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It was Dean Winchester’s second year of teaching Kindergarten and Castiel Novak’s first year as a PTO participant. Castiel was sort of late signing up for PTO opportunities, so the only one left was the recess supervisor. Castiel didn’t mind his being the recess supervisor especially since the very hot Kindergarten teacher brought him coffee and cookies everyday. How Mr. Winchester found out his favourite cookie and how he likes his coffee slipped his mind, but Dean remembers it very clearly.
~~~August 5th~~~
Castiel is walking around the school trying to find the teacher in charge of the recess supervisors, when he finds Mr. Winchester dancing in his chair playing on Cool Math, Castiel can’t help but laugh.
In a moment of fear Mr. Winchester slams his laptop shut and spins around in his chair.
“Oh… uh… sorry about that, I was uh….” Dean stammers.
“Haha, no don’t apologize. I loved cool math as a kid, and your dancing wasn’t half bad” Castiel says as he notices Mr. Winchester blushing.
Dean clears his throat and motions for Castiel to sit down “Is there something I can help you with….. I’m sorry I don’t think I know your name”
“Castiel, Castiel Novak” Castiel says as he holds out his hand “I’m the new recess supervisor”
“Oh! That’s right I remember seeing your name on the list. Novak, I like it” Dean says as he shakes Castiel’s hand.
Castiel chuckles. “Well,” Castiel looks at the board behind Dean “Mr. Winchester-”
“D-Dean, You can call me Dean” Dean didn’t understand why he was blubbering like an idiot, it was just a parent volunteer. A very hot volunteer, with a sexy bed head and-- oh those eyes, he couldn’t stop staring at those eyes. Dammit Dean! Get a hold of yourself, he probably doesn’t swing your way. Don’t get your hopes up.
“Okay, Dean.” Castiel paused, “you can call me Castiel”
Castiel smiled a little bit when he saw Dean grin from ear to ear. “Castiel” Dean murmured, still smiling. “Anything I can help you with?”
“Do you have kids?” Castiel said very quickly. “Sorry, didn’t mean to throw that at you, but d-do you?” Castiel asked nervously.
Dean chuckled “No I don’t actually. Uh... Do you?”
Castiel just smiled at him and slightly tilted his head.
Dean buried his face in his hands then looked up, “Yep, realized as soon as I had said it.”
Castiel just kept smiling, “Yeah, her name is Sam”
Dean smiled a little bit at the name of Castiel’s child. Thinking of his brother.
“She is adorable, this morning she tried to make my coffee. She would have gotten it right if she had put something else in it. I woke up to the smell of pure coffee. Black coffee, with nothing in it. I mean I still drank it, but I would have prefered my usual. An espresso with my half & half creamer topped with whipped cream. I love whip cream, always will. After that she wanted to make cookies, she said she wanted to make her favourites and mine. So we made three oatmeal raisin and three gingerbread snaps. I still have some, i-if you want one?” Castiel pulled a small bag with two oatmeal raisin cookies out of his bag and offered Dean one.
Dean took one and laughed. Castiel gave him a look of puzzlement. “Oh sorry, I just haven’t had cookies in a while. I made them for my brother when he was sick, my dad wasn’t around very much, so it’s just funny to be holding a cookie again.”
Castiel just smiled and tilted his head. They talked for what seemed like hours before Castiel had to go. They promised to see each other every time they could-- before school, after and every time in between.
~~~The rest of the school year~~~
Dean and Cas would sneak glances at each other when they thought no one was looking, but of course the kids caught on and would watch it when it happened. After the school day, Cas would usually bring coffee and food to Dean’s house and they would talk for hours. Some days Dean was grading the kids’ work, so Cas would just sit next to him and keep him company.
Dean’s little crush had blown up since that day in August. The kids never stopped asking why they looked at each other like that. Dean would always repeat the same thing.
“We… uh… We’re just really good friends.”
The kids never believed it, but Dean wouldn’t try to explain it any further. Neither Cas nor Dean told each other how they felt for fear the other would not reciprocate. Both couldn’t be furthest from the truth.
Valentine's day was fastly approaching and the looks between Cas and Dean became longer and more frequent. The kids would giggle every time they saw Mr. Winchester and Mr. Novak interacting during recess. Both would blush when they hear the giggling, but never thought much of it.
~~~February 14th~~~
Dean had the kids doing Valentine’s crafts all day and about half an hour before recess, a group of 3 or 4 kids bounced up to his desk.
“Uh.... Mr. Winchester?” the kids giggled.
“What’s up?” Dean said as he gave them a small smile.
“Are you going to make a card for Mr. Novak?” Wide eyes searching Deans face.
“No… It’s.... Uh… Not like that” Dean tries to find any explanation to give these kids, but they somehow drag him over to the craft table to make one anyways. When the bell rings all the kids rush out to play with their friends on the playground. The little ones that made Dean create a card lug him across the field. They reach Castiel and the children hastily whisper, “give it to him.” Dean’s face is a bright red colour as he hands to Castiel, a pink piece of construction paper with little cut out paper hearts drowning in shiny gold glitter that spell out “Be My Valentine”.
The kids tug at Cas’ hands asking him if he had one for Mr. Winchester. Castiel looks at Dean and Dean tries to mouth that it’s okay if he doesn’t have one. He’s telling Cas it’s okay when he always hoped Cas liked him too and Dean thinks his heart couldn’t be more broken than how it is right now. Castiel smiles and pulls a small folded-up piece of paper out of his back pocket and hands it to Dean. The kids run off screaming “We did it! We made them fall in love!” as Dean starts to unfold the little piece of paper.
“I like food other than cookies. Want to get dinner with me some time?” Is all that's on the paper with a little heart drawn next to it. Dean looks up to Cas with a huge smile and hopeful eyes and Dean knows he has the goofiest grin on his face, but he doesn’t really care. They just look at each for a moment before they both start laughing. The rest of recess was making dinner reservations and both Dean and Cas couldn’t have been happier. Dean didn’t stop smiling for the rest of the school day and the kids loved it.