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Dean watches too many movies. Ok scratch that he has watched too many rom-coms. Now Dean isn’t really one to believe in the rom-com shit, the joint pining, the miscommunication, kissing in the rain. None of it. He believes it’s a massive bunch of baloney. But a small part of him loves it. He yearns for the joint pining, the miscommunication followed by the kissing in the rain.
The blame for this yearning falls to his best friend Castiel who was the first one to introduce Dean to the rom-com genre properly. Cas loved them so much and at the time Dean was forcing him to watch a bunch of old westerns so in return he allowed Cas to show him the 90s rom-coms he so adores. Then he kept showing him them and before long they had watched almost all of the good ones that were released to the point they were basically caught up with every movie.
Dean always acted like he didn’t like the movies despite the fact he was so clearly paying full attention. Cas never called him out on it, just smiled across at him with the smile that Dean adored.
Now the catalyst for this event all started because of a rom-com Castiel had put on. Netflix in Dean’s own opinions had some of the worst rom-coms in recent memory. He thought they all lacked the charm he found the old ones had. But the one expectation for this was ‘to all the boys I have loved before’. He didn’t tell anyone his love for this particular movie deeming it was far too embarrassing for the captain of the football team to have a secret love for a movie about a girl accidentally releasing a bunch of love letters.
That being said the biggest thing he had taken away from the movie was the way she wrote her letters. The reason she wrote them was that she had overwhelming feelings she didn’t know how to deal with. Something about that had resonated with Dean.
See not only did Dean act like he didn’t like the rom-coms Cas had him watch he also pretended he didn’t have overwhelming feelings for his best friend. Dean loved Castiel more than anything. It’s partially why he let him put on all these movies for him in the first place. He loved to watch Castiel smile and eyes light up when they got the part of the movie he liked.
So taking this knowledge into account he started writing. It started out as something small. Just a short letter telling Cas that he loved him. He never intended to send it much like Lara Jean, he just found an old shoe box, a downgrade of the century but it worked for him.
For a while he didn’t write another letter. But then they sat down to watch another old western one that Dean and his father loved. Nothing happened for the first half of the movie but then he felt a weight hit his shoulder. He looked over at it and sure enough his best friend had fallen asleep on it. He thought about moving him but the weight was nice, Cas was warm.
Needless to say when Cas had finally left for the night Dean had pulled out his notepad again and started writing. This one was more detailed than the last. He had expressed every small thought he had when he looked over and saw Cas asleep on his shoulder. Then he grabbed an envelope, placed the letter inside and sealed it. He hid it away to never be seen again.
But something about that letter had opened a flood gate inside of him. Suddenly instead of one random letter he moved to writing almost one a week, maybe two if they had spent a lot of time together. He didn’t know how to deal with the overwhelming feelings that were inside of him. He had no one to speak to about this, it wasn’t as if he could speak to Cas about it. And he really didn’t want to involve his little brother in his dramatic pining
So he kept writing and before he knew it the shoe box was almost full. He didn’t know what to do with the information, should this be his sign to get over it and stop. Or maybe he should just grab another shoe box. But that felt ridiculous. Dean poured the letters over his bed picking some up holding them in his hands.
“Dean dad said dinner is ready!” Sam said busting into his room hanging slightly off the door, “What are you doing?”
“None of your business” Dean responded, throwing a plushie at him.
“Ok jeez” He rolled his eyes going back out the room not bothering to shut the door.
Dean looked at the envelopes coating his bed and sighed. He quickly grabbed them all, dumping them back into the box and headed downstairs.
He awoke the next morning forgetting all about the envelopes and the existential crisis he was currently going through. Instead he threw on his clothes grabbing the keys to the car off the side and headed out the door none the wiser to what was about to happen.
Dean got to school late as always, quickly heading to his first lesson which was without Cas. He didn’t always enjoy the lessons without Cas not just because his best friend was far better than he was meaning he could get help but also because when they were apart Dean missed him. He wanted to orbit Cas 24/7.
But he got to see him at lunch which meant he had something to look forward to and as lunch rolled around he headed back to his car where he knew Cas would be waiting for him.
Instead though as he headed out the main doors to head down the stairs to meet Cas he got stopped. Turning to see who it was, it was none other than Cas himself. Dean stopped turning to smile his usual charming smile at him only to stop short when he saw what was in his hand.
“Cas?” Dean said, his feet backed away from his best friend ever so slightly.
Castile's thumbs rubbed the edges of the envelope. Dean recognised it almost instantly, every envelope Dean had placed a letter in he had written Castiel's full address on the front in his best fancy cursive.
“Dean” Cas wove the letter up in the air, “Did you mean what was in this?”
“I-” Dean didn’t know what to say all he could hear in the back of his head was ‘why, why why?’ repeating on loop because this couldn’t be happening not now, “I have to go”
Dean turned and ran, not stopping even as Cas shouted after him. He jumped into his impala turning on the engine only taking a quick glance in front of him watching as Cas ran down the steps after him. Something on Castiel’s face made him want to stay but he couldn’t. He had poured his heart into the letters. He had spoken his rawest thoughts and feelings. The idea that Cas had heard him like that he couldn’t stay.
So Dean drove. He didn’t go home, he knew that was the first place Cas would look for him. He didn’t know where to go so he drove to his Aunt Ellen's. The roadhouse was about an hour away from school; it was far enough away that by the time anyone could figure out where he had gone he would have decompressed.
When he arrived she was glaring at him, “Shouldn’t you be at school?”
“Probably” He said hopping onto the bar stools, “I can’t go there anymore”
“Why the hell not?” She asked a look came across her face, “Don’t tell me you go into a fight because I thought we were past that-”
“What no, no nothing like that” He shook his head wiping to hands down his face, “I just I fucked up”
Ellen pulled out some orange juice from behind the counter, placing it on the table in front of him, “Talk to me Dean, what happened?”
“It’s embarrassing” Dean said looking anywhere but as his aunt.
“Well if you don’t tell me I will have to call your father and tell him you’re here” She told him placing a hand on her hips, “So come on spit it out”
Dean looked at her slightly betrayed, “I wrote Cas-” He sighed, “I wrote him secret love letters”
Ellen looked at him blankly before bursting out into laughter. She waved at him, “Sorry- sorry not funny but if they are secret why did you run?”
“Because he somehow had one this morning” Dean exclaimed, “I don’t know how one ended up from under my bed to his hand but it did!”
“And you ran?” Ellen looked at him like she couldn’t understand what she was hearing.
“Yes for the last time I ran” Dean groaned, “I didn’t need to hear him reject me and then explain this is all very weird because I am fucking aware of that”
“Dean” Ellen stated calmly, “Are you sure he doesn’t feel the same”
Dean shrugged. Castiel and Dean had never really spoken about feelings they never saw the need to. They could read each other like a book, Dean always knew when Cas was feeling down because he would go quiet and reserved and when that happened Dean knew to shove on a movie and sit with him till he felt better. And Cas knew when Dean was upset because Dean had the tendency to shut himself off and run. A lot like what he was doing now.
“No” Dean responded after a while, “I don’t but I don’t want to lose him”
“You wont” She stated, “I know that because before you even got here I got a call from him”
As if on cue he heard the sound of a car pulling up to the building and the sound of a door opening. Dean had half the thought to run out the back door and find somewhere else to go hide.
“Don’t even think about it” Ellen snapped her fingers at him, “You will sit there and hear that poor boy out, I’ll be in the back if you need anything ok?”
Dean nodded, eyes fixated on the door. With that she was gone and Castiel was walking through the front door. When he laid his eyes on Dean the boy visibly relaxed.
“Dean…” Cas said, slowly walking towards him. The letter was still in his hand as he came to sit on the stool besides Dean. He placed it on the counter softly, “Can we talk now?”
“Look Cas” Dean said, “You don’t need to let me down easily alright I know what I did was fucking weird”
“I didn’t say it was” Cas interjected, he placed a hand atop of Deans forcing his way into holding it, Cas squeezed Dean's hand, “Do you mean what you wrote in this?”
Dean looked away before nodding quietly, “Dean I need to hear you say it”
“I meant every word Cas” Dean whispered, looking everywhere but at the other boys face.
He didn’t hear Cas say anything for a second only feeling the warm tingly feeling of Castiel's lips giving him a chaste kiss on the cheek. Cas leant his forehead on Dean’s shoulder, “I love you too Dean”
Dean felt as Cas removed himself from his shoulder now sitting back up Dean moved his head to finally look Cas in the eyes. He was smiling at him which turned out to be infectious as Dean couldn’t help himself but smile back.
“I am sorry”
Cas shook his head.
“It’s okay” Castiel said, “I doubt you were expecting to tell me like this”
“You could say that again” He laughed, “Cas?”
“Hmm?” Cas tilted his head to the side as questioning what would happen next.
“Can I kiss you?”
At that question Cas broke into a big smile nodding eagerly at his best friend now boyfriend. To Dean this felt like cloud nine and he never wanted to come down.