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The first time it happened, Dean was 18 and fresh out of high school. It was a hot and sunny summer day and he had been skateboarding. The skatepark was relatively busy that day. Dean had a crush on a boy named Lee who also happened to be there. Dean had been working on a new trick for the past few weeks and he decided to try it out to impress Lee. Dean was anything but smooth, he fell off his board and was falling head first toward one of the stone ramps in the middle of the park. At the last second, it was almost as if he was pushed and he managed to clear the ramp and not crack his head open. He brushed it off as pure luck. The only thing he hurt that day was his dignity.
The next time it happened, Dean was a freshman in college. He never expected to go to college, let alone make it through an entire year of college. He had finished taking his last final earlier that day and decided celebratory drinks were in order with his friends. He threw on a light jacket and walked down to the bar down the street from his apartment. It was a nice night in April, not too cold and the sky clear enough that he could see the stars perfectly. He met his friends inside the bar and ordered a beer. They all revelled in the fact they were done their first year of college. Summer plans were made and several rounds of drinks were ordered.
By the time he left the bar, Dean was pleasantly buzzed. When he started his walk home he took in the cool spring air and smiled. He crossed the road but didn’t look before he started walking across, who would be out on the roads in a small college town at one in the morning anyway. The Honda Civic that came at him at 50 kilometres an hour was who. Dean saw headlights and thought he was a goner. He squeezed his eyes shut and felt pressure between his shoulder blades and was being thrust across the road, away from the car. He opened his eyes, finding himself on the other side of the street, his only injury a scraped palm. He thought back to the skateboarding incident and wondered if this wasn’t a coincidence. Dean remembered he was sitting on the edge of the sidewalk and got up to walk home. He decided he’ll think about this more in the morning.
Throughout Dean’s college years he continued to find himself in unfortunate situations, some of which he probably shouldn’t have survived. Most notably the car accident that totaled his car but didn’t leave a scratch on him. People said to him “it’s like you have a guardian angel watching over you”. He laughed them off and said that was insane. His mother told him when he was young that angels were watching over him. But there was no way angels were real, no especially not after what happened to his mother. If angels were real they would have saved her from that fire.
Dean, in his fourth year of college now, returned to the street where the car almost hit him three years ago. He looked up at the sign this time, it was the corner of Lawrence and 5th Avenue. He sat against the wall of a convenience store, bottle of whiskey in hand. The anniversary of his mother's death always hit him hard no matter how many years had passed. Coming back to the spot he was almost killed was perhaps not the smartest thing he could’ve done but hell was it poetic. Whatever my guardian angel will protect me he thinks sarcastically, taking another swig of whiskey. There was no one else on the street considering it was 11:30 at night on a Tuesday, although that’s what he thought last time. Suddenly, a man materialized before him, he was tall with unruly black hair and kind blue eyes. A kind smile played on his lips and he was dressed in a suit with a trench coat over top. Dean stared. He rubbed his eyes. Nope, the guy was still there.
“Did you just-” Dean couldn’t even finish his sentence.
“Hello Dean,” the man said.
“How the hell do you know my name?” Dean asked.
“My name is Castiel, I’m your guardian angel” he responded.
“God I really am drunk” Dean murmured and leaned his head back against the wall and closed his eyes. He couldn’t believe this, there was no way angels were real.
“Dean, I assure you I am real”.
Dean felt a hand on his shoulder. He opened his eyes to Castiel crouching in front of him with a look of pity on his face. Dean felt strangely connected to the man, or angel rather. He decided to trust him. He felt his eyes start to water.
“Why now?” Dean choked out.
“I figured you could use some company tonight,” Castiel answered.
Dean moved over in silent invitation for Castiel to sit down next to him. Castiel first took off his jacket and draped it over Dean’s shoulders. Castiel sat down beside him and Dean leaned his head against his shoulder, tears silently running down his face. Dean lost track of how long they had been sitting in silence but it wasn’t awkward, it was peaceful.
“So have you just been following me around my whole life?” Dean asked, breaking the silence.
“I swore to protect you after your mother passed, heaven commanded it” Castiel explained.
“Great, my guardian angel wears a trench coat,” Dean said with a slight smirk, his eyes still glassy with tears.
Castiel smiled at him and put an arm around his shoulders. Dean leaned into the angel and decided to save all his questions for when he was sober. Eventually, Dean’s eyes started to get heavy and Castiel told him it was time to go home. They walked back to his apartment together. Dean got ready for bed and Castiel waited outside his room. He climbed into bed and Castiel entered the room.
“You my roommate now? ‘Cause, you’re gonna have to start paying rent” Dean said sleepily.
“Go to sleep Dean, we’ll talk in the morning” Castiel responded.
“M’kay night, Cas,” Dean said as his breathing evened out and he fell asleep.
“I’ll watch over you,” Cas whispered.