Hello and thank you for stopping by to check out our story! This story was co-created/co-written with the fabulous Nevertoomany. Be sure to check out her sisfic as well! She's a talented writer :)

We hope this story will become a series of one shots with our character Maddie at different stages in her life. If you're curious about anything, don't be shy and let us know! We'd love to hear ideas of what you'd like to see/find out in future chapters.

This was a lot of fun to write, so we really hope you enjoy it as much as we did. Leave us a review and let us know your thoughts!

Happy Thanksgiving!

This takes place during season 9.


Dean: 34

Sam: 30

Maddie: 5

Two years with a little girl teaches you a lot about life. For example, Dean learned that cereal tastes as good on a table as it does in a bowl. And sometimes the dark can have good monsters, not just bad ones. Life with a little girl was not always easy, but it definitely had its benefits. She was a great source of laughter and comfort after he'd come back from working a hard case. Her innocent smile was enough to wash Dean's lingering pain away, even if it was only momentarily.

There was never a dull moment around the bunker anymore with a rambunctious five year old on the loose. For Sam and Dean, growing up in motel rooms meant child-proofing things was irrelevant. There was never much of anything the boys could get into, but now with a batcave that had countless rooms, it was merely impossible to keep her out of everything. There was a hidden adventure waiting for little Maddie around every corner, always keeping her dad and uncle on their toes. She was always active, so more than thirty seconds of silence meant trouble.

But today was different. Her latest adventure awaited outside those concrete walls, in a place where she'd start her thirteen year journey, a place Dean had often referred to as hell, but to the normal person, or Sam for that matter, it was simply called school. And today she was finally going to start Kindergarten.

Dean treaded carefully as he walked to his little girl's bedroom. He twisted the knob and walked into the darkened room. Little snores emitted from Maddie as Dean walked towards her. Keeping the light off, he laid his hand on her back and stirred her awake.

"Maddie, wake up, kiddo. Time for school," he whispered. The little girl stirred and rubbed her eyes before burying her head back into the pillow.

"No," she moaned. "I don't wanna go!"

Dean closed his eyes and took a deep breath, readying himself for what was sure to be a tiring battle this morning. "You have to go," he replied matter-of-factly. But logic never appealed to a five year old.

Maddie sat up in bed, her wavy brown hair sticking out in all directions. Crossing her arms over her chest, she pouted, "But I don't wanna, Daddy!"

Seeing that she was now awake, Dean walked back over and turned on the light. "We talked about this last night, remember?"


"Maddie," he warned.

Every bone in her small frame wanted to continue arguing with her father, but when she finally caught a glimpse of his stern face, she decided to back down for now and just stare at him, not willing to move just yet.

"Why don't you get your clothes on," he said motioned to the outfit he'd laid out the night before, "and come downstairs. Uncle Sam made pancakes."

Her crystal blue eyes lit up at the mention of her favorite breakfast food. Just like Dean, the girl could easily be persuaded with food. "Chocolate chip?" she asked, excitement in her voice.

"You'll have to hurry up to find out," Dean replied, smiling as she bounced out of bed and over to her clothes. He walked out of her room and down to the kitchen chuckling. Maybe this morning wouldn't be so bad after all.

Five minutes later, Maddie bounded into the kitchen with a smile plastered on her face. Sam sat at the table with a coffee cup in his hand and a laptop in front of his face. Dean sat in the chair next to him, cutting up his pancake and shoving it in his mouth. Maddie sat down in the chair across from her father and pulled her plate close to her.

"Hey, good morning," Sam announced as he looked over at his niece. She would've answered, but her mouth was already full of pancakes. Chocolate chip, as promised. "You excited for your first day of school?"

Maddie stopped shoving pancake in her mouth and looked down, swallowing. "I don't wanna go," she mumbled.

Dean just looked at Sam, giving him an annoyed glare. Of course he had to ask that question! He had convinced her to come downstairs in peace, but not even five minutes later and Sam had to start up the morning drama again. "Maddie, come on. We're not arguing about it today."

"I wanna stay with you!" she said, her eyes filled with sadness at the mere thought of being separated from the only parent she really had any memory of.

Sam instantly picked up on the impending argument and jumped in to help. "School is fun! You'll get to play with kids your own age and even learn to read!"

Maddie stared at him, luling over his words before asking, "Will I be able to read big person books like you?" She motioned toward the bookshelves and stacks of lore books on the table in the study.

"Yes, some day you'll be an even better reader than your dad." Sam smirked, but was met with a playful shove from his brother.

Maddie giggled, seeing the interaction between the two. Being better than her father at something sounding so appealing, like a shiny object she just wanted to have. "'Kay. I think I better read Curious George first. His books have cool pictures, not yours."

"Can't argue with you there," Dean admitted and finished up his pancake. Maddie finished her pancake, too, and Dean pushed her off to go finish getting ready. As she bounded out of the room, Dean turned to Sam as he picked up his daughter's plate. "Sam, mark my words, she will never read a lore book ever. You got me?" He placed her plate along with his in the sink and glanced towards his brother.

"Hey, I'm right with you there, man," Sam agreed and took a sip of his coffee. "She needs to be kept away from the life for as long as she can."

"She'll never see any part of it if I have any say in it," Dean muttered and walked out of the room. He wandered slowly down the hall towards his daughter's bathroom and knocked on the door. "You almost ready, kiddo?" The door swung open and Maddie stood there with a brush in her hand and a clump of knotted hair in her other.

"We have a problem," she admitted and tried running the brush through the knot but only got it stuck again. She sighed and looked up at her dad. A smile cracked his lips and a chuckled escaped him.

"I'd say we do," Dean chuckled again and open the door more. "Let's see if we can conquer this beast, huh?" Dean asked as he picked up the little girl and placed her on the counter.

Dean had finally managed to untangle her ratty hair and get her out into the Impala and on their way to school. Sam had been forced to stay behind because Dean said he'd only make things more difficult for Maddie with all his high praises of school and learning.

As they were cruising down the road, Dean glanced in the rearview mirror at his daughter. She sat in her booster seat with her Batman backpack clutched tightly to her chest as she stared out the window, biting her bottom lip. Dean had always been very observant of everything that had to do with Maddie and he knew that sign. When she bit her lip, it was because she was nervous.

He sighed, turning up the music a little louder to drown out his thoughts about what was to come. His plan had been to quickly go and drop her off at the classroom and then get out of there like a bat out of hell. Like ripping a band-aid off, the faster the better. But the look on Maddie's face told him things may not go down quite that easily.

As Dean pulled into the school parking lot, he gazed at all the kids streaming about. Kids Maddie's age clutched his or her parent's hand and walked into a different doorway than the older kids; the rest of the kids glided happily through the main door. Some infants and toddlers were gripped in arms and a few were screaming their heads off. Buses and cars and various people were everywhere, threatening to give Dean a headache.

Dean parked the Impala and climbed out, immediately immersed in the chaos of first days. Oh, how he had come to loathe those days (which seemed to be more abundant in his childhood). The uncertainty, the confusion, the worries; it was all so much for such a little task. And here he was again, putting another little kid through the mess that was first days. If homeschooling was an option for them, public school would've never even been considered.

As Maddie climbed out after him, she pulled on her backpack and gripped her father's hand tightly. He held back and took a deep breath, preparing himself for a quick child stash-and-run. Finally, he crossed the parking lot and led her towards the school building. As they walked, he peeked down at his daughter and noticed her glancing around at all the children. Her eyes showed slight fear as she gripped his hand tighter.

The two slowly made their way down the hall. Neither spoke as they took in everything around them, all the squealing of excited kids when they stepped inside the room, the excited laughter, overeager teachers, and the occasional tears from both children and parents (causing an eye roll from Dean at such theatrics). There were three kindergarten rooms at the end of the long hall, decorated with distinct paper flowers on the bulletin board outside that listed the students assigned to each room.

His eyes rapidly scanned each wall until they finally spotted "Madeline Winchester."

"Daddy, look my name!" Maddie exclaimed, jumping up to point to the flower.

Dean smiled to himself. "Yeah it is," he confirmed, even though she didn't need it. He glanced around and noticed that only parents were looking for their child's name. He instantly filled with pride that his girl was already more advanced than these other snot nosed brats. Although much of the credit went to Sam's constant insisting that she start learning from an early age, he knew it had more to do with his genes. Yeah, she was destined to be intelligent because of him. It was in her blood.

"Let's go inside and meet your teacher," Dean said as he started for the door.

"Wait!" Maddie shouted, panic clear in her voice. She quickly hurried over to him and clutched his hand tightly again before they stepped inside of the noisy, busy classroom. There were so many kids running around playing with all kinds of toys that Dean could already feel a headache coming on.

Just then a younger, blonde haired woman dressed in a long, beige skirt and black sweater came approached them. She kneeled down to the little girl. "Hi, sweetie! My name is Miss Clark. What's yours?"

Maddie didn't respond, but instead only pulled herself in closer to her father, reaching out with her other hand and clasping onto his jeans in fear.

Dean looked down when he noticed his little girl hadn't answered a simple question. "Go on, tell her your name," he encouraged a little forcefully. Maddie let go of Dean's hand and wrapped her other arm around Dean's leg. She burrowed her face in his pants, trying to block out all the noises and people. Dean looked over at Miss Clark as she stood up. "I'm sorry, she's never this shy," Dean explained with a smile, as his small apologies were always laced with a smile. "Usually, she's bouncing off the walls at home."

Miss Clark smiled back. "It's fine, I understand. I've had plenty kids that were shy on the first day. It's just something we'll have to overcome." Both adults looked down at Maddie, but she still clung to Dean's leg.

"I'm Dean, by the way." Giving up on Maddie a few seconds later, Dean changed the topic. There was a hot, young woman standing in front of him, after all. He wasn't going to let his shy daughter get in the way of this opportunity. His emerald green eyes locked with the teacher's piercing blue ones. And then the classic grin came to follow.

Miss Clark smiled softly, momentarily caught up in his gaze. "Kayla."

Just then a little blonde haired girl skipped her way over to Maddie, on the prowl for a new friend since her parents had already left her behind. "Hey, wanna play?" she asked, not even picking up on the adults around her or the fact that Maddie was clinging desperately to Dean's leg still.

Dean saw this as his window of opportunity. He knelt down and pried her small hands off of him. "Look, Maddie, a new friend!" he said with fake enthusiasm, hoping she'd buy into it.

"But I wanna play with you, Daddy." Her bottom lip stuck out in a quivering pout, but he refused to let it affect him this time.

"We can play Barbie dolls!" the little Kindergartener exclaimed with joy.

Maddie looked between her friend and the two adults, seeking some kind of clarification. "What's that?" she asked innocently.

Dean could feel Kayla's confused gaze boring into him, but he chose not to look up and just shrugged. What did she expect? There was no way in hell Dean had ever taken her down the little girl aisle at the store, much less actually purchased a Barbie doll for her. Hell no. She had army men, toy cars, and lots of coloring books. That was good enough but now he was hit with the sudden realization that she was going to be introduced to all the crap he'd tried to shield her from, or rather him from.

But he'd deal with that later. Right now, he just wanted to leave his kid in this classroom without any waterworks and make it back to the bunker in one piece. And, he'd be damned, but this was his way out.

"They are pretty cool toys," he cringed as he forced the words to leave his mouth. "Why won't you go see what they are with your new friend?"

Maddie stared at him for a moment, contemplating if what he was saying was real or not. The little girl reached out and grabbed Maddie's hand, ready to take her back to the opposite corner of the room where all the dolls were. Looking quickly between the girl and her father, Maddie relented. She gave her dad a quick hug and goodbye and gripped the little girl's hand again. With one last glance at Dean, Maddie allowed the little girl to lead her away. The girl skipped over to the corner and immediately pulled out a doll she coined as her favorite minutes ago.

"This is Barbie," the girl, named Clara, said as she turned around with the doll in her hand. "Who're you being?"

Maddie looked innocently at her. Clara sighed after realizing she wasn't making a move towards any dolls. She turned back around and picked out the next best doll; she had a big, princess-like dress on and long, brown hair. The hair had about a million knots in it, but other than that the doll was in good shape. Clara handed the doll over to Maddie and announced her doll's name was Stacy.

"Hey, Stacy," Clara talked to her doll in a high pitched voice, "wanna go shopping?" The girls began to play, acting out whatever scenes they could think of and putting their dolls through many different problems. Maddie eventually blended right into the other children. The fact that she hadn't had much time with kids her age didn't seem a problem and affected her in no ways (besides the fact that she didn't know many of the girls' toys, that is).

Meanwhile, Dean stood up and readied himself to face his daughter's teacher. "So school's out at 2:30, right?" he asked, making small talk.

"That's right. Will you be picking Maddie up...or will her…," she trailed off, trying to get information out of him.

Dean smiles wide at the open opportunity to let her know he was single and more than ready to mingle. "I will. It's just me and Maddie." He couldn't help but see the way she bit her bottom lip, trying to hide her eager smile. Oh this one was already in the bag and Dean would have flirted even more, but he caught a glimpse of his daughter playing with her new friend and he knew that if he didn't escape soon, she was bound to turn around and run back over to him and this process would have to start from scratch again.

He flashed Kayla another infamous grin. "So I guess I'll be seeing you a lot this year." And with that, he turned on his heel and slipped out of the door as quickly and quietly as he'd come in. As he walked down the hall, zig zagging right and left to avoid running into all the families blocking his path, he felt a sudden pang in the pit of his stomach, something he hadn't expected in the slightest. His pace slowed as his mind drifted back to his daughter that he'd left behind in that classroom.

Thoughts of whether or not she would be safe and if public school was the best idea for her ran through his brain. He knew what public school was like, and quite frankly, he hated it. Was he really putting his daughter through the same mess he was put through? Granted, they wouldn't be moving around as much as he had, but school could still be hard on a child. The bullying, the stress, the friend troubles, all of it. And the fact that she was a girl going through all that crap, well that was unchartered waters for him.

Slowly, Dean exited the building. Once outside, he glanced back towards the school and saw other parents walking out, some with younger children, some with significant others, and some alone. Most all of them didn't spare another glance towards their children, some walking away looking relieved even. She'll be fine. It's just a couple hours, right? He was Dean freaking Winchester. He could handle this. And if anything ever did go wrong, well, the batcave was only minutes away.

He'd tried to focus his thoughts on guns, monsters, and lore for the entire morning but he just kept reading the same paragraphs over and over. His mind was elsewhere-thinking if Maddie had finally settled in or if she was upset when she realized he wasn't there any more. He'd rarely been away from her over the past few years and even then, she'd been left in the care of someone he knew, not a mystery, albeit hot, teacher.

After a wasted morning, he knew what he had to do. He grabbed his coat and car keys off the table, but ran into Sam on his way to the garage.

"Where are you going?" he asked, checking his watch to see if it was already time to pick up his niece.

"Gonna grab us some lunch," Dean replied with ease, although it wasn't a lie. He'd get lunch, but he'd make a pit stop as well.

Sam just nodded and continued on his way to the den as Dean disappeared out the door.

It only took a few minutes and he was driving by the familiar building from the morning. He just wanted to make sure she was okay. He was acting like a parent, right? Yeah, this wasn't him being overprotective or having any doubts. Psh, that was for lame ass parents. Not him, the cool dad.

He drove slowly along the curb as he scanned the playground. It didn't take him long to see Maddie in her purple shirt and jean shorts. She was running around like crazy, climbing up the playground with a few other kids. He could see her smile and that was all he needed. His kid was happy, she was okay. It eased the pang of worry in his stomach and he even found himself smiling as he drove away. He had had a tiny moment of panic, one that he'd never admit to his brother because he'd only mock him. But Dean Winchester could do this. He could let go and let Maddie live a happy life at school, but man was it hard. However, he knew this would only get easier for the both of them with time.