A/N: For NordicRivers, who wanted Cas and Bobby friendship. Set after 5x16 and kinda in the middle of 5x17 "99 Problems."

Disclaimer: Not mine. Thanks to 29Pieces for beta reading and one of Bobby's lines!

"Whiskey and Wisdom"

Bobby thunked the book he was reading on the desk and rubbed his eyes. When words started blurring together, it was time to call it a night. He wasn't getting anywhere anyway. More omens, more portents of doom, more big fat zero on stopping any of it.

He turned his head toward the pile of blankets on the couch that was his makeshift bed since the wheelchair. Somehow, wheeling the three feet over to it and then lifting himself out of the chair seemed too exhausting. He opted for opening the bottom drawer in his desk and pulling out the bottle of whiskey and rocks glass he kept there.

Before he could pour himself a drink, however, there was a thud from the kitchen that had him reaching for the shotgun under the desk instead. He whipped it out and up, aiming at the dark figure shambling in the shadows. Bobby tensed.

But then the intruder lumbered under the archway, and Bobby registered the tan trench coat first—it was a good thing the stupid article was so recognizable. He lowered the shotgun.

"Can't you knock?" he groused.

Cas caught himself on the dividing frame between the den and the kitchen, and Bobby's guard instantly went up again.

"What happened to you?" he asked, stowing his weapon back under the desk. And was he gonna have to clean it up?

Cas blinked at him through bloodshot eyes. "I drank a liquor store. But it didn't work, so I thought I would come here and…" He lurched away from the wall and stumbled forward, bumping into the back of the chair on the other side of the desk. "I thought I would come here and find out what the proper brand is, the one you and Dean use." His gaze landed on the whiskey bottle, and the angel took one more drunken step before plopping heavily into the chair. "What is that and where do I find it?"

Bobby just gaped at him. What in the hell…? "Are you kidding me?" he nearly shouted. "The end is nigh and you're off getting hammered?"

Cas tilted his head sideways to blink at him, except his head kept going until he almost fell out of the chair. But he caught himself and straightened. "There's no stopping the Apocalypse. And isn't that what you were about to do?"

Bobby didn't have a response for that, so he snapped his mouth closed. Shit, when an angel went on a bender, he knew they were royally screwed.

"Will that brand make the pain stop?" Cas asked.

Bobby furrowed his brow. "What?"

Cas was sinking down in the chair again, and even without smelling like he'd bathed in booze, he looked a complete wreck, his eyes wavering with a vulnerability that hadn't been there when he'd first stumbled in to disrupt Bobby's quiet evening. "Dean drinks to forget his pain. I drank, and drank, but I didn't forget. The pain is still there…just blunted. So how do I forget?"

Bobby's shoulders sagged. Aw, hell. He'd gotten a recap from Sam about what went down when he and Dean had "died and gone to Heaven," and not in the fun sense, including how God didn't give a shit about any of them. Guess it was hitting the angel pretty hard.

Bobby turned his wheelchair around and reached for another glass tucked behind some books on the shelf. He plunked that down on the desk, and poured both him and Cas a full glass.

"Forgetting only comes when you drink yourself unconscious," he said.

Cas's brows knitted together. "Oh." He looked down at the amber liquid in his glass. "How much more do I need, then?"

Bobby snorted. Given what the angel had said about the liquor store…too much. He felt an odd pang of sympathy for the poor bastard. "Look, Cas…it ain't gonna make you feel better."

The angel squinted at him. "But you and Dean do it. So does Sam sometimes."

Bobby let out an exasperated sigh. Yeah, and now they were teaching an angel to become an alcoholic. If they weren't going to Hell before, they sure were now.

"It ain't gonna solve your problems," Bobby replied, ignoring Cas's point. "So your dad's a deadbeat. Mine was an abusive son-of-a-bitch, and not to speak ill of the dead, but John wasn't exactly winning any awards with Sam and Dean. Welcome to the club."

Cas stared morosely at his glass. "My life…my entire existence, has been a lie."

Bobby scoffed. "So, you choosing to side with humanity against the Apocalypse, standing up for what's right when no one else would, is a lie?"

Cas's face scrunched up.

"We don't get to choose our parents." Bobby paused, then added, "But sometimes we get to choose our family."

Cas lifted his gaze and stared quizzically at him.

"Sam and Dean, the way they've grown attached to you…that ain't a lie." And, if Bobby cared to admit to himself, he'd grown somewhat attached to Feathers too.

But he didn't admit things like that.

Cas's ruminative look turned inward, and Bobby went back to nursing his own drink in silence. After a while, Cas pushed his half-full glass away. "I believe I may have poisoned my vessel."

Bobby snorted. "Yeah, wouldn't surprise me." He shook his head at himself and gestured to his bed. "Just go ahead and sleep it off." He hadn't been planning on using it tonight anyway.

Cas's gaze slowly tracked toward the couch. "Angels don't sleep."

"They don't get hammered, either."

Cas frowned. "I should probably go…" He started to rise from the chair unsteadily.

"Sit your ass back down," Bobby ordered.

Cas abruptly did so, and blinked at him in bewilderment.

"Haven't you ever heard 'Don't drink and fly'?"

Cas stared at him owlishly. "No."

"Well, make a note of it." Bobby wheeled his way around the desk and over to the angel. "Now come on, let's get you to bed."

The angel seemed a rather docile drunk, obediently bracing one hand on the arm of the wheelchair to lift himself up. Bobby took Cas's elbow to help steady him as he staggered to the bed and collapsed face first onto it. With a sigh, Bobby rolled back to his desk, but as he considered the bottle of liquor, he couldn't help but hear his own words echo back in his head.

Balls.

He capped the bottle and put it back in the drawer, but at least finished off his one glass. After all, he certainly wasn't a saint.

The next morning, Bobby had a full glass of water and ten aspirin ready for when Cas finally woke. He figured if it'd taken an entire liquor store to get the angel smashed, it'd take more than the standard two pain relievers for the bitch of a headache Cas was gonna have.

Sure enough, the angel groaned as he shifted on the couch.

"Here." Bobby practically shoved the cup of water in his face once he sat up.

Cas squinted at it for a moment before wrapping his fingers around the glass and taking a sip. "I'm beginning to regret the liquor store," he grunted.

Bobby tried hard to hold back a snort at that, and dropped the pills in Cas's other hand. "Swallow these, too," he instructed.

The angel stared at them for a delayed moment again before popping them all in his mouth.

"Water," Bobby prompted so he wouldn't attempt to swallow them dry. Cas dutifully knocked back a long drag, face scrunching up as he did so. He then drained the glass.

"Thank you," he rasped.

Bobby shrugged off the gratitude. Cas's phone rang then, and he fumbled in his pockets searching for it.

"It's Sam."

"Better answer it. Those boys might need you," Bobby said pointedly, trying to convey more than that, though there was no telling whether Cas even remembered last night.

The angel flipped his phone open to answer, but didn't put it to his ear right away. Instead he gave Bobby a considering look, and slowly nodded.

Sam's faint voice repeating Cas's name from the speaker finally caught his attention, and Cas lifted the phone up. "Hello, Sam."

Bobby turned and wheeled back over to his desk while Cas made mumbled affirmations and then said he would be right there. A puff of air buffeted his back, and when he turned around, Cas was gone.

Castiel needed to return to Heaven, needed to spread the message of free will that God had decreed by resurrecting Castiel after Stull Cemetery. But there were a few things on Earth he wanted to check on first. Dean had gone to join up with a past love interest as a kind of fulfillment to Sam's last wish before his brother had jumped into the Cage. Castiel had made sure Dean made it without any trouble, and then he'd flown to Bobby Singer's house.

Castiel pulled up short upon landing in the kitchen, however, when he found the older hunter passed out at the kitchen table, an empty bottle of whiskey by his head. Castiel frowned. Had Bobby drunk that whole bottle on his own? Why?

He took a step forward, only to freeze when Bobby made a gurgled noise in his sleep.

"Ungh, S'm?"

Castiel's heart fell. Of course. Dean wasn't the only one who'd lost a member of his family.

He drew his shoulders back and tentatively called, "Bobby. Bobby."

The grizzly hunter made another garbled sound, his eyelids fluttering. "What?" he growled, struggling to lift his head and blink blearily. "Oh. What do you want?"

"I came to make sure you were okay," Castiel replied, and hesitated. "You're not."

Bobby winced and squeezed his eyes shut. Castiel remembered what that kind of throbbing pain felt like, and he moved forward with two fingers outstretched to heal.

Bobby jolted and smacked his hand away. "What in the hell do you think you're doing?"

Castiel quirked a perplexed brow. "I can heal you now."

"You touch me with that mojo and I will kick your ass so hard you won't fly straight for a week," Bobby snapped. "I worked hard to get this drunk, and you ain't gonna take it away from me."

Castiel frowned. He assumed Bobby was attempting to deal with his grief over losing Sam. "You once told me this method didn't work."

"I lied," the hunter grumbled.

Castiel canted his head in confusion. "I am fairly certain you didn't. I remember…being drunk didn't make me feel better." In fact, it'd made him feel much worse afterward.

Bobby grumbled something under his breath. "Just go."

Castiel hesitated, torn between doing as he was told and…not. Because Bobby was his friend and was hurting. And so Castiel quickly made a decision. He moved forward and grabbed the hunter's arm to sling him over his shoulder.

"What are you doing?" Bobby exclaimed just as Castiel flapped his wings and flew them upstairs. Bobby lurched violently, and Castiel dropped him onto the bed. He was still cursing, but his words were too slurred for Castiel to make them out.

"Sleep it off," he said.

Bobby might have insulted him in response, but Castiel ignored it. He flew back downstairs, filled a glass with water from the tap, and searched the cupboards until he found a bottle of aspirin. Then he returned upstairs and set them on the bedside table. Bobby was already out, soft snores wheezing from his nose.

Castiel looked around the small bedroom, his senses picking up how empty the rest of the house was, how quiet. Sam was gone. Dean had left.

He spotted a worn photo on the dresser, and went over to get a closer look. It was of Bobby, who looked much the same as he did now, but there were two young boys in the picture that Castiel would recognize anywhere. Sam and Dean. They were all smiling.

Castiel picked up that photograph and set it next to the glass of water and pain relievers. Both Bobby and Dean were lost without Sam. And though the world was no longer facing an Apocalypse, it was also better with Sam Winchester in it. Besides…Castiel missed him too.

And so he decided he would raid Hell once more, and bring their long lost family member home.