Dean sat next to Lucifer at the hotel's bar, grateful that all the effort to restore the building hadn't vanished when the pagans fled. He poured himself a glass of tequila and took a swig before looking across the room to where Sam, Gabriel, and Castiel sat, giving him and Lucifer a small amount of privacy. He understood that Castiel and there others were still wary of Lucifer, but he could do without the armed guard.

'You appear to be healing well, Seraphiel,' Lucifer said softly. He lightly brushed his wings against Dean's.

Dean stretched one of his wings out and shrugged. 'Yeah. It's been a process,' he admitted. 'How are you doing? You don't look so hot.'

In answer, Lucifer made an attempt at caressing his Grace. Dean sighed heavily and allowed a small piece of himself available. The sudden flood of desperate love almost had him opening up more, but he resisted. Barely.

'This vessel is deteriorating, but I can maintain it for a while longer. But that is not what bothers me. Being surrounded by demons…' Lucifer broke off with a huff. 'I must admit, I'm tempted to not help you and just let the world burn.' He lifted a coaster and examined the stylized depiction of a grinning devil.

'I know humans can be pretty shitty, but I'm sure torturing and encouraging them to torture others isn't exactly helping them,' Dean bitterly replied. 'Speaking from experience, of course.'

Lucifer turned his head to stare at Dean. 'You should never have been put in that position,' he said as he caught a brief flash of memory of Dean being cut into.

Dean tried to shrug off the sorrow that filtered through to his Grace. 'No one should be put in that position,' he insisted. 'Wasn't Hell supposed to be for reform and contemplation? I thought the torture was supposed to be reliving your shitty acts from multiple perspectives. I get things changed, but I thought everyone was exaggerating about the whole torture shtick until I woke up on the rack myself. What the fuck happened?'

Lucifer stared into the distance, regret spilling over through their connection. 'The first demons I made before Michael threw me in the Cage… Those facsimiles of our brothers and sisters. I let my resentment and hatred infect them. It only got worse over time. I never… This is all my fault. Do you think humanity would have improved without demons walking the Earth?'

'Hard to say,' Dean reluctantly said. 'Some humans don't need a demon to get them to start a war or murder someone. They're perfectly capable of it all by themselves.' He shrugged as he sent out waves of regret. 'Sometimes…an angel can get them to be assholes, too. And sometimes they prove you wrong and resist temptation and manipulation.' He let out a soft laugh and shook his head. 'Used to fucking piss me off so much when I came across a truly virtuous soul. I'd like to think I finally got over that,' he mumbled as he finished his drink and refilled it.

Lucifer's Grace continued its slow caresses, and he greedily drank up every bit of love and understanding Dean sent his way. Even if Seraphiel's Grace was corrupted, he still shone brightly with love. It made Lucifer ashamed that even if his Grace was comparatively pure and untouched, he was capable of so much hatred. 'You're healing, but you are still tainted.'

'Yeah, thanks for the reminder,' Dean grumbled, sending a ripple of spikiness along his Grace. Along with a big 'fuck you' to drive the point home.

'I mean that you are purified, but your experiences still shape you. You still comprehend their struggle.' Lucifer's Grace lightly probed what he was allowed, skimming along the surface memories of Dean's experiences with humans. 'Good and bad, righteous and evil… You understand them in a way none of us could ever hope to.'

Dean tapped his nails along his glass. 'You were all up in my Grace before...before. Was I always this fucked up?' he asked. Anxiety spiked as Lucifer remained silent. He was afraid of the answer. The confirmation.

'You were different,' Lucifer eventually replied, sending a reassuring stroke of love. 'You experience love differently. Looking back, I should have learned from you.'

'Too late now.'

'Perhaps not.' He threw Dean a small smirk. 'Death offered to help remove a Bobby Singer's influence from Sam Winchester.'

Dean stiffened as his breath caught. 'Yeah, and? What're we gonna be up against? He's not gonna just off him, right?'

'No. I kindly rejected his offer. I will not need his help to move forward with the apocalypse and gain Sam's willingness.'

Swallowing, Dean threw a quick glance to Sam and tried to dig deeper into Lucifer's Grace for answers. When he found none, he replied, 'You seem pretty sure about that.'

'Am I? Or did I buy you the time you so desperately need? I'm sure you can feel the restlessness. Everyone is growing impatient,' Lucifer said. His Grace flitted along Dean's, allowing amusement to filter between them over Dean's exasperation. 'Death seems to be fond of a place called The Pizza Corner in Chicago.'

'Wait. Seriously?' Dean said incredulously.

'You've suffered enough for my choices. This is the least I can do.'

Dean snorted and propped his arms atop the bar. 'Since you're doling out favors... I've got this friend,' he began.

'The demon, Crowley,' Lucifer said with a knowing smile. 'Such a strange fondness you feel for him.'

Dean let out the breath he was holding. 'Yeah. Could you, maybe, call off the dogs? I mean, he's a dick, and he probably deserves it, but…uh… He's… I dunno. My drinking buddy? He pisses me off, but I still like him, okay?' he finished, defensively crossing his arms. 'He…he was the closest thing I had to a friend for a while.'

'I never called for his death,' Lucifer replied. 'I suggest you keep him hidden if he means enough for you to seek my help. If I were to ask for the hunt for disloyalists to end, it would bring suspicion. I already told them it was a non-issue. Come the end, it won't matter.' He picked up Dean's discarded glass and sniffed before taking a sip. He sneered in disgust as he placed the glass back in front of Dean.

'Well, that's nice and vague,' Dean said, the corner of his mouth threatening a smile. 'Didn't really think you'd be able to do anything, but it was worth a shot. Crowley'll be thrilled.' He stood and stretched his wings when Lucifer reached out and lightly touched his shoulder.

'I do have one question, though,' Lucifer said. 'Why be friends with a demon? He represents the worst humanity has to offer.'

'Oh, c'mon. There's worse demons than him out there,' Dean said with a laugh. He coughed as Lucifer tilted his head. 'He's just a smarmy, little salesman. Sold his soul for next to nothin', and… Well, he's a full believer in "the enemy of my enemy is my friend", and I'm everybody's enemy. He was nearing the end of his contract, and I was desperate for any kind of affection.'

'So he used you,' Lucifer said, his disapproval clear in his tone.

'We used each other,' Dean admitted with a dismissive shrug. 'He had about a month left when I finally confessed that I couldn't get him outta his contract. Blew up on me and disappeared for a week. Came back and said he'd rather spend his last days with someone he could tolerate. That's why I pulled a few favors and got him fast tracked into the crossroads instead of being tortured for eternity.'

Lucifer huffed in amusement. 'I see. He owes you everything. His allegiance is to you. To an angel.'

'When it's convenient,' Dean said with a shrug. 'Won't just roll over and show his belly. I respect that.'

Lucifer hummed in response. 'I hear he's ambitious. Calls himself "King of the Crossroads"... I wonder if he has his sights set any higher?'

Dean grinned brightly. 'Wouldn't doubt it. Better watch your back,' he said, elbowing Lucifer and imitating the action along their Graces.

Lucifer lightly ran his Grace over Dean's before slowly withdrawing. 'Take care of yourself, Seraphiel,' he said and quickly departed.

Dean crossed the room and joined the others, wrapping his Grace tightly around Castiel's and weaseling his way in. 'That went a lot better than I thought it would,' he admitted. He basked in the reassuring embrace of Castiel's soft love, glad there was no judgement.

Sam waved a hand at the bar. 'Sounded like you guys are making some progress in his rehabilitation. No shouting, some smiles… Looked good.'

Dean nodded as he rearranged his wings a few times. He caught Castiel and Gabriel staring and self-consciously tucked them out of sight.

Gabriel rolled his eyes. 'Whatever, I'm heading back before your surrogate father kills your boyfriend.'

Dean grunted as Gabriel flew off. 'Not my boyfriend.'

'Will you continue driving?' Castiel asked.

Dean caught the utter lack of enthusiasm floating through Castiel's Grace and sighed. 'Fine. You grab Sam. I'll grab Baby.' He waited until Castiel had his hand on Sam's shoulder and readied for takeoff. 'Also, I got Death's location,' he said right when Castiel vanished. He laughed to himself as he felt the shocked remnants of Castiel's disbelief.

.-.-.-.-.

The moment Dean landed in Bobby's living room, he winced at the irritated faces staring at him. 'What? I did good.'

Gabriel spread his arms in a quick motion. 'Not it!' he declared.

Dean rolled his eyes as he tucked his wings away and crossed his arms. 'I'm sure he's not that bad.' He looked to Castiel for confirmation, but received a grimace and shrug in response.

'Death?' Gabriel scoffed. 'Not that bad? I've met him. I've worked with him. He's a bag of necrotic dicks.'

Dean let out an exasperated breath. 'So he rubs you wrong because he follows the rules.' He caught sight of Crowley lingering by the doorway with a raised brow. He shook his head. 'Sorry, man. Talked to Lucifer, and it's a no go on calling off the hunt. Kids are outta control.'

Crowley sniffed in disgust and turned on his heel, narrowly avoiding Bobby as he rounded the corner.

'So you know where Death is? And you're sure Lucifer wasn't lying?' Sam asked.

'Pizza joint in Chicago. And, yeah. Can't lie through Grace. You can omit and hide all you like, but we can't lie.'

'Doesn't stop some of us from trying,' Gabriel grumbled.

'Hey!'

'I said "us"!'

Dean rolled his eyes with a loud huff, ignoring the flashes of memories Gabriel sent of all the lies he attempted before figuring out how to lie through omission. 'Right. So Gabe's out. Sam? Cas? Either of you wanna come with?'

Castiel slowly shook his head, his attention divided.

Dean lightly probed Castiel's Grace, only to find confusion. 'What's up?'

'A resurrection,' Castiel lowly replied. 'I… No name.'

Gabriel groaned as he sunk onto the couch. 'If it's the Second Coming, I'm gonna straight up join the fucking pagans again. Because seriously? Facing Kali right now would be better.'

Bobby looked to Castiel and inclined his head. 'You got an idea when it's gonna happen? Is it something we can camp out and grab up the poor sap that's getting dragged into this?' At the angels' questioning looks, he shrugged. 'Hey, we might get lucky and get someone else to convince to be on our side. You lot brought back Dean. Maybe it's gonna be some great hunter or fighter.' He made a grimace and glanced at Sam and Dean. 'Maybe John. Try and manipulate him into talkin' you boys into doing something stupid.'

Sam sighed as he shared a glance with Dean. 'If they promised him to bring back Mom? I can see that.'

'Then they sure as shit weren't paying attention to the family dynamics, were they?' Dean spat out. He flinched as Castiel rested his hand on his shoulder, love and understanding softly running against him. He pinched the bridge of his nose. 'Right. Yeah. Anything for Dad's approval. I get it. I don't change.'

Castiel gave Dean's shoulder a light squeeze. 'I'll...camp out the site and bring back whoever it is,' he said.

Sam stepped forward and nodded. 'I'm coming with you. If it is Dad, then I can convince him to come without a fight. Hopefully.'

'So that's settled,' Dean said and turned to look between Bobby and Gabriel. 'Any volunteers for my little adventure?'

Gabriel made a show of looking anywhere but Dean.

'I'll join you,' Crowley said, stepping past Bobby.

'Nice to know you were paying attention. You know I'm meeting Death, right? Not going to the ballet.'

'I need to get out of here,' Crowley ground out, shifting his gaze around the room. 'Sadly enough, I'm safest surrounded by beings others are uncomfortable with.'

'Right,' Dean said, drawing out his disbelief.

'The Art Institute of Chicago also has an exhibition I've been meaning to see,' Crowley reluctantly admitted.

Dean snorted and shook his head. 'There it is. Guess I'm looking at art I don't get. This ain't helpin' your tab. You know that, right?'

Crowley tilted his head to the side in acknowledgement. 'I'll introduce you to the curator.'

.-.-.-.-.

Dean landed near the restaurant and released his grip on Crowley's shoulder.

'Nothing like Angel Airways to remind you of how every other form of travel is better,' Crowley griped as he straightened his jacket. He eyed Dean's wings as they were tucked away. 'Although the flight was much smoother than last time.'

Dean threw him an unimpressed stare. He tentatively reached out and confirmed Death's presence.

An inquisitive spark reached back.

'Right. Let's do this.' Squaring his shoulders, he entered the building, Crowley close on his heels. He hesitated when he saw Death sitting at a table for two, casually eating. He swallowed and took the empty seat as Crowley lingered by the doorway.

'By what name should I call you?' Death asked, not bothering to look up.

'Whatever you feel like, I guess. Been getting all sorts of names lately.'

Death nodded to himself before raising his eyes to Dean. 'You gave one of my Reapers a hard time. She was rather put out.'

'Yeah, she proved a pretty good distraction.'

'Quite. We all play our parts in the Prophecies we affect to the best of our ability.' He paused and sat straighter, giving Dean a hard stare. 'Except you.'

'That's me. Fucking up Dad's big plan,' Dean said with false bravado. He distractedly mulled over the implication that Theresa was fulfilling a purpose specific to him.

'Are you?' Death asked, a brow raised in amusement.

'I'm trying.'

Death stared at Dean in silence. When Dean finally looked away in discomfort, he spoke. 'It is not just organisms that fall under my purview. Concepts live as well. Ideas. Hope. Destinies. Nothing is permanent.'

'Great. So can I kill a prophecy?'

Death dabbed his lips with a napkin. 'That, Dean Winchester, is up to you.' He set his ring on the table and stood. 'But the longer the Devil roams free, the more your world will suffer.'

Dean stared at the ring, barely aware of Death's departure. Everything surrounding the apocalypse dealt with Lucifer roaming the Earth. What options did he have? Send Lucifer to Heaven to be murdered? Somehow convince him to willingly stay in Hell?

But wasn't that all just part of the prophecy? Death didn't say he couldn't kill a prophecy.

With a shaking hand, he took the ring.