Dean didn't like these people, but he still labeled them as friends. Ruby was hot, but she was a slutty bitch half of the time. Benny was an asshole and a bully, but he always had smokes. And Zachariah was a rich douchebag who seriously lacked some brains.

They were all leaning on the wall of the empty building across Lawrence High School, smoking together during lunch.

"I'm bored," Benny said, letting out a puff of smoke from his mouth.

"The hell you want me to do about it?" Ruby said.

Benny tossed the cigarette on the ground and stepped on it. "I got an idea."

Ruby snorted. "In your dreams."

"It ain't about you," Benny said, laughing. Zachariah joined in, but Dean tried his best not to listen to their pointless conversation.

"Is this about another prank?" Zachariah wondered, sticking his hands into his jacket pockets.

Benny shook his head, still staring ahead at the campus. "How'd you guys like to start a bet?"

Dean raised an eyebrow. This immediately caught his interest. He didn't like to brag, but he was a pro at all things betting and gambling.

Benny was already looking at him, smirking. "This has everything to do with you, Winchester."

"What are we talking about, exactly?" Dean said, before agreeing to whatever it was Benny wanted to bet about.

"You know that nerdy-as-fuck guy in Math?" Benny said, rubbing his hands together and shivering from the cold.

"Castiel?" Dean said. There were a few people he'd call nerds in that class, but he knew that Benny only ever wanted to mess with Castiel. Dean never understood why. The guy's only fault was being intelligent.

Benny grinned, nodding. "That's right. He's always looking so lonely, ain't he? Doesn't seem to have many friends around."

"Get to the point," Dean groaned, exasperated.

"I bet you a hundred bucks that you can't get him to date you," Benny deadpanned.

Ruby choked on her diet coke. Zachariah looked confused.

"By dating," Dean started, cautiously. "Do you mean going on one date or starting a relationship with him?"

Benny shrugged. "One date, whatever."

"Hold up," Ruby said. "I want in on this, and I'm sure Zach does, too. Let's up this to three-hundred bucks total. Three dates, and you gotta give us all the embarrassing details."

Zachariah nodded in agreement. "Yeah, that dude's probably never gotten laid before. I bet you fifty extra bucks that he sucks at kissing."

Dean considered this bet. He could use three hundred and fifty bucks, and all he had to do was take some guy out on a date. It wasn't like he minded. He was an open bisexual. The tricky thing would be to get Castiel to trust him enough to agree to go out with him. If he was as smart as he appeared in Algebra II, then he would at least suspect something was up.

Dean was, after all, always tailing Benny. And Castiel was Benny's favorite target.

"Well, I do need a new stereo for my Impala," Dean said, stretching his hand out to Benny. "It's on."

Benny smiled, shaking his hand. "It's on, brother."

It was a simple plan, but when it came down to it, things looked more complicated than they initially appeared.

Dean sat at the same table with Benny every day, but today, he waited at Castiel's table, which was at the far corner of the room. Some guy named Chuck was the only one willing to be Castiel's partner. No one else really enjoyed Castiel knowing every answer to every problem the teacher asked, or that he aced all his tests, or that he always had his homework done but wouldn't share the answers.

Castiel was the black sheep of the class.

Benny sat alone, now, looking humorously at Dean. He wanted a show, and Dean was gonna give it to him.

When Chuck walked in, he stood in front of his usual table, glancing at Dean, perplexed. Dean waved casually at him.

"Mind if I sit here today?" Dean said. "You can go make my buddy company over there." Dean tilted his head to Benny, and Chuck looked in his direction. Dean held in a laugh when he saw Chuck swallow nervously.

"I—uh, can take the other seat," Chuck said slowly, pointing at the empty seat besides Dean.

"But where will Castiel sit when he comes in?" Dean said, forming an incredibly cheesy frown. "I really want to talk to him about something important. But don't worry, Benny doesn't bite."

Chuck looked a little scared, and Dean wasn't sure if he feared Dean or Benny more. "Have you ever even spoken to Cas before?"

Dean raised both eyebrows, defiantly. "You're testing my patience, Chuck."

Chuck nodded hurriedly, pacing to the table and tossing his backpack on the floor as he sat down. He looked grim, but Benny was ignoring him, his entire attention focused on Dean.

Castiel entered the classroom, walking down the rows of tables, his eyes set on his feet. He finally looked up when he got behind the table, ready to sit down. He froze before his ass laid on the seat, his blue eyes staring at Dean in complete shock.

"Take a seat," Dean said, winking smoothly.

Castiel's eyes widened and his ass finally fell on the chair. He pulled out his Algebra book, notebook and two perfectly sharpened number-two pencils. It was eerie how meticulous he was, but Dean kinda liked it.

Dean registered Castiel's outfit. He was wearing dark jeans, a fitted blue sweatshirt and gray Toms. Castiel's hair was undone, almost like he just rolled out of bed and didn't bother with brushing it. Dean tried to come up with something flirty to say, something that sounded genuine, and he went with the first thought in his mind.

"Your sweater matches your eyes," Dean blurted out. Castiel looked over at him, blinking.

"Why did you take Chuck's seat?" Castiel muttered, his hands turning into fists on the table.

Dean thought this would be a whole lot easier, but Castiel didn't seem too into him. It's fine, Dean thought. He still hasn't seen the ol' Winchester charm.

Dean scooted his chair closer to Castiel, but the other guy just leaned away. "I thought we could be friends," Dean said. "We've had this class together for so long, and we've seen each other in the hallways since freshman year. I mean, don't you agree with me? We should be friends!"

Castiel squinted, pushing his chair into the table. Dean gave him some space, but kept his easy smile.

Mr. Fitzgerald walked into the classroom, then, carrying his usual briefcase. He probably had their tests graded by now, a test Dean was sure he'd failed.

Shit. "What do you say, Castiel?" Dean pushed, knowing their time to talk was running out. He glanced over at Benny, who looked irritated with him.

Castiel rolled his eyes. Did he seriously roll his eyes—at Dean?

"I don't know who's paying you to say all this, but I don't buy it," Castiel said, sitting straight up in his chair.

Mr. Fitzgerald was already addressing the class about yesterday's assignment, but Dean was not listening. "I'm being serious, man," Dean said, softening his voice. "I want to get to know you better. Why don't we have lunch together today?"

Castiel shushed him because the teacher was now starting the lesson and Dean grew impatient. He pulled out his own notebook, which was filled with senseless scribbles and fragmented lyrics, ripped out a clean page and began writing.

Lunch today?

Dean shoved the note to Castiel, and he spared a quick glance at it. Castiel sighed after a while, and then took the piece of paper and wrote on it. He slid it to the middle of the table for Dean to get it.

Why?

Dean took a deep breath, writing again.

Because I need better friends.

Castiel read the note, and his response came sooner this time.

Where?

Dean smiled to himself, already feeling three-hundred-and-fifty bucks richer as he wrote down the reply.

Steak-n-Shake. On me. I'll drive.

Castiel read the note, and then looked up at Dean, frown creases on his forehead.

Dean shrugged innocently. Castiel wrote a response.

Where will you leave your other buddies?

Benny kept turning back to stare at Dean's table, and it was making Dean a little uncomfortable. Castiel would notice soon enough.

They're a bunch of jerks, we don't need them.

Castiel licked his lips before writing on the note again.

As far as I know, you're also one of them.

Dean nudged Castiel under the table with his foot. Castiel pretended not to feel anything, staring attentively at the teacher who was plotting graphs.

Dude, take a hint. I like you.

When Castiel read the note, a bright shade of red crept up to his cheeks. It was sort of endearing. He didn't write anything down immediately, and he didn't look at Dean at all for at least five minutes. Then, he simply turned with a smile.

Dean smiled back, feeling successful.

When class was over, Castiel rushed outside, leaving the note behind on the table. Dean picked it up, noting the swiftly written phone number underneath their conversation. Castiel was his.

Dean walked with Benny to their next class, handing him the note as evidence.

"I knew you wouldn't disappoint me, brother," Benny said. "I gotta make some copies of this, then I'm gonna frame it."

Dean patted his shoulder. "You better get that money ready. I'm going to start looking for some stereos online."

Benny laughed as they parted ways down different hallways. Dean wondered if he should at least feel a bit remorseful, but all he could think of was that brand new stereo on his beautiful Impala.

When the bell rang, dismissing the students for lunch, Dean texted Castiel to meet him in his car. Everyone knew the gorgeous black classic car in the parking lot belonged to Dean.

Castiel didn't reply, but he showed up a few minutes later. He waved at Dean through the passenger window before climbing in.

"Hey," Dean said, putting his sunglasses on. He looked in the rearview mirror and liked what he saw. Nothing like his favorite leather jacket for a first date.

Castiel cleared his throat as Dean turned on the car, it roared to life. "Hello, Dean."

"We're gonna have a good time…buddy." Dean smiled as he drove them away.

Dean opened the door to Steak-n-Shake and Castiel looked taken aback as they entered. They sat on a booth for two, and Dean stared at Castiel as he looked through the menu.

"Aren't you ordering anything?" Castiel said, eyeing him over the menu.

Dean removed his sunglasses, folding them onto the neck of his shirt. "Of course I am, baby. I'm just enjoying the view." God, that was pathetic and sleazy.

Castiel made a face at Dean, and then rolled his eyes again, as if dismissing his entire behavior. "This is just a pity date, I know."

Dean leaned forward, confused. "What?"

Castiel put the menu down, staring at Dean. "A pity date. Benny's always messing with me so you're taking me out 'cause you feel sorry for me. I get it, I don't mind it. I like free food."

"You really don't trust me?"

"I'd like to say I don't know you, Dean, but I do. Three years together at the same high school lets you learn of even the most insignificant people there. You're just like Benny and his gang of useless friends, though you pretend not to be."

Dean winced at the coldness of Castiel's voice. "Is that really any way to talk to the guy who's paying for your food?"

Castiel sighed. "Guess not. I will take advantage of this situation, though. I want the biggest milkshake and I want a triple-decker, with cheese fries. Do they have onion rings, too?"

"Gold digger already," Dean remarked, leaning back in his seat. "I like it."

Castiel raised his eyebrows animatedly, and Dean laughed.

After they ordered and their food was brought over, Dean tried to move his game up. Castiel was onto him.

"So, Cas—Can I call you Cas?" Castiel nodded, eating a fry. "Great. So, Cas, what do you have planned for the rest of the day?"

"Hmm. Well, after Gym I just have to walk home, maybe do some homework before helping my aunt with dinner."

Dean decided to take a different route. Getting to know his date's family members was always a nice tactic. "You live with your aunt?"

"Yeah, Aunt Anna," Castiel said, looking down at his food. "After my parents died a few years back I had to move in with my aunt. She's nice, but I'm moving out as soon as I turn eighteen."

Dean nodded, listening. "How did your parents die?"

Castiel told him about the tragic night when a burglar snuck into his house to rob, but his parents walked in on him, and he managed to shoot and kill them both while Cas was sleeping upstairs. Dean finally started feeling guilty about doing this to him, especially because Cas didn't completely mistrust him, but he pushed the feeling aside.

"Hey," Dean said, placing a hand on top of Castiel's. "I'm really sorry about your parents." Dean cleared his throat and removed his hand before going on, "If it's any consolation, my dad passed away last year. He had a clogged artery and died before getting to the hospital."

Dean looked away. He never talked about John. Ever. To anyone. And to spill his life story to a guy he was just using was the last thing he wanted. But somehow, he felt he owed it to Castiel to share something about his life as well.

"That must have been hard for you," Castiel muttered, regarding Dean with a soft look on his eyes. "I'm sorry, too."

Dean finished his milkshake rather than speaking more on the subject. Cas was already done with his load of food, and Dean checked the time on his phone. They had ten minutes to get to class.

"We should head back," Castiel said, getting up. Dean silently agreed, paying the check and holding the door for Cas on the way out.

Dean decided to go all out and opened the car door for Cas, too. Cas gave him a funny look as he climbed in.

Dean got behind the wheel and turned on the engine. Cas messed with the static-y radio on the dash, and Dean felt a little guilty again.

"Your stereo stinks," Cas complained, turning it off, again.

"Tell me about it." But you're going to fix that problem, Cas, so thanks, ahead of time.

Castiel started humming a song on the drive back to school, though Dean didn't recognize the melody. But then, as Cas got more into it, air-drumming and everything, a few lyrics slipped out in a velvet voice. "And now's the time, the time is now, to sing my song…"

Dean jerked to a stop a block away from school. He turned to Cas, shocked and astounded. "You're singing a Zeppelin song? You're singing Ramble On?"

Castiel looked scared for a fleeting second, and then he scratched his head, confused. "Does my singing bother you? No one ever comments on it, so."

"Dude," Dean said, excitedly. "Dude, Ramble On's my favorite song! I can't believe you listen to Zeppelin. Where the hell have you been hiding all these years?"

A car honked behind Dean, and Dean finally pulled into the school parking lot, getting in his previous spot and cutting the engine. Castiel checked his watch and Dean knew it was time for class, but suddenly he was too excited to let Cas leave.

"You have any plans for tonight?" Dean said, staring hopefully into Castiel's blue eyes, which completely matched his sweater.

Castiel shook his head. "You can text or call me if you want to hang out, but I have to get to class, now. Bye, Dean."

"Bye," Dean whispered, watching Castiel run out of the car and speed through the parking lot into the building.