((Author's Note: This is my first attempt at writing fanfiction, so please don't judge me too harshly. All credits belong to Eric Kripke and the writers of Supernatural))

~Cas' POV~

Castiel stood on a rainy sidewalk, picking at his guitar and trying to make his voice heard over the rain.

And they say, she's in the class A team
Stuck in her daydream, been this way since eighteen
But lately, her face seems
Slowly sinking, wasting
Crumbling like pastries
And they scream
The worst things in life come free to us
Cause we're just under the upper hand
And go mad for a couple grams
And she don't want to go outside, tonight
And in a pipe she flies to the Motherland
Or sells love to another man
It's too cold outside
For angels to fly

Most people just walked on past him, but a few people stayed and listened. Some threw money into the tin placed in front of Castiel's guitar case. Some occasionally swayed to the music.

The worst things in life come free to us
And we're all under the upper hand
Go mad for a couple grams
And we don't want to go outside, tonight
And in a pipe we fly to the Motherland
Or sell love to another man
It's too cold outside
For angels to fly
Angels to fly
To fly, fly
For angels to fly, to fly, to fly
For angels to die

Castiel plucked the final note and bowed his head. The small crowd he had gathered applauded and tossed some cash into his tin before dispersing.

Castiel checked his watch. Shit. It was getting late, and if he didn't return to the Hoover shop, Frank would probably think he was captured by aliens. He bent down to pack up his guitar.

He was distracted by the sound of money clattering into his cup and a man's voice. "Sorry to bother you, but I think that was just fantastic. You have a great voice."

Castiel's gaze traveled up the stranger, from the work boots to the bowlegs, and up past the tight gray shirt to the very handsome face. The stranger ran his hand through his light brown hair. "Can I borrow your guitar?" he asked. Castiel warily stood up and handed the man his instrument. The stranger took it and began to pick at the strings. Soon he was plucking out a tune. He began to softly sing along.

I'm out of touch, I'm out of love
I'll pick you up when you're getting down
And out of all these things I've done, I think I love you better now
I'm out of sight, I'm out of mind
I'll do it all for you in time
And out of these things I've done, I think I love you better now

Castiel joined in, hesitant and quiet.

I'm gonna paint you by numbers and color you in
If things go right we can frame it and put you on a wall
And it's so hard to say it but I've been here before
Now I'll surrender up my heart and swap it for yours

The stranger suddenly stopped playing. "You know that song?"

Castiel nodded. "Of course I know that song. I usually sing Ed Sheeran."

The stranger looked delighted. "Awesome! Do you always sing around here?"

Castiel blushed. "Yeah. I can't get a job singing anywhere else."

"You know," the stranger said. "I think I might be able to get you a gig at the place where I sing. Do you know the Harvelle Roadhouse?"

Castiel shook his head. "No."

"Here, I'll give you the address." The stranger handed Castiel his guitar, then took out a Post-It note and a pen. "Here, I'll give you a table. You can watch me and see if you want to work. I'll make it on the house." He handed the Post-It to Castiel. "Oh, and I almost forgot. My name's Dean Winchester." He stuck out his hand, and Castiel took it. "Castiel Novak."

"Castiel? That's an interesting name," said Dean. His eyes suddenly widened. "But not in a bad way!"

Castiel laughed. "It's okay. I guess I'll see you tomorrow, at the Roadhouse?"

"Sure," Dean replied. "I hope you decide to take the gig. You have an amazing voice." Then he walked away, leaving Castiel wondering if the encounter was real or just a dream.