39 Blind Dates (Destiel AU)

Chapter 1

Dean didn't know what to expect. He had recently come out as bisexual, and since than had been single, no matter how many gay bars -or regular bars, for that matter- he visited, yet there were no keepers.

Sure, there were people looking for a one night stand, but he wasn't really interested in that. He was ready to settle down, perhaps find someone who didn't always have sex on their mind. He instead wanted cuddle and watch lame shows together, debating on whether they should watch the next episode or finally turn in for the night.

Don't get him wrong, though. He would like sex, but in a more loving way, rather than drunken passion.

So here he was, waiting for the fourth blind date that his best friend, Charlie had set him up on.

Frankly, he was terrified. He hadn't dated anyone in a little over a year, and he really didn't remember his college days as a player, able to make any girl fall in love with him, back when he was denying his interest in men.

Finally, his date arrived. It was a male; tall with shaggy blonde hair, wearing a plain white t-shirt accompanied by dark blue jeans. He looked around, quietly saying Dean's name, scanning the room for any sign of his new date that would raise his hand. Dean got up out of the chair and strode towards him, and hesitantly asked, "Jake?"

"Yeah, that's me," Jake replied, holding out his hand. Dean took it and his lips tugged up, attempting to smile brightly.

"Um, we're sitting over there," Dean said, pointing to the back. Jake nodded and together they headed over there, and they sit in tense silence until a waitress comes to get their order.

"I'll have a burger," Dean said, then looking expectantly at Jake, waiting for him to make an order.

"I'll have the same."

"Would you like anything to drink besides water?" the waitress asked.

"No thank you," they said in unison.

The waitress left, and they were once again surrounded by silence, until Dean had finally decided to break the ice.

"So what do you do?" Dean asked, slightly tipping his head to the side. He was already guessing what Jake would say, but he really didn't have an idea that actually stuck.

"I'm pursuing architecture," he answered. "What do you do?"

"Oh, I'm an artist. I paint, draw, sketch, also dabble in photography, but I work at a coffee shop to earn a little extra money," Dean replied. Jake raised his eyebrows and nodded, and Dean could have sworn that Jake perked up at that bit.

Into artsy-fartsy people, eh? Dean thought, smirking. They talked about their interests and just random things in general, trying to get an idea of each other, calculating their compatibility.

When they received the check after they finished their meal, they agreed to split it, and they shook hands, deciding to exchange numbers, but Dean already could tell it wouldn't work.

Jack was a nice guy and all, but there was something about him that made Dean feel slightly uncomfortable and on edge.

Leaving the restaurant, Dean called Charlie to let her know how it went.

"Hey, Charles," Dean said, getting into his beloved '67 Chevy Impala.

"How'd it go?" She asked excitedly, and Dean could imagine her bouncing around their shared apartment, squeaking so loud that they would get a sharp knocking on the walls.

"It was okay, but I don't think it'll work out," Dean replied, and now he imagined her deflating, the squeaks stopping abruptly much to the neighbor's delight.

"How come?" Charlie questioned, sounding just as disappointed as Dean would have imagined.

"I don't know, it just didn't click. Sorry, Charlie," Dean said, feeling bad for Charlie, who had tried hard to get Dean a partner.

"Well, onward and upward!" Charlie said, trying to sound cheerful. Dean smiled sadly and said goodbye, so he could get home safely.

Getting home, he was bombarded by hugs and apologies, and Dean accepted them, saying it wasn't Charlie's fault his love life was a complete fail.

They bundled in for the night, deciding to watch Star Wars for what seemed like the millionth time, but neither of them minded. They always made stupid commentary, and when a famous line came on, they looked at each other and mouthed it, then returned to the movie, chuckling a bit.

Before they went to bed, Dean texted Sam, who was now in college, studying to become a lawyer. To his surprise, Sam responded, then Dean realized that Sam probably had to pull an all-nighter. He told Sam that he was going to bed, then plunked onto his bed, falling asleep after brushing his teeth and changing into sweatpants.

The next morning, Dean was awakened to the unpleasant commotion of his alarm clock emitted, and he grudgingly got out of bed, getting ready for work. Charlie was already gone, probably heading out to get a coffee before she heads to work. It had become a habit for her in the past month, though Dean couldn't imagine getting up even earlier than he already did.

He got ready for work and shoveled down cereal before he walked to the local coffee shop only a couple blocks from the apartment that they lived in.

While working his shift, he kept sneaking in secret phone checks, texting Sam and Charlie about Batman in a group chat, until he heard someone clearing their throat. He jerked his head, seeing a gorgeous man standing before him.

He had raven black hair that looked quite messy, as if he had just woken up. He was wearing a long, a far too big beige trench coat with a blue tie, and a button up white shirt. When he made eye contact with him, he saw that the man had bright blue eyes that perfectly matched his tie, and Dean was taken back by the intensity.

"Hello?" The man asked, tilting his head to the side, reminding Dean of himself and jerking himself out of trance those eyes had put him under.

"Oh, um, sorry. What did you want?" Dean asked, his words fumbling and falling over each other.

"I just wanted an iced tea," the man said. Dean nodded and picked up a plastic cup, scribbling over it.

"What name should I put it under?" he asked.

"Castiel." Dean raised his eyebrows, scribbling the name down. He gave Castiel his best smile. "Alright, Castiel, your order will be ready soon."

Castiel nodded his thanks, and sat in the corner, staring out the window, presumably waiting for his drink.

When Castiel's drink was ready, Dean called his name out and waited until he came over to retrieve his drink so he could talk to Castiel.

Castiel approached again, and saw Dean looking his way.

"Hello again," Castiel said, grabbing his drink and a straw.

"Hello," Dean said, before adding, "You should come here more often."

"Why come?" he asked, tilting his head again, making Dean's heart flutter more than it ever had when he was on a blind date.

"Because I liked meeting you," Dean said simply, and Castiel's face took on a look of surprise.

"Perhaps, but I'm unable to for a couple of days. I have work especially early."

Dean nodded, a little disappointed, but was glad there was a possibility. "Well, I'll see you then. My name's Dean, by the way."

"Well, Dean, until next time," Castiel said, giving a little wave and started heading out the door.

"Until next time," Dean murmured, then returned to take the order of an elderly couple who had recently started coming here daily.

A/N

What did you think of the first chapter of my Destiel AU? I'm really proud of it, and I think it's coming along nicely. Please vote and comment if you enjoyed it!

Hope you enjoy, my lovelies.

Inu