10 Times Castiel Met Bobby Singer

By Daylight

I.

The first time Castiel met Bobby Singer, Bobby was merely the other man in the room, an obstacle standing in the way of his mission to contact Dean Winchester.

The angel made his way across the rune-covered building, mind set on his heavenly purpose, powers barely contained by his newly acquired vessel. Above him, the ceiling shook and the lights exploded into showers of sparks. The very structure hummed with the energy of his grace. Castiel was there to deliver his message to the one he had raised from perdition and he had no intention of letting anything bar his path.

The man remained at Dean's side standing his ground as he repeatedly fired his rifle never missing his target. Even when weapon proved useless, he still did not back away. When Castiel turned to address his charge, the man swung at the angel with a bar of iron as if a simple human could harm a warrior of the lord.

Despite the attacks, Castiel held no animosity towards the man, but he needed to speak to Dean alone. He caught the iron bar and laid two fingers on the man's forehead quietly commanding his human mind to sleep. The man's body slowly slid to the floor.

And Castiel thought no more on him.

II.

The second time Castiel met Bobby Singer, Bobby never even knew he was there.

Finding himself frequently confused and frustrated by his charge, the angel had taken to observing Dean covertly in hopes of understanding him better. Opportunities were scarce between the numerous battles for seals, but Castiel kept finding more and more excuses to simply watch the Winchesters, unable to deny his increasing fascination with humanity.

On this occasion when he arrived invisibly in their motel room, he found Dean and Sam already in the company of their friend Bobby. The three were researching, seated haphazardly about the room. Everywhere open books were scattered and papers depicting various inscriptions were pinned to walls. They worked intently with only the intermittent exchange of words.

After awhile, Dean casually reached into his duffle bag and without any effort to hide it, pulled out a metal flask. Sam looked up from his laptop and gave him a look of mixed disapproval and disappointment, but Dean ignored his brother. Unscrewing the cap, Dean prepared to drink only to have the flask snatched out of his hand before he could begin to tip the contents into his mouth.

"Hey!" he protested.

"You've had more than enough," replied Bobby. "You're starting to smell like a brewery." The old hunter went over to the little kitchenette and emptied the amber liquid into the sink.

"But…" said Dean, his face still lost in surprise and confusion.

Bobby grabbed one of their many bottles of holy water. "If you're going to have this damn thing," he said pouring the water into the flask, "you might as well keep something useful in it."

"I nee…"

"Don't you dare say you need it!" Turning on him, his eyes fierce, Bobby thrust the flask back into Dean's hand. "Alcohol is not something you need. It is either something you enjoy or else it's something that owns you. You do not need it."

Their eye met with equal stubbornness.

Sam looked from one to the other remaining silent though his troubled face had much to say.

Dean's jaw clenched and his fingers gripped the flask tightly. "You have no idea what I've been through."

"No, I don't. I thankfully have no clue what hell is like. But I do know from experience that whatever happened to you down there, alcohol ain't going to make it any better." Bobby put a strong hand on Dean's shoulder. "You're not in hell anymore, boy, and it's about time you stopped living like you were."

Staring at the ground, his expression closed off, Dean said nothing, but after a moment he patted the hand still resting on his shoulder.

Bobby accepted the small gesture with a nod and let go moving away.

Giving himself a mental shake, Dean looked up as if nothing had happened. "So, we figure out how to kill this banshee yet?"

Head titled to the side as he watched them, the angel frowned. This friend was obviously someone Dean trusted deeply though Castiel could not see why. He made note of it in case it came in useful in the future. Getting Dean to obey orders had proven to be an almost impossible task.

And Castiel wondered why of all people Bobby was the one Dean actually listened to.

III.

The third time Castiel met Bobby Singer, the hunter was once again unaware.

But for the first time, the angel felt like an intruder, very much aware he was trespassing in Bobby's home. The owner's presence was infused into every inch of the building, from the dusty piles of papers and books to the smell of whisky and gasoline to the buried echoes of forgotten hopes and dreams.

And Castiel felt unwelcome.

It was not something he had felt or even thought about before. He usually just appeared wherever he was needed without concern, but now he knew what reaction the humans would have to his unwanted intrusion and he found it hard to dismiss.

Forcing himself to focus on his mission, Castiel made his way though the house seeking his charge, rationalizing away the feeling as just another symptom of the questions that continued to plague him.

Dean had already succumbed to sleep lying still clothed on the couch, but seated at the desk beside him, Bobby remained awake. The old hunter continued to peruse his books intent on finding a way to the help Sam.

Needing to guarantee the man wouldn't interfere with his task, the angel was forced to use his powers to send him to sleep a second time. Bobby's mind fought back, but his eyes soon blinked shut and his head slowly fell forward to rest on the open book in front of him.

As soon as Bobby was asleep, Castiel flew past down to the basement to complete his unfortunate orders, ignoring the stirrings of more doubt inside of him.

The angel hadn't been surprised to find the Winchesters with Bobby once more. After keeping careful tabs on Dean over the past year, he had found the brothers always turned to Bobby whenever things were at their worst.

And Castiel wondered what it was about Bobby Singer that made them have so much faith in him.

IV.

The fourth time Castiel met Bobby was also the first time they actually spoke.

And unfortunately, the angel immediately found the older hunter's attitude to be very similar to that of Dean's, but by that time, he was used to the language and the general lack of respect.

Despite the attitude, Castiel was honestly sorry the man had lost the use of his legs. It was also a sharp reminder of his new limitations. He might still be an angel, but there was nothing he could do to help Bobby and he was beginning to feel more foreign emotions, helplessness, guilt.

"You're telling me you lost your mojo just in time to get me stuck in this trap the rest of my life?"

"I'm sorry."

"Shove it up your ass."

The man wrapped his pain and disappointment in anger and turned his back on the angel only tiredly joining in again when the conversation turned to other concerns.

Castiel had heard how the injury had occurred whispered through one of the few sources he still had available to him. It was a rare human that could resist the possession of a demon though there was little of that power visible now in the figure sitting hunched in the wheelchair.

Bobby had done it to save Dean.

And Castiel wondered where the human had found such strength.

V.

The fifth time, the angel came searching for information.

His resources now limited, Castiel arrived to ask a simple question. According to Dean, Bobby knew everything. Despite the many tomes of knowledge haphazardly piled about the hunter's home, Castiel found that unlikely. Still, he trusted Bobby being their friend would know where the Winchesters were. He hadn't, however, counted on the old hunter's protectiveness and paranoia.

"So Dean should just drop everything and help you on your little quest? You didn't seem very interested in helping him in his plans to defeat Lucifer."

Castiel bristled fighting to retain his usual calm. "Dean insists on a futile course of action. It is not possible to defeat Lucifer without God's help."

"You'd be surprised by what that kid can do when he sets his mind to it."

"He does often seem to manage the impossible," Castiel replied glancing away.

Bobby snorted. "Then maybe you should have listened to his ideas before blaming the boys for everything your lot started."

The fire of his temper burned growing uncomfortably uncontrollable and Castiel glared at the human. "They're not 'my lot' anymore. Besides you yourself don't appear to be doing anything to help Dean."

Instead of flinching away, the man met his gaze with equal fury. "In case you've forgotten, I'm stuck in this fucking chair!"

"And that's preventing you from aiding them? I did not know all your wisdom lay in your legs."

"You don't understand!" Bobby's voice bled from anger to despair. "I'm not good for anything but demon bait like this. The frigging apocalypse is on us and all I can do is answer questions over the phone!"

The wheelchair spun away as the man escaped out the door, but before Bobby broke his gaze, Castiel caught a glimpse of his soul. It was the bright shattered soul of a weary warrior feeling helpless under the weight of growing darkness.

And Castiel wondered how an angel and a human could have so much in common.

VI.

The sixth time, the hunter called him.

The Winchester brothers had been missing for three days. Bobby did not so much ask as order Castiel to find out 'what trouble those idjits had gotten themselves into this time.' Part of Castiel, the part that had long sat above the world in the choirs of heaven, felt he should feel affronted by being ordered about by a mere human, but another part, a part that was softly becoming more human each day, realized this was just Bobby's way. Besides that part of him was worried about Dean and Sam too.

So the angel set off to find the Winchesters.

After it was all over, Sam and Dean were safe, and Castiel was once again reeling with disappointment in another one of his brothers, the angel dropped in on Bobby to let him know all was well.

Closing his eyes, the old hunter's whole body sagged as the tension left him. He reached for a bottle of whisky and poured it into a glass with a shaky hand.

"Those boys are going to be the death of me," Bobby said and threw back the shot. He offered the bottle to the angel but Castiel shook his head. "At least, this time they came out intact."

"They are physically well though Dean was complaining repeatedly about the psychological trauma of never being able to enjoy his favourite TV shows ever again."

"Sounds like him." The hunter snorted. "Can't say I ever figured that Trickster for an angel though," he commented giving Cas a sideways glance.

Castiel looked into the distance. "Gabriel always had a thing for poetic irony." He said no more trying to shut out the memories of a brother he'd looked up to long ago, who'd tried to bring laughter to heaven and dared speak out against the bitter fighting; then vanished without a word.

"Hey," Bobby called out breaking Castiel from his thoughts. "Thanks."

Castiel frowned. Gratitude was not something he was used to, from heaven or earth.

"They're all I have left." Bobby sighed looking down at his empty glass. "If anything happened to them…"

The angel nodded, the depth of Bobby's feelings for Sam and Dean hitting him for the first time.

And Castiel wondered how such a love could survive all the pain and darkness of their turbulent mortal lives.

VII.

The seventh time Castiel met Bobby, he stayed the night.

Weeks spent searching for the Colt had left the Winchesters weary and even Castiel was feeling tired, the new limits to his powers weighing on him, so they stopped over at Bobby's to rest. The angel had only intended to ensure the brothers' safety, but before he knew it, Sam was setting up a place for him to sleep on the couch, Dean was forcing him to change into an old pair of clothes, and Bobby was joking about angels snoring.

Though he was tired, he lay on the couch a long while simply staring at the ceiling, preoccupied by novel sensations, the feel of different clothes on his skin, even the simple act of lying down was still new to him. The night left the house cold and dark and it creaked ominously, but Castiel could sense the presences of the others in the house. Dean and Sam remained faint hidden by the Enochian sigils, but Bobby's soul still shone brightly. The familiarity of the presence brought comfort, and focused on that, he let his body shut down and his mind fall into unconsciousness.

When morning came, Bobby insisted the angel join them for breakfast despite Castiel's protests that he didn't require food. Suddenly, the angel found himself enmeshed in the midst of their routines, between coffee, bantering, sausages and dishes. He became lost in the human rituals, not quite understanding their purpose, but the others seemed to relish every little moment as if it was all they had. These simple things made them happy and Castiel could feel the peace and contentment wash through them into him.

As they left, Bobby called out for them to come back anytime they needed. It wasn't until hours later and on a different continent that the angel realized the hunter had meant him too.

And Castiel wondered if this was what humans meant when they spoke of home.

VIII.

The eighth time Bobby came to their aid.

Proving that even a wheelchair couldn't stop him from saving their butts as he himself said, Bobby arrived just in time to rescue Castiel, Dean and Sam from a trap set by a group of demons who'd unfortunately proven cleverer than most. The old hunter then spent half an hour yelling at them for being careless 'idjits'.

Castiel took the tirade stone faced while Sam and Dean looked suitably contrite gazing at the carpet. Once Bobby was done and had left the motel room for some fresh air, the angel turned to the Winchesters.

"I don't understand why he's so angry. It was not our intention to be caught by the demons."

The brothers exchanged knowing smiles.

"He's not really angry," explained Sam.

Castiel's forehead furrowed. "Then why was he yelling?"

"He's only yelling because he was worried about us," said Dean.

The frown remained fixed on Castiel' face.

"It's how he shows he cares."

"By yelling?"

The brothers shrugged in unison.

"I wouldn't have to if you three boys bothered to look after yourselves!" Bobby yelled from outside.

And Castiel wondered when he had become one of Bobby's boys.

IX.

The ninth time was on the eve of battle.

It was a gathering of warriors with Bobby's home as their base.

Castiel watched from a distance as the Harvelle women were greeted like long lost family. The angel watched as Bobby grumbled half-heartedly when Jo kissed his bearded cheek, as Ellen laughed with a wide smile and met Bobby's gruffness with a spirit equally strong, as Jo smirked and saw through everything Dean said, as Ellen looked Sam over carefully as if she didn't believe him when he assured her he was fine.

And Castiel was welcomed, thrown into the joking and the drinking. Thanks to Ellen, he consumed a surprisingly large amount of alcohol and marvelled at the strange tilt it added to the world. Smiles were exchanged. Stories were shared. Jo happily regaled him with the tale of how she'd first met Dean and how she'd almost broken his nose. Dean looked sheepish. Sam gave a rare laugh.

They were trying to forget what they would be facing, but Castiel's mind didn't let him forget. He knew what was at stake. He knew the consequences. They knew too, but still their souls resisted the darkness.

Bobby remained slightly apart unable to hide his bitterness at having to stay behind. He tried to hide his fear too, but Castiel could tell by the way he hustled them into position for a photograph, that the hunter was afraid the photo would be all he'd have left.

Near the end of the night, Bobby broke the warm drone of conversation by raising a glass and said, "To us, the best of the best, the ones who keep going no matter what. Here's to kicking that devil in the ass."

With cries of agreement, the others raised their drinks too and in that moment, it seemed as if they were unstoppable.

Then it all went wrong.

When they returned, Castiel watched from distance as Bobby rolled up to the brothers reaching for their arms and yanking them down to his level so he could grasp them tightly. Castiel watched as Sam and Dean told their tale and Bobby's face crumbled with sorrow and despair. And as the angel watched, Bobby turned and caught sight of him. The expression on his face might have been one of relief, but all Castiel felt was the sharp cut of grief and it was too much. He fled to the roof.

While Bobby and the Winchesters said their goodbyes inside, Castiel stood on guard above watching the stars. The ever-present darkness of the apocalypse was growing heavier.

And Castiel wondered how any of them could keep going when they had lost so much.

X.

The tenth time was unintentional.

He'd been caught, his brothers and sisters surrounding him, heavenly warriors straight-backed and sure of their convictions. They fought with the confidence of those who had battled evil for millennia, and now, to them, Castiel was that evil. Powers still diminished, Cas fought back with even greater ferocity until he could fight no more; then injured, he fled.

Desperate to lose pursuit, he flew from place to place, island, desert, city, mountain, until his wings gave out and he found himself falling to his knees, his palms scrapping against the ground beneath him. Exhausted, he knelt there breathing heavily, blood dripping from his wounds, without the strength to even raise his head. It wasn't until he heard the sound of wheels scrapping through gravel and a familiar gruff voice above him that he realized where he was.

"Hey, Feathers. You okay? Cas?"

All Castiel could do was shake his head.

"Well, I can't have you bleeding on my driveway, so you'd better come inside."

Cas felt the urge to laugh. It was so sudden and strange it terrified him.

"Come on. You'll have to lean on my chair. It's not like I can carry you."

The angel reached up and grabbed the handle of the wheelchair slowly pulling himself onto shaky legs. For a moment, the world spun and darkened at the edges. When it finally settled and Cas came back to himself, he found he was leaning heavily against the chair and Bobby was staring at him with eyes full of worry. The man held tightly on to him with one hand while the other kept the chair steady.

"You're going to be fine, Cas. You hear me? Just make it to the house and I'll take care of you," said Bobby both as a command and a plea. "Ready?"

Cas took a deep breath and nodded.

As they slowly made their way towards Bobby's home, the only thing the angel was aware of beyond the pain and exhaustion was the voice encouraging him to keep going and telling him everything was going to be alright. It pulled him forward through the darkness.

And Castiel finally understood.