A/N This is probably just going to be a short 3 or 4 part story. Loosely based off the song Falling In Love At A Coffee Shop by Landon Pigg. Well, Enjoy, and Reviews are appreciated.

"Just a regular coffee, thanks" Castiel said to the employee at the front desk. She nodded and started up the coffee machine. He waited in silence for it to finish brewing. The girl poured it into a cup, "Cream and sugar?" She asked.
"No thank you. I like it strong." He smiled. The girl put the lid on the cup and slid it over to Castiel. He gripped it and got out of the way of the line. He stood at the edge of the counter, and looked for a place to sit. Sadly, all the tables were taken. Castiel swore silently to himself, he was expecting a date today, and there were no seats for them to sit at. The only available seat was across from a man with long brown hair and what seemed like an extra extra large drink. He wondered if the table with the lonely man was his date. That was the downside to going on a blind date, you never know what the person is supposed to look like. That always made it hard to find them.
Castiel slowly walked over to the man, "Excuse me? May I sit here?" He said quietly. He didn't want to bother anyone else in the room. The man looked up from his phone, "Yeah, sure."
"So..are you Dean Winchester? I was expecting him here today. I'm Castiel, by the way." Castiel asked as he pulled the chair facing him and sat in it. He placed his coffee on the table.
"No...that's actually my brother..." He answered.
"Oh...I see. Do you know where he may be?"
"No...He had a date today."
"I'm his date..."
The man tilted his head, "Really? Because he picked her up today...Are you sure it was supposed to be him?
Castiel swore. He knew his brother would do this to him. "My brother, Gabriel, told me that Dean was to meet me here at this time, at this place. It's so much like him to do this to me. He loves to play pranks on me. "
"Gabriel is your brother?!" The man's eyes widened.
"Sadly, yes. Also, What is your name? I never caught it." Castiel took a sip of his coffee.
"Sam. That is weird though. Gabriel was my roommate in college. He told me he was setting me up on a blind date with his sister Anna..." He pulled his long, shoulder length, brown hair behind his ear. Castiel found his hair attractive. He usually enjoyed shorter hair on men, but the way Sam's hair casually flowed, it looked great. The way he pulled it behind his ears, made him seem almost...beautiful. Long hair usually looked girly on men, but the long hair didn't have that effect on him. Castiel's heart sunk when he heard the word sister. That most likely meant he was straight. Castiel knew then that he wouldn't be going on any dates today, the most he would get was a chat with his supposed "date's" brother. He would just have to suck it up.
"I think Gabriel is trying to tell us something." Sam smiled. He took a sip of his drink and took a bite of his muffin.
"How? All he told us was the wrong dates to meet." Castiel's hands were starting to get cold so he wrapped his fingers around the hot cup of coffee.
"Well, that of course, and maybe he was trying to get us together. Why else would he send us both here on the same date, telling us he was setting us up with someone." Sam chuckled.
Castiel shrugged. It was quiet for a while, and both men awkwardly sipped their coffees without saying a word.
"So...since this is a 'Date'" He made quotation marks with his fingers, "I want to know a little more about you. Like, how old are you?"
"Well...I'll be 29 in a couple of weeks, but 28. You?" Castiel rattled his cup a little bit, and realized it was already starting to empty. He would have to go up later and get more.
"Oh. I'm 23, I just graduated last year."
"That's nice. What major?"
"Law. My brother thinks it's silly. He thinks that I should join him in our family business. I always tried to tell him and my dad that I'm not interested in being a mechanic. It was never my forte."
"I see. My brother took law, that's why he was your roommate. He went to college later in life than usual. I majored in English when I went to college. That's why I'm a teacher."
"Teacher. That's hot." Castiel couldn't tell if Sam was being sarcastic or serious.
"Hey, I ran out of coffee. I can see you are also running out. You wouldn't mind getting me some too? It's just a regular, no creamer or sugar." Castiel asked.
"Yeah, sure." Sam picked up their cups and walked over to the counter. Castiel couldn't help but dart his eyes at Sam's ass quickly. As soon as he did, he shot them back to his fingers, hoping no one noticed.
Sam walked back, and handed Castiel his coffee, "So, where do you teach?" He asked calmly while sitting in his seat.
"I currently teach freshmen in high school." Castiel took a sip, not caring that the coffee burned his tongue.
"Ouch. That must be rough. They must be a hassle. My freshman class were all complete assholes."
"They aren't that bad. Yes, some of them can be irritating. However, I love teaching. It's worth it to see them achieve goals. Even if some of them call me rude names. So how about you? Do you have a job yet?" He had to ask. Castiel knew Sam just graduated, but he was extremely curious.
"No, not yet. I've applied for a few job at law firms, but none of them got back to me yet. But I'm hoping one of them will." He looked at his fingers. It was almost as if he was ashamed. He almost looked like a puppy when he did that. Castiel couldn't help but find that adorable. It was amazing how someone could change their expression so fast like he could.
"Well, I hope you can get the job you want. It took me awhile to get my current job. You'll get it sooner or later."
"Thanks, Cas. You don't mind if I call you Cas? It's just a lot easier than calling you Castiel."
"That's fine. " Castiel answered. His brother called him Cassie, which annoyed the shit out of him. Basically anything that Gabriel did, annoyed Castiel. He liked the nickname Cas. It was short and sweet, it wasn't too annoying, and it wasn't sophisticated. It was something only his close friends could call him, but he was letting Sam slide with that.
The two chatted for awhile, while they refilled their cups multiple times. Castiel learned a lot about his date. Sam was born in Lawrence, Kansas. His mother died when he was only 6 months old, and his father owned a mechanic shop. His father also died a year ago, and Sam still lived with his brother. He also learned about a few experiences in college, and some of his childhood memories.
"So...what is your brother like? Am I missing out?" Castiel asked. He was curious as to what Dean was like.
"He's a great guy. He may seem rude to people who barely know him, but after awhile, he can be really sweet. He's always been there for me, no matter how bad the situation. He can be annoying sometimes, but I tend to overlook that. As a lover, he's terrible. He goes through girls like kleenex. He's better as a friend than a boyfriend. So how about your sister?"
"Wow. Then I'm glad I have you as my date. My sister is actually married." Castiel smiled lightly.
"Well, I'm glad I have you as my date. I wouldn't want to go on a date with a married woman. And yes, I am bisexual. I don't think gender should matter."
"I feel the same way. Though I have a preference for men."
"I'm sorry to ask, but what time is it?
"It's around 6." Castiel looked at his watch.
"Wow. We've been here for over three hours. So, do you want to go see a movie?" Sam asked. It didn't seem like a bad idea.
"That would be pleasant."
And it was. Castiel really enjoyed it. He barely went to the movies, since he rarely went on dates. It was very nice with Sam. He paid attention to both the movie, and to Castiel. In the middle, he grabbed Castiel's hand. He loved how large Sam's hands were compared to his. He was able to trace them, and they held hands throughout the whole movie.
Since Sam's brother drove him to the coffee shop, Castiel drove Sam home. He pulled into the driveway, and the two of them walked out. They walked to the front door, and Sam unlocked the door. "So...I had a great time today. You think we could do this again?" Sam asked.
"Yes. I would love that. How about next friday? I can make us dinner." Castiel propositioned. Sam nodded in approval.
"So...I have to go inside. I don't want Dean to start freaking out. He can be kind of over-protective sometimes. It's not like I'm 16 anymore. But what are you going to do. He'll eventually get an actual girlfriend and move out. Or I'll do that. Whatever comes first." He winked.
"I've lived on my own for a while now. My brothers kicked me out when I finished college. I'm fine living by myself, it's quiet. My brothers were always extremely loud when I lived there, so I was more than happy to finally leave them. I love my brothers, but enough was enough."
"Wow. I've always just had the one brother. We've lived together our whole lives, so I've gotten used to him. But anyway, I really need to go."
"Oh...Well, goodbye!"
"See ya friday. " Sam walked halfway through the door. He then pivoted, "You know what?" He grabbed Castiel's cheeks, and pulled him into a kiss. Castiel put his hand behind Sam's neck and softly kissed him back. They kissed for a couple minutes, then Sam pulled away slowly.
"You can't end a date without a kiss. I'll definitely be seeing you friday. Good Night." Sam walked into his house and closed the door. Castiel stood there, starstruck. He couldn't believe his luck.
All of this happened because his brother played a silly prank on him. He needed to thank him later.