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Life's Lessons

Summary:

Y/N Y/L/N moves to Lawrence, Kansas to start her life afresh, where she’s hired as the English teacher at the junior high school. Things are going as they would on moving day in a new town, until she meets her neighbor, Dean Winchester. She wasn’t expecting him to be everything she could possibly want. She certainly wasn’t expecting to fall for him, as they get to know each other. He was in a relationship; he had a son, even if he wasn’t actually his. A son who’s in her 8th grade class.

Dean and Y/N can’t deny their obvious feelings for each other. Dean knows that he has to break it off with Lisa, but it’s not that easy, having been together for so long. Will he be able to do it before it’s too late and Y/N moves on with her life?

(Warnings for individual chapters in notes, as well).

Notes:

This series means a lot to me and I hope you all enjoy it! :)

Warnings: some swearing, first day of work nerves, Dean being cute (yes, that’s a warning lol)

(See the end of the work for more notes.)

Chapter 1: A Lesson in Settling In

Chapter Text


Y/N leaned against her car, a content smile on her face as she looked up at the house that she was about to call her new home.

 

The house was clean white, with a grey tiled roof. White wood railings encased the front porch, that had a porch swing in front of one of the windows. The front yard was freshly mowed, with the flower beds on either side of the porch steps. It was a modest, two-bedroom house, with not a whole lot of backyard space, but it was the most rent she could afford with her previous salary. It didn’t matter though; you could make a house a home no matter how big or small it was. Her job as a teacher wasn’t just rewarding when the kids did well, but it was able to put a roof over her head, and that was all she could ask for.

 

Y/N started with her bags before she opened the large U-Haul trailer attached to her car, and started taking out the boxes. It had been a long journey from Rhinebeck, New York, stopping off overnight in Ohio and then Missouri, but she made it to Lawrence, Kansas that morning, giving her enough time to start unloading her things. Considering it was just her, she knew it was going to take some time, but she was hoping to finish by lunch time so she could explore the town a little.

 

Luckily for her, complicated things to move like a couch and a bed, weren’t things that she had brought with her. Those things were reminders of what she had done on them with her ex-boyfriend and the last thing she needed in her new house were memories of him. He was the reason she had searched for teaching jobs outside of New York, and luckily, she got the furthest one. She missed her family already, but she needed to get as far away from the memories of him as possible.

 

Moving her bags and the boxes from the trailer had been the easiest part. It was moving the furniture – dining table and chairs, armchairs, record player, coffee table and two bookshelves – that was going to be the hard task on her own. She started with what she could do on her own, moving all the dining chairs into the house. When she got back to the trailer, she sighed heavily. There were too many things to move.

 

Y/N stepped into the trailer and started to shift one of the armchairs but growled in frustration as it got stuck on the edge. She couldn’t get the right hold on it to get it off the edge, her legs shaking as she tried to keep it steady.

“Whoa, hey. Let me help you with that” a male voice said behind her. She didn’t turn to see him yet, but watched as he grabbed the other end of the armchair and helped her put it down on the pavement.

“Thanks” she smiled, relieved.

“No problem” he said as he turned to face her.

She almost wished he hadn’t because now her legs were shaking more than they were when she couldn’t hold the damn chair. He was the most beautiful man she had ever seen, handsome but incredibly hot at the same time. The black and white plaid shirt he was wearing was tight across his arms, and she couldn’t help but get lost in his gorgeous green eyes and sinfully pouty lips.

She smiled politely, keeping the thoughts she was having suddenly, at bay. “No, really, thanks so much. I probably would’ve ended up trapped under this chair if you hadn’t stepped in.”

He laughed, laughter lines appearing near his mouth and crinkles around his eyes. “Well, I would’ve hated to see that happen.”

She smiled, not knowing what else to say to him. This was the first time she had ever been this flustered with a man. The sound of his laugh and the way those lines appeared around the creases of his eyes made her heart flutter.

“Can I help you with rest? I mean, I gotta get to work but I can be a little late” he asked, as he looked between the chair and the rest of her stuff.

She looked at the rest of the things and frowned. “You sure? I wouldn’t want to get you in trouble.”

“I’m positive. Helps to be the boss, so…” he smirked, as he shrugged.

She nodded, impressed. “What do you do?”

“I’m a mechanic, I own the auto shop on Main street. Winchester’s. I’m Dean, by the way” he said, as he offered his hand.

She took his hand in hers and tried to ignore the spark she felt radiate through her when their skin touched. “Y/N Y/L/N.”

“Good to meet ya, Y/N” he smiled.

 

When she smiled in return, Dean was completely floored by her. She was beautiful; dressed in loose boyfriend jeans, a white t-shirt, red converse sneakers and a red bandana around her head with her Y/H/C hair in a messy bun. She really had the girl next door vibe going on. That was dangerous with the situation he was in, so he had to tread lightly. When he saw her from across the street, he was reluctant to help because one look at her, even from a distance and he knew he was in trouble. His mother raised him to be a gentleman though, so he couldn’t hesitate to help a person in need.

 

With Dean’s help, moving the furniture she did have into the house only took about 20 minutes. She was incredibly thankful for him helping and hoped that it wouldn’t have been too forward to ask if he wanted to grab dinner with her, that night. She straightened out the medium sized, round dining table and chairs with Dean, and sighed in relief once it was done. Her furniture was now in place in all the appropriate rooms. She had to unpack now, which was almost harder than this, but at least she could take her time with it.

 

Dean looked around her house and nodded, noticing how many boxes had “BOOKS” written on them in black marker. He had only been in this house twice, when the previous owners still lived there before they moved to be closer to their children.

“Big reader?” he gestured towards the boxes.

“Definitely, but I’m a teacher too, so it’s an abundance of books” she laughed, as she looked at them. “It’s a little ridiculous, really.”

Dean laughed quietly to himself, trying to get the teacher fantasies out of his head. She really had to be a teacher.

“Well, I should head out” he said, as he made his way to the door.

She followed behind him and leaned against the doorway. “Thanks for the chivalry.”

“You’re welcome. I guess it’s not dead, after all” he smirked.

She laughed; it felt like the millionth time in the last 20 minutes. He was carefree and had made the tedious process so much easier with his humour.

“I’ll see ya around, Y/N” Dean said, shoving his hands into his pockets as he turned away from her.

“Thanks again” she called out.

 

Dean walked down the porch steps and turned back. He gave her wink before he walked across the street. She sighed to herself as she watched him walk away, his dark blue jeans doing wonders for his behind, though the black and white plaid was hiding his back from the looseness. She thought against asking him for dinner just yet, at least not on her first day in town. She would give it a couple of weeks, enough time for her to settle into her new job and into the town.

 

Y/N closed the door and walked back into the main room. Looking at the boxes, she knew it was better to return the trailer to the Lawrence location and then explore the town a little. Get some lunch, do a little grocery shopping. She picked up her bag and keys, heading out of her new house. She would start on the boxes when she got back.

 

Before she got in the car, she fired off a quick message to her family, telling them she had gotten there safely. It had been text after text and call after call asking if she was okay when she left Rhineback to drive to Lawrence. She reassured her family that all was well, and then drove into town.

 


 

The next day, Y/N was thankful that it was a Saturday. It would give her some more time to set up the house but also start getting ready for the first day of school on Monday. She was nervous about meeting the staff and the students, but she was excited about the new experience. She had walked through town the day before, grabbed the essentials like bedsheets and towels, plus some grocery items for the immediate need. She was already beginning to like Lawrence.

 

The first thing she did was set up the record player her dad had given to her. Once everything was plugged in where it was supposed to be, she put on one of Creedence Clearwater Revival’s records. She bopped her head along to Lookin’ Out My Back Door as she started to unpack the other records, before starting on the other boxes.

 

About 15 minutes later, as I Heard It Through The Grapevine played, she stood on the front porch, watching her furniture delivery unload from the truck. Before she even got to Lawrence, she had bought a new bed frame and mattress, couch, office desk and chair online, and thank goodness the place had Saturday delivery. She had made a makeshift bed out her new sheets and pillows last night, and with the way her back clicked and cracked into place when she woke up that morning, she was incredibly fortunate that her new bed was here.

 

She followed them inside and instructed the delivery guys on where to put the items. As she was helping them, she heard a loud knock on the open door. She turned around and saw a woman, maybe her age or a few years older, standing at the door. Next to her, stood a young boy, probably about 13 years old. Y/N smiled as she walked to the door, seeing a plate of something in the woman’s hands.

“Hi, we saw you moving in and wanted to welcome you. I’m Lisa Braeden, and this is my son, Ben” she introduced themselves, with a bright smile.

Y/N shook her hand and smiled in return. “It’s great to meet you, guys. I’m Y/N Y/L/N.”

“These are for you, I hope you like chocolate chip” Lisa said, handing her the plate of cookies.

“Maybe a little too much” Y/N laughed. “Thanks.”

“Listen, if there’s anything you need, we’re right across the street” Lisa gestured behind her to the house across the street.

Y/N nodded as she looked at the place. It had darker features, but the lawn was equally maintained. “I appreciate that.”

“So, Ben. What grade are you in?” Y/N asked, wanting to engage with Ben a little, who looked quite bored.

“I’m starting 8th on Monday” he mumbled.

Y/N smiled, looking between him and Lisa. “Well, I’m starting work on Monday. Maybe I’ll have you in my English class.”

“Cool.” Ben didn’t seem to care. “Nice choice” he said, gesturing to where the music was coming from before he turned away, walking to the porch stairs and waiting for Lisa.

Lisa looked at him with a “we’ll talk later” look, before she turned to Y/N. “He shouldn’t give you too much trouble, but if he does, you know where I am.”

“I’m sure it’ll be fine” Y/N shook her head.

“Anyway, we should go. Welcome to the neighborhood” Lisa said, smiling again.

“Thanks” Y/N smiled.

 

She watched as Lisa and Ben walked across the street, clearly waiting to be behind closed doors before she talked to him about what just happened. Hopefully she wasn’t too harsh on him; no kid would want to meet their new teacher outside of a school setting. Y/N walked inside the house and saw that the delivery guys were done. She signed off on the delivery and the guys left. She picked up one of the boxes still in her living room and walked to the second bedroom she was using as an office. She was excited to set it up and get started on some work for Monday.

 


 

Y/N sat in her car in the parking lot of the school. She had gotten there a little early, just trying to calm herself down before going in to meet the principal. She had spoken to him for her phone interview and again when she got the job, so she was familiar with him. He seemed like a nice man and she just hoped that the rest of the staff were the same way. She was more nervous about the students. Moving schools wasn’t just hard as a kid.

 

She checked her make-up in the mirror and then got out of the car, walking towards the entrance. She fixed her white top and smoothed down her brown skirt, thankful that she had chosen brown sandals with a small heel instead of something higher. She didn’t need anything to go wrong today. Once inside, she walked over to the administration office, as guided by the signs. At the very first desk, sat a red-headed woman, the name plate on her desk reading: Anna Milton – Receptionist.

 

When Y/N approached her desk, she looked up from her computer and smiled.

“Hello, how can I help you?” she asked.

“Uh, hi, I’m Y/N Y/L/N. I’m starting here today and need to meet Mr. Shurley first” Y/N replied, trying her best to keep her nerves at bay.

“Oh of course” she picked up the phone and pressed a number.

 

Y/N waited a minute or so before a short man with greying hair and a beard, walked out of an office at the back of the room. He saw her and smiled, extending his hand as he approached her.

“Miss Y/L/N, wonderful to meet you” he said, shaking her hand.

“You too, Mr. Shurley” she smiled, as confidently as she could.

“Alright, let me show you around before your first class” he walked ahead of her, not leaving her too far behind.

 

It took Chuck, as he insisted on being called by his first name when it was a one-on-one basis, a few minutes to show her around the main parts of the school; the staff room, the library, the gym and the cafeteria. After that, he took her to the classroom she’d be using, just before the students came in. They watched as they came in, sitting down at their desks. Ben walked in and she smiled at him, but just received a little twitch of his face back. They all looked scared to see the principal in the room.

“Class, I’d like you meet Miss Y/L/N. Your new English teacher. So, make her feel welcome” he said to them in a commanding voice, before he turned to her. “If any of them give you any trouble, just send them down to my office.”

“I’m sure I won’t need to” Y/N looked between him and the students.

“Alright, take it away” he smiled before he left the room.

 

As soon as he was gone, the class erupted into loud voices as they began chatting away. Y/N sat on the edge of her desk, her legs and arms crossed as she waited, patiently. She would give them a few seconds before she got their attention. Before she could do that however, Ben looked at her and then at the rest of his classmates.

“Guys” he called out. The noise level didn’t go down.

“Last one to be quiet has to tell their next teacher why they were late” she called out.

The noise level dropped instantly.

Y/N smiled, happy that worked. “Alright. As Mr. Shurley said, I’m Miss Y/L/N. We’re going to start off with the role. As I call out your names, you’re going to tell me what you read over the summer and a short answer about what you liked or didn’t like about it.”

 

For majority of the class, things went well. Most of the students were well behaved except for one group of three boys who kept talking and disrupting the others around them. They were rude and weren’t listening to her when she asked them to stop several times. She would have to keep an eye on them. To say that her first lesson had been difficult would be an understatement, but she got through it. That’s what mattered.

 

Y/N had a break in which prepared for her class with the 7th graders. They were a breath of fresh air and exactly what she needed after the previous class. They were much more engaged and a lot softer spoken, so while she would have to get them out of their shells a little bit, they were pretty well behaved.

 

At lunch, Chuck introduced her to a few more of the teachers. She shook hands with everyone and engaged in conversation. The usual chatter about where she was from and how she got into teaching. As she sat down to eat, she looked over some of her messages. She smiled as she saw one from her sister, sending off a quick reply to tell her she was doing okay.

“Mind if I join you?” a voice asked.

She looked up to see a man with brown short hair and blue eyes smiling at her. He was adorable, looking cute in his white shirt with rolled sleeves, black pants and blue tie to match his eyes.

She smiled in return and nodded. “Sure, of course.”

He sat down across from her with his lunch. “I’m Castiel Novak, history teacher. Everyone calls me Cas, though.”

He offered up his hand and she shook it. “It’s great to meet you.”

Just as he was about to say something, a red-headed woman, not Anna, walked over. “Hey, you must be the new English teacher, I’m Charlie.”

“I’m Y/N” she said, shaking her hand.

“Charlie teaches Math but she’s a computer whiz too. Helps out the I.T. guys every now and then” Cas told her as Charlie settled into the seat next to him.

Y/N smiled approvingly. “Wow, that’s amazing.”

“Thanks. They ask me because I think they secretly know I’m better at it than them. I was in the corporate line for a while, but then I moved back home to help my mom” Charlie explained, between bites of her salad.

Y/N liked her already, her nerdy vibe with colourful plaid shirt and band t-shirt suiting her chirpy personality. Cas was a little quiet, but there was a calm presence to him. Though she had no doubt he had the ability to get kids to listen to him straight away.

“Yeah, we’re all glad she came back and stuck around” Cas smiled at her.

When she smiled in return, Y/N had to ask. “So, you two…?”

They both laughed as they looked at each other and then back at Y/N.

“No, we’ve just been friends for a really long time. I have a girlfriend, Meg. She’s a nurse at Lawrence General. She’s tougher than nails and I don’t know how I got her” Cas replied, laughing slightly.

“Yeah, and I’ve just started dating a few weeks ago. Her name’s Dorothy and she’s a writer for the Kansas City Times. She’s really cool” Charlie smiled softly.

Y/N nodded, understanding. “They both sound amazing. I can’t wait to meet them some time.”

 

They continued talking over lunch and Y/N couldn’t have been happier to have met them. They were both incredibly kind and lovely people, and she was really starting to get along with them.

 

As lunch finished and they went their separate ways, Y/N smiled as she walked to her next class.

 

Hopefully moving to Lawrence, Kansas was going to be the best decision she’d ever made.