Dean Winchester Imagine

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"Hey is (y/n) okay?" Dean asked Sam nervously when he saw you quickly wipe away a tear and walk away to the bathroom. "Her boyfriend broke up with her, over text none the less." Sam replied which brought a smile to Dean's face. "Bout time, he was a dick anyway. She can do so much better." He added. Sam looked down at his brother, "No hitting on her. It wasn't even an hour ago." "I would never." Dean jeered back and Sam gave him a questioning look. When Sam finally turned to face you as you started walking back Dean smiled and shrugged to himself.

The car was awkwardly silent for you. Normally Dean would blast his music or at least try to start up a conversation. You figured Sam had told him to leave you alone because he wasn't talking either. "I'm going to try and get some sleep, wake me up when we're close to the bunker." You say and position yourself to get comfy in the back seat. After what seemed like ten to fifteen minutes, Dean quietly asked Sam if you were still awake. Which you fully were, but you were extremely curious of what'd they talk about if they thought you were sleeping. "Psst (y/n) you awake?" Sam whispered and you kept breathing evenly. "Seems like she's out cold." Sam said still trying to keep his voice low. "So how long do I have to wait?" Dean asks impatiently. Wait for what? Your mind starts making a list of all the worst case scenarios that could make him ask that question. "Dean, it hasn't even been a full twelve hours since the breakup. Plus you don't even know if she would ever want to be with you romantically." Sam adds teasingly. You couldn't believe what you were hearing. It had to be some kind of joke you thought to yourself. They know that you're awake and want to pull a prank. That has to be it. "Sammy I've been waiting for five years for her to be single it's sure as hell worth a shot to try." Dean said said sincerely, and by the tone of his voice you realized it was no joke.

You stared to rationalize everything that has happened between you and Dean in the past five years. You started hunting with them close to six years ago. Your uncle Bobby had introduced you and you three were a great team for that case. Eventually you would meet up with them at cases until one day Dean invited you to live at the bunker with them. Your boyfriend was okay with it, you had been doing long distance anyway,and now he could come and visit you there. He and Dean had never got along, at the time you thought maybe their personalities just couldn't mesh, now looking back on it you realize why Dean didn't like him. Your mind kept going deeper and deeper into memories of Dean being a little over protective of you. Having you room next to him just incase you needed him, how he tried to always keep you in arms reach during a hunt even when you insisted you were fine, how when you were sick he'd stay home cooking for you and watching whatever you wanted to on the couch with you. You got lost in thought and before you knew it Sam, was gently shaking you to wake you up. You did your best to act like you were asleep and upon looking out the window you realize you were home already. "Why didn't you wake me up before?" you mumbled. Dean got out of the car and quickly opened your door, "Seemed like you needed to sleep." He said sweetly offering you a hand to help you out. Sam was already inside the bunker so you got out the car and followed him in, with Dean close behind you.

"No thanks, I'm not really in the mood for going out, sorry Dean." You said and it wasn't lie, but it wasn't why you didn't want to go out. Yes you'd love to go out and be able to drink and maybe forget about your now ex boyfriend, but you were afraid to be alone with Dean. You weren't sure if you felt the same way about him that he felt about you. "Your loss" he said sarcastically and walked out. Sam was sitting on the couch with you, you both were in comfy clothes and ready to just relax. "You know if you need to talk, I'm here." He reassured. "I think I'm just going to try and sleep and try not to cry." You said half joking. You both stood up and Sam pulled you into a hug and whispered in your ear, "You'll get over him, if not we'll gladly go back and kick his ass." You squeezed him even tighter and pulled away,"Thank you Sam. Goodnight" you said walking off into your room, "G'night." He called as you walked away.

It was about 11:30 when you fell asleep and about 1:00 in the morning when you heard a knocking at the door. Your first instinct was to grab the gun you kept in between the mattress and the bed frame, but you heard, "(Y/n) can I come in?" and realized it was just Dean. You sat up in bed, "Yeah come in Dean." you said just loud enough for him to hear. He walked in and pointed to the space next to you at the edge of the bed, "May I?" "You may." He quickly sat next to you and your heart was racing. You were hoping it had nothing to do with him liking you more than a friend. You still would not know how to reply without hurting him. "I realized I never said anything about your breakup." "Dean it's okay you don't have to-" he quickly cut you off, "I know I don't have to. I want to. I don't know the what you're feeling exactly, but I can imagine it, I'm sorry (y/n)." Him bringing the breakup back up brought tears to your eyes and before you could grab a tissue to wipe them away, Dean had his hands on your face and wiped them away. He kept his hand on you for a second after and quickly pulled away when it got awkward. "Crap, I'm sorry I brought it up-" "No it's okay you didn't know." You said trying to blink away the tears. "Look I'm going to be in my room, if you can't sleep and want to talk about other things come in. Or if you just don't want to be alone, okay?" He said as sweetly as possible. "Why wouldn't I want to be alone?" you asked curiously. Dean made a motion with his hand pointing to all the tissues and looked at your pillow seeing the tear stains. "You obviously seem sad, just offering some comfort." He answered innocently. You nodded, "Thanks Dean, night" "I'll keep my door open, night (y/n)". He stood up and walked out of your room and into his. You got comfy once again and fell asleep not too long after.

The next morning you woke to the smell of pancakes. You stretched and slowly got out of bed and walked into the kitchen. Dean was cooking with his back to you and Sam was sitting at the counter facing you. When he saw you he smiled and Dean turned around and smiled quickly before turning back around to flip the pancakes. "Morning sleeping beauty, don't think I've ever seen you sleep that long." Sam said and Dean chucked lightly. "What's the special occasion?" You ask as you walk and take a seat next to Sam. "Thought they might cheer you up." Dean said handing you a plate and a glass of water. You took the plate and placed it on the counter, "Thank you Dean." "Anything for you." He replied quickly and smiled at you.
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Hey guys I'm thinking of making this into a three part thing. What do you think?"

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