Turns out that the School had the day all planned out the buddies would meet after Homeroom where they had to play nice with the parents and meet the kids in the main foyer, before heading off to the gymnasium for the day. That is except Dean, apparently his little buddy is going to be meeting him in homeroom.

"Hey, Mr. Drew I came early, I was wondering about my little buddy?"

Before Mr. Drew could answer a voice came from the back of the room "…but uncle Peter what if Dean hates me?" making Dean turn to stare at Peter Hale the kid who seems to hate him and Sam on sight, holding onto a little five year old with black hair that seems to defy gravity, and green eyes staring intently at the Sophomore waiting for an answer.

"I am sure Dean won't hate you." Peter Smiles at the little boy, before sending a slight glare at Dean. "Or Hurt you" Peter winks at the boy before giving a smile to their teacher.

"Peter, I hope Talia is well." Mr. Drew askes making small talk with Peter while the Kid sneaks peeks at Dean from where he hid his face into his uncles neck.

"Yes, of course Mr. Drew. Just she is on bed rest seems little Cora is wanting to be born early, and Erik just drops us all off at school then goes home just in case."

"Ahh yes this will be Talia's third child right" the conversation continues as Peter absently places the kid onto a chair beside him, the Kid is still staring at Dean with wide eyes but he won't let go of his uncle. Dean waves at him making him burrow a bit into Peters side.

"That is correct, Laura is already in the 3rd grade, and Derek here has a head start on 1st grade material." Peter states proudly. That's when the rest of the Homeroom comes in ready for attendance and announcements. The girls all coo at the little boy sitting beside Peter, even with Peter having the aura of "fuck off", and the kid deals with all the attention by scrunching up even closer to Peter practically in his lap.

"So that's your buddy?" Sam looks between his brother and the child trying to melt into Peter's side as more and more people come in.

"Yeah, he's Hale's nephew apparently." Dean replies.

Homeroom continues on as usual only interrupted by Peter assuring Derek that everything will go okay today, and that it will be fun. With the announcements ending, everyone files out, Sam being one of the last people out wishes Dean luck, and when it was just the three of them Peter addresses Dean.

"Winchester, you better not even look at my nephew the wrong way or I will end you as slowly and as painfully as I can." Peter threatens glaring up at Dean.

Swallowing Dean nods "I get it man, just I won't hurt him I promise." Dean backs away from those intense blue eyes staring at him, while the kid has somehow found his chest the most interesting thing in the room.

"Good," Peter sounded satisfied and breaks eye contact before kneeling down in front of his nephew who looks less scared then before his uncle's threat. "Derek, be good for Dean and the teacher alright" the kid nods "do you remember the rules." Dean frowned a bit at that as the kid nods again "good boy, now Dean is going to take you to the Gym where you will be with your teacher and classmates okay, now be the little gentleman I know you are and say hi to Dean"

"Okay Uncle Peter." Derek nods once more before hopping off the chair and holding out his hand to dean, "Nice to meet you mister."

Dean looks towards Peter for guidance, getting a nod of approval he bends down and takes the kids hand "nice to meet you too, Derek, you can call me Dean." Dean puts on his most charming smile before straightening up, and letting the child keep hold of his hand. Peter watches the interaction like a hawk, seemingly satisfied with the result he reminds Derek to hold Deans hand whenever they walk through the halls before leaving the two behind.

"Alright, Derek are you ready to go meet up with the others?"

"Yes, Dean" Derek answers obediently and leads them towards the door before allowing Dean to guide him.

The walk to the Gym was slower than usual for obvious reasons, but Derek filled the time talking about his little friends, and about the teachers he has, and how he was special because he knew joined up writing already, and maths. Dean nodded along and answered when necessary, actually paying attention to the babble, because he was going to be spending one day a week with the kid for the next three months. Upon entering the gym, it was like walking into chaos incarnate children's screams and cries were echoing off the walls and the senior Buddies were looking confused and distraught chasing after their charges, while the teachers seemed more concerned with their camera having film, and were quite content allowing the children to burn off energy before the day's activities began. Dean led Derek towards the tables that were put out for the group and thanked everything he knew existed that the child he was paired with was calm and well behaved kid, earning glares from his classmates, trying to catch, or at the very least make sure the children didn't run head first into anything.

"Don't you want to play with your Friend Tommy was it?" dean asked after a few minutes of him twiddling his thumbs and Derek swinging his legs watching the others play tag.

Derek absolutely beamed at Dean because he remembered his best friends name "Tommy is mad at me because I won the sports day relay and he says he's the best runner ever but " Derek looks around before stage whispering "but I am faster than him I just let him win most of the time because it's nice " Dean grins and tells the kid it makes Derek really nice, wondering if that is one of the mystery rules Derek has to follow ", so I try not to run to much with him, because I like tommy, and because I am taking big kid classes we can't play as much as before." Derek's voice steadily rises to normal volume.

Not soon enough for the other seniors the Kindergarten teacher corals the little ones to the tables where Dean and Derek are already sitting and instruct them to match up with their buddies. The first order of business is to create name tags, so Dean takes off his Leather jacket before rolling up Derek's sleeves so they won't get too gluey. At the end of the assignment some of the other seniors look ready to cry, while dean himself is covered in gold sparkles and Derek has red and black marker on his hands. It's not nearly as bad as the stuck up boy Curtis who somehow got glue and pink glitter in his hair, and the holier than thou girl named Ariel who let her little buddy near the scissors and now has a few scratches on her arm as well as a couple of holes in her shirt. Not for the first time Dean thought it was a bad idea to allow stressed out teens to be even slightly in charge of kids just above toddlers.

Once people were clean and in some cases bandaged up. The teacher suggested a game of Go,Go, Stop! This caused a cheer from the kindergarteners, and one Senior named Derek Matthews, who all boasted about being the greatest at the game, the first round was a practice one, thankfully, for the out of depth seniors who looked rather wide eyed when the teacher put on music causing the kids to start dancing and wiggling about in the most ridiculous manner while forcing the teens to dance with them, when the music suddenly ended causing the children that were jumping to thump to the ground absolutely statue like, in turn making the unprepared teens to stumble while their hands were in the vice like grip only children seemed to have. The teens quickly got the idea, if only because a 5 year old glaring at you to not mess up was absolutely terrifying especially after the promise of a prize for the last one standing. Once again Derek proved to be somewhat more subdued than other kids when all he did for dancing was a few simple ballroom steps Dean himself remembered his mom doing with him while the other children either were just hopping, twirling, or trying to break dance in the Matthew's brother's case, who were unsurprisingly the first group out but continued dancing anyway. Derek again shows either his way to niceness or it was the odd set of rules he needed to follow, when it was just Dean and Derek, and Curtis and his Little Buddy named Emma left, Derek did a daring spin at the end of the song causing him to stumble and lose the game. Dean didn't mention it as he himself have been told not to stand out too much when younger, not like he ever had time to anyway.

"Tough luck that Winchester, I know how you like winning." Curtis told him with a matter of fact tone while being given a fun sized candy by the teacher. The Statement made Derek look a bit concerned at his purposeful loss.

"Wilcox, you don't know anything about me, I don't have to win, and just because I do beat you most of the time in class doesn't mean I like winning." Dean smirked "It's not like I even try"

Derek stared wide eyed at Dean's chest again "you're really smart like me, and Uncle Peter"

Dean blushes and rubs his shirt, before the Teacher gets their attention again and has a lunch laid out evenly on the tables "come on lets go eat with your friend, Derek."

"Okay" Derek drags him towards two kids animatedly talking to each other "Dean this is Tommy," Derek points to a little wisp of a kid who was all eyes it seems. "And that's Kyle." Derek pulls Dean down so he can 'whisper', "Kyle isn't really my friend though, but we are nice to each other, he's really shy" Dean admits he was rather surprised at that considering the kids older brother doesn't have a meek bone in his body.

"Hello," Dean Smiles at the kid, "Derek has told me about you, it's nice to meet you." the boy acts a little shy only waving at him instead of a vocal greeting. Dean just smiles and grabs a few wet wipes that are spread around the tables and proceeds to wipe Derek's hands and his own before suggesting the other boy should wipe his hands as well. Dean Plates a bit of everything on Derek's plate before doing the same for himself. "Derek you, don't have to eat anything you don't like, but I would like to see at least one veggie and one fruit missing off your plate is that fair?" Dean asks the kid staring horrified at the two bits of raw broccoli on his plate. Cataloging the other food items on his plate Derek nods in agreement.

"You're really good with kids" says the kindergarten teacher.

"Thank-you ms…" Dean Blushes before Derek pulls Deans head down to stage whispers his teachers name "... Wagstaff" Dean winks at Derek in thanks before he continues talking to the teacher "I helped a lot with my brother, especially after my mother died "Dean let his smile dim a bit, this statement usually got him out of trouble, or extra food, but today all it caused was gasps from the little kids around him, and a sympathetic look from the older Matthews.

"Your mommy is in heaven?" tears were almost coming out of Derek's eyes

"Yeah she is." Dean said softly.

"Who looks after you?" asked Tommy

"My dad, and we have Bobby, he's like an uncle to us" Dean answers watching as the kids absently nibble on their carrot sticks.

"Who scares away Monsters?" Tommy asked looking behind him as if monsters would be there.

Dean tenses at the question, but before he even tries to answer the teacher gives Dean her condolences.

"Oh I am so sorry to hear that Dean" the teacher pats his shoulder.

Before moving over to a different table.

Dean clears his throat. "Great Job Derek, you ate two types of veggies, I think you deserve a treat" Dean Looks at the rest surprisingly it was actually the meat that Derek didn't touch, making sure the teacher wasn't around dean quickly pulled out a chocolate bar he hid in his jacket, and gave the kid half of his Twix causing his buddy Derek to smile and lose the sad eyes. And causing the older Derek to laugh, considering the Teacher was giving out candy the whole day. Dean just shrugged in response it made the chocolate taste better if thought to be sneaked.

The rest of the day went by like the first half with Derek always being second best unless it came to intelligence or arts and crafts, pretty much confirming that those are at least part of the strange rules that Derek needs to follow and remember. Dean walked out of the gymnasium with Derek attached to his arm and headed to the main foyer where the parents were supposed to meet their children.

Derek started pulling Dean towards a man and a girl who was fighting …With Peter who just held her at arm's length away while he played with his weird phone one handed.

"Daddy!" Derek said in lieu of greeting still dragging Dean behind him, this got everyone's attention.

"Hey Der-bear who is this?" the man answered. While the girl hid slightly behind her father.

"This is my Buddy Dean, he's smart like me and Peter, and he's really good at dancing, and his mommy is in heaven," Derek looked sad again "but he gave me chocolate because I ate my carrots and celery at lunch, and he's really nice because he didn't make me eat broccoli, and he's good at basketball, but not as good as you uncle Peter, because Peter is the bestest, and he's a good drawer like me too."

"Hey kiddo breathe, I am glad you had fun today." The man looked apologetic at Dean "nice to meet you, I'm Derek's dad Erik." He held out his hand for Dean.

"Nice to meet you Erik, I'm Dean…obviously." Dean blushed a bit as he returned the hand shake, never being all that good with adults.

"Oh god Derek didn't bite you did he?" Erik said looking at Deans bandaged hand that he still held in his own.

"What?" Dean pulled his hand away before explaining the bandage "oh no, uhh a girl was arguing with her little Buddy about using scissors again, and they ended up being thrown in Derek's direction I just happened to block the blades with my hand instead of them stopping in poor Derek's face."

"That's good, Laura bit her Buddy just had to make sure." Causing the girl to squeak and huff in anger, before blushing at Dean when she noticed him looking at her.

"See my picture daddy, Dean said I should make another one but I don't mind his blood being on it." Derek showed them his picture that he pulled out from under his shirt of stick figure representation of himself and Dean dancing where he artistically made the blood splatter into music notes, there were only three drops and Dean tried his best to wipe them off. "See the blood daddy, another person named Derek helped me finish it, isn't that cool someone else is named like me."

"That is very cool that you met someone with your name, and the picture is … umm lovely "Erik's smile seems a little more fixed towards the end of the statement.

"You finished it, I thought the teacher threw it out?" Dean asked perplexed he swore the teacher picked it up and placed it by the bin.

"Nope, big Derek got it for me and I fixed it and hid it in my shirt when Mrs. Wagstaff went and fixed your owwie" Derek said proudly. Getting even more laughter from Peter. "Can I hang my picture up in my room when we get home daddy?" Dean is surprised peter isn't on the floor at this point, but knows for a fact that there is a picture on his really weird phone, who needs a camera on their phone anyway.

"We will ask mommy first, okay kid" Erik patted his kid on the head "speaking of mommy it's time to go home and see her, say good bye to Dean. Oh and Dean thanks for taking care of Derek all day"

"Not a problem" dean said with a smile, before getting hugged around the middle by Derek

"Bye Dean, sorry you got an owwie today."

"Don't worry about it, it only stings a little bit now, and I will see you next week okay." Dean barely touched the kids shoulder before he darted away with his family.

Dean walked out into the parking lot towards the impala Sammy was leaning against. He started his car and gave a small wave to Derek who was being strapped into a booster seat in the back of an SUV. Derek returned the wave wide eyed and awed at the Black car rumbling by.