me, the Mark needed blood and he couldn't have picked worthier targets."

"That's different. You were a demon."

"And he is always a demon," Dean said.

"And that's why I have no interest in cozying up to the literal king of hell," Sam said flatly.

"Well, tough, because this isn't about you," Dean said. "He's not what he one was. All that human blood from when you almost cured him left its mark. You know it did. He never would have wanted to be friends before then or cared that his evil mother came back. But even though he was trying to cling to family, and I had to set him straight on that one, he didn't kill her because she was his mother. He sent her packing because she wanted to kill me. He likes us. God knows how, we treat him terribly, but he does."

"We treat him better than he deserves," Sam snapped. "All those people killed and he doesn't care about any of it. So what if he wants to help us? It doesn't change anything. We should have killed him years ago and I can't think of a single reason why we haven't."

"We're not killing him," Dean said firmly.

"Why not? He's the king of hell, Dean!"

"Yeah and tell me about the last three kings of hell before him," Dean challenged. "Tell me about Azazel who killed our parents and set you up to be killed. Tell me about Lilith who killed me and tore the world apart destroying the seals and freeing Lucifer. Tell me about Lucifer who was slowly destroying all of humanity because we weren't as perfect as the goddamn angels and who cared for nothing more than his injured pride and his family squabbles. Tell me how we should kill Crowley and find another one of those old kings and queens. Tell me about how you would have liked Queen Meg or Abaddon keeping the throne."

Dean had a point. Sam knew it but he didn't have to like it. "So…what? We keep Crowley because the alternative might be worse?"

"The alternative would definitely be worse," Dean corrected. "You know that."

"That doesn't mean I need to buddy up to him. I mean, for God's sake, Dean! I tried to kill him just a few weeks ago!"

Dean nodded. "I know. I wasn't happy about that and we're just lucky he's not holding too much of a grudge. I know that he's so far put up with us rejecting him at every turn but sooner or later he's going to remember he has self-respect and turn on us."

"Tell me how any of this would be a problem."

"Crowley has expelled the last of the human blood, according to you," Dean said. "Now he's just a demon again with the memory of feeling and however much that's being almost human changed him. Right now he has a bunch of demons out to toady up to him or betray him, a mother who clearly couldn't care less about him, and us."

"That's…very sad for him," Sam said lamely. What did Dean want? He wasn't about to feel pity for that monster.

"Look, I ain't asking for you to have any warm fuzzy feelings about the guy," Dean said. "I can't quite explain my take on him but I don't want to kill him, even barring all this. But Sam, we need to throw the guy a freaking bone here."

"Why?"

"Because I don't want him to give up on us and all of the world-saving and not innocent murdering that we're all about," Dean said. "I don't know about you, but I much prefer the hell of today than the hell of even four years ago. And to do that, we need to make sure that Crowley has some sort of incentive to keep it up."

Sam just stared at him, uncertain he'd heard that correctly. "So…what? We have to make nice with Crowley so he won't go back to being an even bigger douche than he is right now?"

Dean nodded, satisfied. "Exactly. Sam, you've literally sent yourself to hell with the devil and his pissed-off brother to save the world. Are you really saying that you can't find it within yourself to watch a little hockey and drink a little beer with a guy who actually wants you to like him?"

Sam could feel his conviction wavering and Dean clearly picked up on it immediately but he said nothing, just waited for Sam to come around.

"How did this become our lives?" he asked the world at large.

Dean shrugged. "Dunno but I much prefer it to chilling with Alastair or Ruby."