Dean Winchester x Reader One Shots

⚠️ The Proposal ⚠️ (THE WEDDING SERIES)

"Sam, can I talk to you," Dean asked his brother as he lingered in the doorway to his room. 

Putting the book he was reading down, he gave Dean his full attention.

"Yeah, sure."

Dean slowly walked inside, head turning in all directions to make sure that you weren't around.

"You okay Dean?"

With a sigh, he sat down next to his brother on the bed. He began fiddling with his fingers, head kept down like he was embarrassed to ask his brother for help. Dean didn't know who else to go to for this kind of thing. He never thought that this idea would pop into his head but here he was. This was a huge step in the older Winchester's life. To say that he was nervous was a damn understatement. He wasn't sure if he should do this or not. Cold feet was a real fucking thing he guessed and he hadn't even asked you yet. 

"Dean?"

Dean quickly looked at Sam, almost laughing to himself, then looked away. He cleared his throat. It was now or never. He needed to ask him this before he said fuck it and walked out. 

"I um...shit Sammy this isn't easy for me to ask."

"Take your time. I'm all ears when you're ready."

Dean sighed, mentally slapping himself. "Okay...well...you know that (Y/N) and I have been together for a long time and I...there's something that I want to ask her but I'm not sure how."

"Is it bad?"

"What?! No! It-" Dean cut himself off, standing up to begin pacing. 

"Dude I can't help you unless you tell me what's going on."

He stopped, hands on his hips as he glared at Sam. Calming down after a couple deep breaths, he finally came out with it. "Sam I want to ask (Y/N) to marry me."

Sam's eyes widened. "Are you serious?"

"As a heart attack."

Sam was speechless.

Running his hands down his face in frustration, Dean continued. "Sam I want to marry her. I know that with what we do I probably wouldn't have the apple pie life but I don't care. I love her. This has been on my mind for the past four months. I want to at least try to be happy with someone. I um...I enjoy coming home to her. I love how she's always around, waiting for me to walk through the door of the bunker. I mean you've seen how her and I are with each other. She loves me too. She's never asked me about anything when it came to the subject of marriage but I want to do this Sammy. I can't think of nothing else I want more than this."

The younger Winchester still couldn't find the right words to say. He was shocked that Dean wanted to do this at all. He's known his brother a very long time and he never ever imagined him settling down with anyone. 

"Please say something Sam. Am I making a mistake?"

"No Dean I don't think you're making a mistake."

"Then why are you so silent?"

"I'm just...processing everything."

Silence fell between them at this point. Dean didn't want to leave and Sam wanted to give him pointers of what to do going forward with this. 

With pleading eyes, Dean asked, "Sam you gotta help me with this. I don't know the first thing about going out and buying a ring or how to chose the right one. Also where do I take her to pop the question? Do we go out to dinner? No there would be too many people around. Do we go for a walk in the park? Do I ask her here in the bunker? Come on Sam help me out here."