There were many things Dean regretted in his life- not getting Sam that Harry Potter book for his tenth birthday, not turning that one science project in on time- but his latest regret was setting his morning alarm for 7 in the morning after staying up until 1 am.

When the alarm on his phone went off, it tore Dean out of his tender dream and into the harsh reality of morning. He fumbled for his phone, muttering to himself as his fingers finally clasped onto the small device and he frantically turned the wailing alarm off. With a huff, he rolled onto his back, stared at his ceiling and sighed.

His room was yet to be fully decorated- he surprisingly still had some unpacking to do- but he had a desk, a computer and the walls were painted. The paint can had said mahogany on it, but Dean couldn't tell if the can had been lying or not, as his room was still solid gray to him. Nevertheless, he just assumed it was mahogany and had painted his room with it.

Next door to him, Dean could hear the familiar sounds of Sam getting ready- the shuffle of his closet doors, the crumpling of clothes onto the floor, and the shuffling of shoes. Dean didn't have to guess Sam's next move, though; in a moment, Dean's door was swung open by a way-too-eager Sam.

"Good morning Dean! It's time to wake up, school starts at 8:30!"

"Yeah, yeah, I know." Dean groaned, rolling onto his belly before lifting his hand to flip Sam off. Sam cried out a familiar "Jerk!" before he closed Dean's door, drowning out the "Bitch!" that followed.

With a huff, Dean rolled over and closed his eyes, hoping to get some sleep in. The world wasn't that kind, though, and Bobby was knocking on Dean's door in minutes.

"Dean! Get your butt up, you have school today!"

Dean groaned again in dismay, but ultimately sat up when Bobby nearly kicked his door in.

"Alright! Alright! I'm up!" Dean cried, holding his hands up in surrender. Bobby gave a small huff before shoving a shirt in Dean's face.

"Here. Wear this."

It was Dean's favorite plaid shirt, one that Bobby had washed specifically so Dean could wear it today.

"Thanks Bobby."

Bobby shook his hand. "Ah, don't thank me boy. Put that on and get ready so you aren't late for your first day. You still gotta get your schedule, don't forget."

Dean nodded. "Yeah, I know. First place Sam and I'll head will be the main office, if we can find it."

"I'm sure someone'll point you in the right direction."

Dean nodded, and Bobby closed the door behind him, leaving Dean to get ready for the day, which he did. Dean pulled on the plaid shirt and put a jacket on over it- his hand-me-down leather jacket, in fact, which was one of the only positive memories he had of his father.

After adorning a pair of jeans and his regular, everyday shoes, Dean finally emerged from his bedroom at 7:35 am.

Sam was already downstairs and eating breakfast- buttermilk waffles with syrup, expertly made by Bobby.

When Dean reached the table, he was greeted by Arizona- Sam's dog, whom they had adopted two weeks prior. She greeted Dean with a playful bark, and he gave her a quick pat on the head before sitting down. As soon as he did sit down, Bobby slid a plate of waffles his way, and Dean dug into them almost immediately.

As he savored the delicious taste of fluffy buttermilk waffles and homemade syrup, Sam finished his own plate and put it into the sink with a clatter before rinsing it off with water. Sam then got a drink and downed his morning pill- a pill prescribed to both Sam and Dean, to combat anxiety and stress. When Sam downed his, he took Dean's pill into his hand and handed it to Dean, who downed it as soon as he finished eating his own plate of waffles.

Bobby grabbed Dean's empty glass of water as soon as he was done with it, but not before he turned to Dean. "Hey, Dean, don't forget that you have a therapy appointment after school."

"Yeah, I haven't forgotten. What time will it be, 4 or 4:30?"

"4:30."

"I won't miss it, Bobby."

"You better not."

Dean let out a laugh as he shoveled another forkful of waffle into his mouth. He finished his plate in minutes, and rinsed his plate off in the sink before grabbing his backpack. By that time, Sam was already ready, his backpack on his back, stuffed full of binders and notebooks and a Harry Potter themed pencil pouch. He was sitting by the front door, his hands dug into Arizona's fur, petting her eagerly as he cooed at her.

"You ready to go?" Dean asked, tilting his head as he grabbed his Led Zeppelin themed backpack.

Sam paused petting Arizona and nodded eagerly, clasping the straps of his backpack, which, like his pencil pouch, was Harry Potter themed. "Yep! I'm ready!"

"Alright then. Go out to the car, I'll be out in a second."

Sam bid Arizona and Bobby goodbye, then ran out of the house and towards the car, the '67 Impala the boys had repossessed from their father two years prior. He stood on the passengers side, waiting patiently as Dean opened the front door of the house and walked out. Sam hopped in as soon as Dean unlocked the car, setting his backpack and lunch box at his feet.

"Alright. You ready for your first day of high school?" Questioned Dean, tapping his fingers on the steering wheel. Sam nodded eagerly, sitting up a little straighter as he stared at the house through the windshield.

"Yep!"

Dean's lips curved up into a smile, dousing his face in warmth as he faced the windshield. "Alright. Let's go."

Dean dug the keys into the ignition, laughing when the car erupted to life with a familiar roar. It softened to a purr, one that was very comforting to both brothers.

Dean eased the car out of the driveway, and once he rolled back onto the road, he drove off towards the school, leaving the house behind.

~~~~~

Cas woke up the morning of the first day of school to a face full of fur. Spluttering, he almost immediately sat up, scaring his cat right off of his chest and sending her bounding across the room.

"Gemini!" He cried out, eyes landing on the black and white ragamuffin cat that was now sitting next to his door, pawing at it helplessly. "How many times have I told you to not wake me up like that?"

Cas's other cat, a bombay cat named Nox, meowed in disapproval at Gemini. Cas just sighed and tore his bedsheets off of himself, sitting up on his dark colored bed. He walked over and picked Gemini up, startling a mrr from her as he set her back down on his bed.

Cas walked over to his closet, and out of it came his usual trench coat. He also pulled on a Hufflepuff shirt, a pair of jeans and some (from what he had been told) dark gray sneakers. He paused in front of the mirror, patting his hair to make sure that it was somewhat neat. (His hair was so messy that he'd long given up on making it be completely and utterly neat)

The first thing he heard after opening his door was the sound of Lucifer yelling at Gabriel to get up. Given how common the sound was, Cas just shrugged it off and went downstairs, Nox and Gemini following closely behind. That was until two of the other cats of the house, Quinn and Coffee, came walking out towards Nox and Gemini, and the two cats paused to meow at them.

Cas went downstairs regardless, walking up to the kitchen bar, where Raphael, Balthazar and Anael were sitting, eating breakfast.

"Cas! Hey, there you are. Mom made waffles for breakfast." Balthazar exclaimed, pushing a plate of waffles towards Cas as he sat down. Cas took the plate, drizzled some syrup over it and took a bite.

"Is Lucifer gonna drive us to school?" Inquired Cas as he stuffed a forkful of waffles into his mouth.

"Lucifer will drive half of us and Gabriel will drive the other half. So we get to choose whose car we go in." Anael explained, setting down her empty milk glass. "I'm going with Lucifer."

"I'm going with Gabriel." Said Balthazar, setting down his fork onto an empty plate. "I don't really wanna go with either of them, but Gabriel has better taste in music. All Lucifer listens to is hard rock."

Cas set his own fork down for a brief moment. "I'll go with Gabriel as well. He has Imagine Dragons in his playlist."

"Rock haters." Muttered Anael, poking Balthazar's arm. He swatted at her hand and she laughed, pulling her hand away.

"Good morning." Came a voice, belonging to none other than Samandriel. He was still dressed in yesterday's clothes, but his hair was brushed neatly and he was holding a shirt in his hand. "What's for breakfast?"

Balthazar grabbed Cas's plate and held it up. "Buttermilk waffles with syrup."

As Cas snatched his plate back, Samandriel nodded and left the room to go change before he ate.

Gabriel was the next person downstairs. His hair was a mess and his eyes were tired, and on his face rested an irritated expression, clearly from Lucifer banging his fists against Gabriel's door. Apparently Gabriel had gotten up after Lucifer threatened to replace all his candy with fruit.

Gabriel took his own plate of waffles, pausing as his dog Hershey ran down the stairs to follow him. He gave Hershey a pat on the head before he sat down and began to pour syrup on his waffles.

As Gabriel nearly drowned his pancakes in syrup, Balthazar clicked his tongue in disgust. Unfortunately for him, Gabriel heard the noise, and shot a glare at Balthazar as he tucked the syrup bottle away.

"I could let Lucifer drive you, if you're so against my syrup methods." Gabriel remarked, taking a forkful of waffle.

"No, don't." Balthazar sighed, taking his empty plate to the sink. "I'll ride with you."

Gabriel tossed his head and downed another forkful of waffle.

Samandriel was the next person to enter the kitchen that morning for breakfast, having changed into some good clothes. He was now dressed in his typical attire- a striped shirt that Chuck had said was white and red, a pair of jeans and some dark shoes which Chuck had also said were dark red. He grabbed a plate of waffles and drizzled quite a bit of syrup onto them before taking a forkful of waffle.

"Hey guys," Cried Becky as she walked downstairs, "School starts in one hour. You should probably head out in the next fifteen minutes."

"We will!" Cried Anael, dumping her plate into the sink. She rinsed it off with water and then left it as she ran upstairs to get properly dressed.

Lucifer finally came downstairs just moments after Anael ran upstairs, and he was followed by Hannah and Anna, both of whom were dressed and ready to go. As the three descended the stairs, Hannah grabbed Coffee, who was sitting on the fourth stair, and took her back to her room to put her up. Anna grabbed her own cat, Quinn, and put her up as well.

As soon as Cas finished off his own plate of waffles, he discarded it in the sink, gave a pat to Hershey and went to put Gemini and Nox up. It was a bit of a struggle to get Gemini up, but Nox came willingly and perched herself on the top of the cat tower as Cas closed the door.

By the time all the pets were put up, both Gabriel and Samandriel had finished their breakfast. As they put their plates in the sink, Gabriel grabbed his car keys right as Lucifer walked out the door with Hannah and Anael.

"You guys ready?" Questioned Gabriel as he opened the front door for his siblings. Cas, Balthazar and Samandriel all shook their heads, and Gabriel laughed. "Yeah, me neither. At least this is my last year."

The four brothers climbed into Gabriel's car, and Gabriel immediately plugged his phone in and began playing his usual playlist. The first song to come on was Pump It by The Black Eyed Peas, and Gabriel turned the music up as he pulled out of the driveway. Balthazar slowly began to lipsync to the song as the car rolled out of the driveway and down the road, towards the school. The ride was a mere ten minutes, during which two Elle King songs ("It's a guilty pleasure," said Gabriel) and an Imagine Dragons song played through Gabriel's playlist. By the time they reached the school, the parking lot was already half full. Gabriel parked in the seniors lot, and Cas, Balthazar and Samandriel hopped out of the car almost immediately.

"You guys got your schedules?" When everyone nodded, Gabriel held his own up. "I got English 4 first, what about you guys?"

"I have creative writing first." Cas murmured in reply, glancing at his schedule.

Balthazar scanned an eye over his own schedule. "Spanish 2 is first for me. Ha! I got Mr. Harrison!"

Samandriel tilted his head. "Mr. Harrison?"

"He's the most entertaining of all the spanish teachers." Balthazar explained. "What's your first class, Alfie?"

"English 1 honors with a Mr. Lester."

"Mr. Lester? Lucky, he's one of the nicest teachers. I got stuck with the mean English teacher my first year." Gabriel remarked. "What lunch periods do you all have?"

Cas raised his schedule up. "6th for me. Just like last year."

"5th for me," Replied Balthazar, as he shot a glance at Samandriel's schedule, "and 4th for Alfie."

"Alright. I'll see Cas in 6th lunch. And you two," Gabriel turned to face Samandriel and Balthazar, "I'll meet you two back at my car after school. Alright, let's have a halfway decent first day."

~~~~~

"So, what class do you have first?" Inquired Dean, as the lady in the office handed both brothers their schedules.

"Geometry honors."

Dean shook his head. "I've never understood why anyone would put math first. I got US History first, though. Thankfully."

"With what teacher?"

"Ms. Rankin."

"Ms. Rankin's class is in the 300 hall." Explained the office lady. "And the math classes are all upstairs, furthest hall."

Sam nodded in understanding and heaved his backpack up. "Thank you. Have a good day Dean."

And with that, Sam walked off to his first class, Dean close in tow. The two brothers split when Sam had to go upstairs, so Dean continued going forward until he reached the 300 hall.
"327, 327.... ah! There it is." Exclaimed Dean aloud as he spotted his first class.
When he walked in, he couldn't help but sigh in awe at the classroom. It was fully decorated- fairy lights strung along the board, curtains over the windows and posters over the walls. As he walked in, he was approached by the teacher- a relatively pretty woman who was holding some papers. She held one up and glanced at Dean.

"Name?"

"Dean Winchester."

"Ah, Mr. Winchester. You're in this seat," she pointed towards a seat in the third row, "Right next to Ms. Bradbury. I trust that you two will get along."

Dean nodded, and he went to go sit down in his seat. Whoever was supposed to be sitting next to him wasn't yet there, so he set his stuff down and messed around on his phone until the first bell rang. Kids began to trickle into the room, and three minutes before the second bell rang to signal the start of first period, a girl ran into the room and sat next to Dean, setting her stuff down with a huff.

The girl, who Dean supposed was the 'Ms. Bradbury' the teacher had mentioned, had long, somewhat dark colored hair and was wearing a Star Wars shirt. It didn't take her long to notice Dean sitting next to her, and she immediately stuck her hand out.

"I don't think I've ever seen you, so you must be new here. Charlie Bradbury."

Dean took her hand and shook it. "Dean Winchester."

"Winchester? Like the Winchester Mystery House in California?"

"Yeah."

"Awesome. I've been there- it's really cool." Her eyes glanced down to Dean's backpack, which caught her eye. "Led Zeppelin fan?"

Dean nodded. "Yeah. I love their music."

"I do too." Charlie said with a laugh. "My mom, she hates Led Zeppelin. She always complains if I play them in my car. Of course, she doesn't even have to go in my car since she has her own, but I guess she likes to judge my music taste." 

Dean laughed. "Yeah, everyone's a critic."

Charlie pursed her lips and nodded in agreement. "You can say that again."

The second bell rang loudly, and the teacher took the opportunity to close the door.

"Alright, good morning everyone. I'm Ms. Rankin, and I'll be teaching you World History Honors. Since today is the first day, I'll just read the class rules and hand out a get-to-know-me sheet."

The teacher then pulled up a powerpoint and explained all her class rules- and thankfully, there weren't that many. Dean was hoping he wouldn't get any strict teachers.

After the rules came the first activity of the year, a get-to-know-you assignment. It was just a simple sheet where you fill stuff out about yourself, so Dean finished it with ease.

As soon as he finished though, he spotted Charlie trying to glance at his paper.

"You want to trade papers?" He asked, holding his up.

"Oh, I was just wondering what you put as your favorite show." She replied, "I put Sherlock down as mine."

"American Horror Story for me," Dean held up his paper so that Charlie could clearly see it, "But I've been meaning to watch Sherlock. I just got Netflix, so I should be able to watch it on there."

Charlie held hers up to show Dean. "I also like American Horror Story. Favorite season?"

"So far, Asylum. But Hotel is my second favorite."

"Freak Show for me," Charlie put her paper down and zipped her Doctor Who pencil pouch up, "But Asylum is a close second."

"Freak Show scared the living daylights out of my brother. Or at least that clown Twisty did."

Charlie nodded. "I don't blame your brother. Twisty was really scary."

The bell ending second period rang not too long after Dean finished his paper, so he gave it to the teacher, bid Charlie goodbye and went off to his second period- Spanish 2. Spanish wasn't too eventful- Dean had apparently gotten the most entertaining Spanish teacher, Mr. Harrison, who gave them all an eager introduction and passed out a little sheet of paper to describe what the course would entail.

His third period was Math with a teacher named Mr. Saunders, who was also pretty entertaining. Mr. Saunders had started off the class pointing his pointer finger at a kid who had walked in tapping away at his phone, then ended the class with a whoop.

His fourth period was Chemistry, which wasn't all that entertaining. The teacher, Ms. MacLeod, spent the entire class talking about what they would do in Chemistry. Dean also happened to spot a kid in the back of the class who was wearing a trenchcoat, which he thought was an odd choice of clothing, but nothing else really happened. It was his fifth period that became entertaining- when he saw both his brother and Charlie in the class. Sam was sitting at a table towards the back, and Charlie was sitting at a different table- but she soon moved tables when she spotted Dean in the room.

"Charlie! Hey, this is my brother, Sam. Sam, this is Charlie, who I met this morning."

Charlie immediately held her hand out. "Hello Sam! It's nice to meet you."

Sam held out his own hand and took Charlie's hand. "It's nice to meet you too, Charlie."

The bell rang right after that, and the art teacher stood in front of the class and began to talk. She had them do a simple thing- draw a sketch of themselves and personalize it by adding little symbols of things they liked. She handed out colored pencils, and although neither Sam, Dean nor Charlie could tell what color they were by looking at them, they used the pencils nonetheless by reading the color from the side.

The three of them all happened to have lunch after art class, but Charlie took a different route than the two brothers, so they didn't realize it at first. By the time they got to the cafeteria, it was halfway full, with kids pouring in. Sam immediately pointed out a table near the entrance, an empty table, so he and Dean quickly took it and sat down. They both unpacked the lunches Bobby had fixed for them- spaghetti in a thermos, some yogurt and a brownie- and dug in.

"How were your first five classes?" Dean inquired, taking out a plastic spoon to eat his spaghetti with.

"They were alright. My geometry teacher is fine, my law studies teacher is british, I believe. Oh, my french one teacher is also named Sam, and my culinary teacher was pretty nice. She just handed out cookies to everyone in the class and introduced herself." Sam took the brownie out of his lunchbox and handed it to Dean. "No colors yet, though."

Dean stuffed a forkful of spaghetti into his mouth and nearly choked trying to answer. "Well, only like ten percent of people meet their soulmates in highschool, remember? And it's usually in their last two years, not really first year. But hey, don't fret. You'll find your soulmate one day. Though I still don't understand why you want to find them so badly."

"Because, Dean," Sam explained, taking a bite of his spaghetti, "Your soulmate is supposed to be your partner for life. You know, the best friend and lover who loves you for who you are, not for your past or what you've done. And soulmates are supposed to bring you lots of happiness. Isn't it normal to want happiness?"

Dean paused, twirling his fork around in his thermos. "Yeah, it is. I guess I just don't really want to find my soulmate too early. I want to live a little before I'm tied down to one person."

"You say that as though having a soulmate is like being in a jail cell."

"Yeah, well, in some ways it is and in some ways it isn't. I just want to live while I have the chance. Be my own person, experience things that I can't experience with another person at my side."

Sam just shook his head and continued to eat. 'Whatever you say, Dean."

Whoo, almost 4k words for the first chapter? You betcha!
So I meant to upload this later this week, but it's past midnight and I figured eh, why not? So here ya go. Also, all of the teachers (except one) are named after YouTubers (Phil Lester, for example) or my friends (the French teacher after my French friend Sam, for example)
I should hopefully (but I cannot guarantee) upload a new chapter once every two weeks or so. Also, I do recommend reading my other high school au story as well! I'm actually taking quite a few ideas from that story to put in here (cuz I'm lazy and I love recycling old ideas). Anyways, hope ya enjoy the chapter! Second chapter is currently being written and should be up around June 25th-30th!
~ Liz