Thank you for reading this! I will try and update as much as I can, weekends will be easiest. If you guys have any ideas for me, I will take them into consideration. Enjoy the chapter!


The two of them went outside every recess together. After lunch and after Castiel would help kids put on their hats and gloves, Dean would go outside and sit next to Castiel on what they designated as their bench. Usually Dean would bring some food along with him for him and Castiel. Dean would always bring himself a slice of pie and would bring Castiel a couple of oatmeal raisin cookies (which Castiel had off-handly said was his favorite) and both of them some coffee. Castiel had also joined his group of coworker friends who, when Castiel was getting them something or looking after the kids, joked that him and Dean would be a cute couple. Dean always scowled and tried to look mad, but in reality, he wished him and Cas were a couple.

In his class, his kids were making Valentines. Dean tasked them to give them to people who they don't talk to much and maybe have them make some new friends. Dean was supervising when he felt a tug on his jacket. "Mr. Winchester?" A small voice asked. It was Claire, one of his personally favorite students.

"Yes Claire?" He stepped down to her level. "Do you need help?"

She shook her head. "I was just wondering if you was gonna make a Valentine for Mr. Novak." Dean immediately blushed. "I mean, you like him, don't you?"

"Mr. Winchester, you sit next to him all the time." Ben pointed out. "Are you in looooovvvveee?"

Dean could feel his face heating up more by the second. He cleared his throat. "I'll make one if you guys help me."

Dean's small class cheered and abandoned their projects almost immediately. Claire grabbed three sheets of red and pink construction paper and the glitter glue. Ben started cutting out paper hearts and gluing them to Claire's construction paper. All of the other students stuck stickers and foam letters on the large, over-glittery card. When they were done, they showed the card to Dean.

It was one full sheet of paper, with foam letters that spelled 'Hapy Vallentins Day' and covered in little, crooked, cut out hearts. Glitter glue formed a border on the outside. Lucas drew what looked like Dean and Castiel sitting on the bench outside at the bottom. Dean smiled at his students, but then felt his heart sink as the bell rang for lunch.

Castiel was waiting outside on the bench when Dean came outside. He tilted his head in confusion when he was followed by what looked like his entire kindergarten class. A little girl named Claire was leading the group with something in her hands behind her.

Dean looked down at the ground sheepishly as the kindergarteners giggled. Claire reached out her small arms and gave Castiel a large, overly-decorated card. Castiel looked up at Dean, whose face was beet red with embarrassment.

"Mr. Winchester wanted to give you a valentine." Claire explained. Her face turned a sadder expression when she didn't see Castiel attempt to give Dean a card. "Do you have a card for Mr. Winchester?" She asked, her voice almost cracking with sadness and disappointment. "Don't you like him too?"

Castiel looked at Dean, who was trying to mouth to him that it was okay; that he didn't need to give him a card. Castiel shot him and small smile and stood up, reaching into his pocket and grabbing a small, folded piece of paper. He handed it to Dean, feeling his face turn red as he took it.

Dean's class moved out of his way as he unfolded the paper. In beautiful, curly handwriting, Castiel wrote You know, I do like more things than oatmeal raisin cookies and coffee. Why don't we go get dinner sometime? with a heart drawn underneath.

Dean looked up at Castiel, who was trying not to look at him. When Castiel finally did look at him, Dean mouthed to him yes.

Dean's class all giggled and went their separate ways, no longer wasting their recess now that they'd gotten what they'd come for. "You actually want to go out with me?" Castiel asked. "I wasn't sure if you were gay, so I was almost not going to give it to you-"

"Cas, I said yes." Dean laughed. "Why are you freaking out so much?"

Castiel sighed. "No one's really ever said yes to me before." He mumbled. "I thought you might have just been joking so your class would leave you alone."

He sat back down on the bench with Dean plopping down beside him. "Well, just to calm your nerves, I meant it when I said yes. When do you want to go?"

"I'm free tomorrow night." Castiel said, obviously not used to planning a date. He seemed so nervous that Dean wasn't serious and Dean wondered what happened to him for him to have such a small trust bubble.

"That works for me." Dean replied. "I'll pick you up at seven?"

Castiel nodded. "Okay."

After recess that day, Dean went to Charlie and told her about what had happened. "Oh. My. Goodness. You're kidding!" She exclaimed. "He asked you out?" Dean nodded. "It was bound to happen sometime."

"What's that supposed to mean?" Dean asked.

Charlie rolled her eyes. "I've seen the way you two look at each other during our little get-togethers in the teacher's lounge." She grinned. "Now Jo and Kevin owe me twenty bucks each."

"You guys were betting on this?" Dean groaned.

"Yeah. I bet that one of you would ask the other out on or before Valentines Day, Kevin bet that it would be sometime next week, and Jo thought you two would take over a month to confront your feelings." Charlie confessed. Dean crossed his arms. "I'm sorry!" Charlie said. "But you at least have to tell me what, when, and where."

Dean sighed over-dramatically. "Okay, fine." He said. He actually was happy to be talking about this with Charlie because he knew that she actually cared to talk about this, unlike Kevin and Jo. Kevin just plugged in his earbuds and tuned him out and Jo acted like she cared, but she wasn't the girly-girl that you'd assume she'd be. "I'm going to pick him up at seven tomorrow night and I think I'm just going to take him back to my place and make some food."

Charlie raised one of her eyebrows. "Oh." She said coolly. "I see."

"No, Charlie." Dean face-palmed himself. "That's not what I mean. You know that's not what I mean. I really like him and I don't want to mess this up for what could possibly be a serious relationship." He sighed.

"You won't and you know why?" Charlie asked. Dean looked at her. "Because you're Dean fucking Winchester!"

"Charlie!" Dean said. "We are at work."

"This is the teachers lounge, Dean." Charlie said, rolling her eyes. "No impressionable youngsters are here."