Imagine Dean messing up the porposal

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It was a nice fall evening, you were walking next to Dean and wrapped your arms around your torso. You weren't dressed up much, Dean had convinced you to wear this causal sundress, which was cute but not season appropriate, so it was no surprise when the well layered Dean Winchester offered you his jacket out of habit.

You gladly put on the oversized jacket and smiled at him as he took your hand, your other hand going to his pocket, which held a small box. Out of curiosity you fumbled with it, the outside was kind of soft, it was also quite small. You slowly started to open it and the lid felt as though it was fabric. Your finger softly brushed over the content and you felt smooth metal and a stone. It was a ring...

You stopped and your eyes grew. Dean never let go of your hand and when it registered you stopped he turned back to you, concern on his face.

"[Y/n] what's wrong?" He asked as he stepped closer to you.

"Dean... Why is there a ring in your pocket?" You asked as the elder Winchester swore under his breath.

He forgot it was in the coat pocket... He thought he put it in his flannel breast pocket so that this didn't happen. He loved the way she looked in his coat, and knew it would end up around her frame at some point. He was going to walk you to the park, and ask you at the lake while the moonlight shined on the lake surface. He was going to then take you back to the hotel room, which was just for you both, Sam agreeing to room alone, so you both could celebrate. He even purchased a fancy bottle of wine for you, knowing you favored it over a cheap draft. But here you were, in the middle of the sidewalk, with your engagement ring in the coat pocket which your hand was buried in.

"Dean..." You whispered

"I'm such a screw up [Y/N]. You are such a beautiful, smart, caring human being who is one hell of a hunter. You are a hunter's dream, and somehow you settled for me. I ask myself everyday when I see you sleeping in the morning why you would want to be with a screw up like me, I am nothing special. However I also am terrified to lose you, I can't spend another day looking at my phone waiting for the call from you saying you found the perfect man for you. I just love you so much and I want to spend the rest of my life with you. I am sorry you found out this way."

"Dean... I love you too but I need a while to think. Can we just go back to the hotel?"

"Of course." He whispered, terrified that you were going to leave.

You sat on the bed and looked at the comforter, where the opened box sat. You looked at the small diamond ring in the box, it was gorgeous. You thought of your life so far, and what you wanted from it. And as you did you thought of the past year and a half, which had been the time where you actually dated Dean Winchester. However you had known him forever, and knew far more about him then any other person, even Sammy probably. You thought about how he made you laugh when you were ready to cry, how he always encouraged you, the smile he always got when you got him pie or kissed his cheek. You thought of those gorgeous emerald eyes that made you want to get lost and the way that they hid so much pain. He said he was a screw up, but to you he was a selfless hero, and the man you wanted to stay with you for the rest of your life. You slowly reached for your phone and dialed the familiar number. You waited three rings before he answered.

"Hello." Your heart broke as you heard the tears in his voice.

"Dean, I love you." You breathed out

"I love you too."

"I think I found the perfect man." You smiled at the ring as you slowly took it out and placed it on your finger, as you heard him take a deep breath.

"Ok, I can come get my stuff. I hope..."

"It is you Dean Winchester, you are the perfect man for me. I would be honored to marry you, if you will have me."

"Wait what!" He answered

"I love you Dean. I can't picture my future without you, and I am not perfect, and neither are you, but see that doesn't matter. What matters is if we are perfect for each other, and I think we are. I want you Dean Winchester, and I want to spend the rest of my life with you."

You were met with silence... Your heart stopped... And then you heard the key in the door.

Your eyes moved towards the door as you saw Dean throw it open, his eyes finding yours as he tried to catch his breath, showing you that Sam was not right next door. He stepped in the room as you bolted off the bed and colliding with his chest. His arms wrapped around you and held you close as you squeezed him back. He kissed your head as you softly whispered, "So what do you say Winchester?"

"I say, I love you too. And let's do this."

You pulled back slowly and put your hand on his chest, causing a smile to grace his face, and your heart to flutter.

"Babe, aren't you suppose to wait to put the ring on till after I propose?"

"Nah." You responded as he leaned down to kiss you.

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