Chapter 1: A Desperate Hour
Long before his messed up life made him into a cynical force to be reckoned with, Dean Winchester had strong faith. It was the only thing that kept him going in a world of so much sickening evil. When the motel cabinets were empty and he was stretching his last dollar to buy Sam a bag of potato chips from the local gas station, it made his job a little easier knowing there was someone out there besides his father looking out for him.
In all of his family's turmoil, Dean had to admit that he didn't see a light at the end of the tunnel. His only hope was to run away from the world and settle down with a ordinary girl. So he prayed for a way out of his life. All he wanted was for some nice girl to come along and love him. Of course, no one would give Dean more than one night stand with his level of emotional baggage. Some kids he knew may have also come from bad home lives, but no one had to deal with the ghosts that he did.
From town to town, Dean would ask for guidance in his life as often as he could. Sometimes he could feel the Holy Spirit with him; other times, he couldn't. Nothing ever changed. Until one fall evening in 1996.
Dean had just dragged in late that evening after a salt and burn in Pontiac, Illinois. Sam was already asleep in the motel room as a result of working hard all day at school. Their father was somewhere a few towns over tracking a kitsune.
He was almost ready to turn in for the night when he heard an electric spark from behind. Several explosive sounds followed, and Dean began to wonder why Sam wasn't awake. His hunter reflexes should be going haywire, but for some odd reason, Sam didn't move an inch. Dean pulled the .45 that he always kept nearby, and instinctively aimed at the lamp light that flickered off only moments before.
Dean suspected demons were behind the electricity problems, but second-guessed that observation when he realized the doors and windows were already salted. Surely, Dean looked like a madman, waving a gun wildly at the ceiling without a clear target.
"Hello, Dean," a gravelly voice came from behind him. Dean spun on his heels in surprise and readied himself to fire on this potential threat. Through the dim light from the outdoor lamp post, he observed the shadow. Dean slowly realized this person must be harmless. If he were going to hurt someone, he would have already made their move.
Dean lowered the gun and asked, "Just who the hell do you think you are?"
"I am Castiel," a young man replied dryly. He stepped out of the shadows to reveal that he had dark hair and a muscular frame hidden under a tan trench coat.
"I mean, what are you?" Dean pressed, his voice rising.
Castiel's head turned slightly, knitting his eyebrows in confusion. As if Dean didn't know who he was. After all, he had prayed for him. Castiel examined the abyssal green eyes before him, but couldn't find any evidence of recognition. He sighed. This was going to be a long night of explanations. "I'm an angel of the Lord," Castiel informed him. "You requested guidance in your endeavor of seeking true love."
"So... what?" Dean asked in confusion. "I pray for love, and the man upstairs sends me a wingman? Literally. What makes me so special?"
"The Lord works in mysterious ways, Dean," Castiel responded in a textbook answer. Dean was so frustrated at the moment, but he couldn't tell Castiel to fly on up back to Heaven. He needed an escape from this life. He needed love. "God cares deeply about you," Castiel continued.
"But why me?" Dean pressed further. "I mean, if He fulfills every promise, what about these drunken lovesick schmucks out on Valentine's Day? What about them, huh?"
"As I said, He works—" Castiel began.
"In mysterious ways," Dean finished sarcastically. "Yeah, I know."
"There are plans for you, Dean Winchester. Very important plans," Castiel said suddenly with a tone of urgency in his voice. "So I suggest that you forget your blasphemy and listen to what I am saying. I am here to find you a suitable mate. One which will give you the love and companionship you are seeking. Now, I propose we get started right away, but it seems in the mortal world of high school, many of you are in the business of procrastination."
"Yeah, okay," Dean agreed, slowly warming up to the idea of having his own guardian angel be his matchmaker. "What are you, some kind of cupid or something?"
"No," Castiel answered solemnly. "I am a soldier."
"Then why did God send you to take care of me?" Dean asked in confusion. "I mean, isn't that more of a job for the guys with fluffy wings and a bow and arrow of love?"
"As I have said before, my Father works in strange ways," Castiel clarified. "However, what I do know is that I was sent here to guide you. I'm just following orders," he said simply. Dean nodded in understanding, but still found himself questioning in the back of his mind. "And for the record, there are many cupids that are lower-order angels scattered around the globe. Why they were not sent in my place is beyond my comprehension."
"Okay, so... you said your name was Castiel?" Dean asked. He was internally generating a nickname for him that would be easier to remember. Nerdy Dude With Wings was fitting, but most definitely too long.
"Yes," he replied.
Dean thought for a moment and asked, "What name is in the school directory?"
"Jimmy Novak," Castiel answered, glancing down at himself. "This is... a vessel."
"You're possessing some poor bastard?" Dean asked incredulously.
"To be fair, he is a resident of Pontiac, Illinois, and he does attend this high school," Castiel explained.
"What about his family?" Dean questioned further.
"He is currently in the custody of his great aunt," Castiel responded. "She is a very kind woman, though she is known for her alcoholism. Most likely, she is in a drunken stupor as we speak."
"Okay," Dean said in acceptance. "Let's get this show on the road."
"Not so fast," Castiel said, stepping forward to rest a hand on Dean's shoulder. "I must work with and understand you before I can assume my duties as matchmaker."
"What?" Dean snapped. "But I need help."
"Oh, you most definitely need help, Dean Winchester," Castiel replied. Dean wondered if it was possible for an angel of the Lord to understand sarcasm. Maybe Sassy Cassy... Cas. "I am here to remedy that," he continued. "However, you cannot truly know a person until you've seen how they react to the best and the worst circumstances. In other words, I must be in your presence quite often. Now, if you don't mind my asking, what kind of time frame am I working with?"
"As soon as possible," Dean said.
"Well, I suggest that you complete your homework first," Castiel demanded.
"Dammit, Cas," Dean growled. He suddenly wondered why he said the pet name aloud. "I didn't ask for this. I need someone to fix me up with a girl."
"I understand, Dean," Castiel said slowly, but Dean knew he actually didn't understand. "There is much more to a relationship than beauty and sex. You must consider your own personality a reflection of what lies deep within. When you learn yourself, then you can learn how you best interact with other people."
"Would you stop with the mumbo-jumbo crap?" Dean begged in exasperation.
"For example, you seem to be an extrovert, but underneath your hyper-masculine shell, you draw your true energy and peace from inside," Castiel said, his bright blue eyes narrowing as he began an analysis on Dean. "Let me guess. You love your small circle of family, but you prefer to be alone. Put on your headphones and crank up the Black Sabbath on your Walkman?"
"Cas," he pressed angrily. "This isn't funny. I don't like this whole psychic thing."
"I agree. This is a moment that can be spared of laughter," Castiel said dryly. "Also, if you ever run across someone who claims to be psychic, they are most likely pathological liars with a need for attention. True psychics are rare and have a very special ability—"
"Enough!" Dean whisper-shouted in exasperation. He lowered his voice, careful not to wake Sam. "Spare me the details about freakin' psychics and stop analyzing my personality. Okay? It's just creepy. You might be here to snag me a lady, but while you're here, you're human. And that means you've gotta fit in."
"Of course," Castiel agreed solemnly.
"That means you've gotta ditch that trenchcoat if you don't want your head to end up in a toilet bowl," Dean snapped. "And no formal sentences. No one actually talks like that in real life."
"Okay," Castiel replied dutifully. "We will start first thing after school tomorrow. In the meantime, you must rest."
"What about you?" Dean asked in concern.
"I'll watch over you," he responded without hesitation.
"That's... not going to happen," Dean concluded. There was no way he was going to let this random dude watch him as he slept.
"Sure it is," Castiel said simply. "I don't sleep. I'm an angel, remember?"
Dean nodded to acknowledge that he remembered this fact about angels. Then he frowned as he realized a certain fact about humans—specifically, his father's conservative views. "Yeah, but if my dad comes back and sees you here, I'm fresh meat," Dean said, his voice lowering to compensate for the subject matter.
Castiel narrowed his eyes as though asking a silent question. "Why? Because I'm an angel? Or because I'm in a male vessel?" he asked aloud to clarify what Dean couldn't bring himself to communicate.
He swallowed his pride and shortly answered, "Both." Dean failed to elaborate, but Castiel instinctively understood. "Now do us both a solid and book a room," he ordered.
"I don't understand how to 'book a room'," Castiel complained. "This is never a problem I have encountered as a soldier of heaven."
"Yeah, well, there's a lot of things you have to do now that you're an honorary human," Dean informed him sarcastically. "Like sleep, for instance. Humans need sleep to function normally."
"Yes, I know how the process of sleeping works, Dean. The problem lies in the cognitive structure of my brain. I do not require—"
"Fine. But if you stay here for the night, you can't wake my brother up."
"Oh," Castiel said solemnly. "So this is Sam Winchester?"
Dean paused in reluctance to discuss Sam with this strange new boy. "Yeah, that's Sammy, my kid brother."
Castiel shrugged quickly. "Nothing," he confirmed. "I've only heard you speak his name via prayer."
"So anyone with a halo and a harp can hear my prayers?" Dean asked.
He hesitated in his answer. "No," Castiel said slowly as he began to explain. "For one, we do not all have harps. Angels are warriors of heaven. Take Matthew 13:49. 'So it shall be at the end of the world; the angels shall come forth, and sever the wicked from among the just.' We are more than good samaritans. We fight for what is just and moral. Secondly, not everyone can hear your prayers. God hears and answers all prayers. However, you can also direct a prayer to a specific angel if you wish."
Dean was silent for a moment as though digesting this new information. So every time Dean was in pain or troubled by life's burdens, Castiel was able to hear him? "Is that how you heard me?" Dean asked in curiosity.
"Of a sort," Castiel answered ambiguously. "Although I have never heard you speak before today, I have heard your destiny; it is a grand and noble one. You are very important in executing the end of days."
"What?" Dean questioned hotly. "I'm a puppet in Operation Apocalypse? Sorry, but I don't believe in destiny."
Castiel tilted his head in confusion. "What do you believe in?" he asked.
"Free will," Dean said firmly. "Family. Loyalty," he continued. "I believe God has granted us free will to test humankind's loyalty to Him. We choose our fate. We choose our ending. You have to choose every day whether you're going to roll over and die or keep fighting. One thing's for sure, I'm going down swinging."
"That's an interesting concept," Castiel said, pondering this new idea of free will. "I hope that when the time comes, you'll be able to stay true to your values."
They sat in an increasingly awkward silence, with Castiel eyeing Sam's sleeping form suspiciously and Dean staring at the glowing streetlight outside, illuminating the motel room with a dim light. "Alright, well, it's getting late," Dean said when he reached his breaking point of silence. "We have freakin' school tomorrow, and I need to help you blend in."
"Okay," Castiel agreed. "You go on to sleep."
Dean balked at the direct order from this intriguing new creature. "What are you going to do?" he asked.
The angel politely took a seat on edge of the twin bed. "I just thought I would sit here quietly," he replied. Dean hesitated but began to warm to the idea as he realized how tiring his most recent hunt had been. He yawned and let his exhaustion prevail as he crawled onto the mattress and let sleep overtake him.