Ever since that night, you had woken up in Dean's arms every morning. You were unsure what you and Dean were at this point but Sam referred to you both as cuddle buddies which accurately defined your relationship. Whatever was going on between you both, you didn't mind. It was very comforting to feel his stronghold around you. Surprisingly you had been having fewer nightmares since then, but whenever you did he would be there. He knew just what to say to calm you down and never judged or made fun of you.
After a couple of hunts, you decided that a trip to the bar was necessary. You three hit a nearby place that was packed full of different kinds of people. You had your everyday drunks, a couple of bratty college students, and plenty of travelers passing through. You three took a booth as a dark-haired waitress made her way over to you.
"What can I get for you fellas?" she says with a wink towards the boys. You just rolled your eyes knowing at least one of them was going to try to tap that.. most likely Dean which made your blood boil but you tried to hide it. Dean was always oblivious to your jealousy but after you ordered, Sam gave you a look that said he knew and you tried your best to calm yourself down.
"So, who gets the room and who is finding a different place to get their freak on" you state looking between the two boys. You were sharing one hotel room this time so you figured talking it through with them was best before they were too sloshed to effectively communicate.
They both gave you a questioning glance. "Oh come on you two. I can see the way you are looking around the bar. As long as I can sleep in Baby then you two can fight over who gets the room and who has to find a different place to bring their girl"
They looked at each other and pulled out their hands for rock paper scissors. You rolled your eyes knowing Sam was going to win since Dean never changed from rock. Ever. So you went over to find a song on the Jukebox. You finally found one, Let it Ride by Bachman-Turner Overdrive. It wasn't one of your favorites but you were in the mood. You went back to find your drinks had arrived and you three then effectively enjoyed your night.
***Time Skip***
It had been a couple of hours and Dean was flirting up the waitress as you had guessed as Sam and you sat and chatted. "Y/n why don't you just tell him?" he asks. You turn your attention away from Dean and back to Sam.
"Tell him what?" you say taking another sip of your beer.
"Y/n I know you like him and I am telling you he likes you too!" He says scoffing at you. You roll your eyes.
"Yeah right. He is sleeping around with other women because he loves me so much," you say sarcastically. "Sam, I'm no good for him. He deserves someone better," you say looking down.
"Y/n from where I am sitting, there is no one better. Dean obviously likes you and you obviously like him. You two just need to tell each other and stop acting like children"
You look at him and give him a small smile. "maybe" you say.
"Fancy a dance?" a young woman says approaching the table looking towards Sam. You watch as Sam hesitates before saying "Why not" and then you were alone.
You drank for the next while watching Sam flirt with the little lady and Dean making out with the waitress who was off at this point. You were surprised they hadn't left yet. You felt your sad emotions bubbling up as "Please Call Home" played on the jukebox. Suddenly a guy was sitting next to you.
"I see your friends got preoccupied. What douches leaving a pretty girl like you all alone. Mind if I give you some company?"
You look at him. He had soft blue eyes and spikey hair kind of like Deans'. He was a little older than Dean but had a kind face. "You are here already aren't ya?" you say smiling at him. He smiled back.
You learned his name was Jackson, he preferred dogs to cats, loved drinking scotch, had two young sisters that were his world, and aspired to be a vet but never had the money for school so worked as a truck driver. He made you laugh and was nice enough. He bought you shots of whiskey and eventually asked if you wanted to get out of here, to which you agreed. You were super tipsy and leaned on him as you walked toward the door. You saw Sam look up at you from his place at the bar and waved to let him know you were leaving to which he nodded.
You were almost to the door when suddenly you heard an upset Dean behind you. "Where you goin'?" you asked causing you and Jackson to turn around.
"Where does it look like I'm going Dean?" you say a little harsh.
"Y/n you are drunk. You don't even know who this guy is." He says staring daggers into Jackson.
"I know who he is. His name is Jackson and he loves puppies so we are leaving now" you say.
Dean steps forward grabbing your shoulder and turning you back around to face him, but Jackson steps in front of you. "The little lady needs to make her own decision," Jackson says to your defense.
You pat his arm and he moves to the side to let you take to Dean.
"How come you get to go hook up with any slut that looks in your direction, but when I finally have a guy who is genuinely interested in me ask to take me home you get overprotective," you say upset at him. "I deserve just as much 'fun' as you do" you spit.
"Y/n you are drunk. You don't even know what you are talking about" he says pulling you away from Jackson once again.
"I may be tipsy but at least I can still think clearly," you say flicking your arm out of his grasp.
Dean looks at Jackson who had a few inches advantage on Dean, but Dean looked pissed and if looks could kill, Jackson would be dead. "Y/n I really don't think you should be going with him"
Jackson was about to say something but you stepped in, not even thinking about what you were saying. You were just so angry. "Dean it's not fair that you get to hook up with any girl that looks your direction and I can't have a one night stand once a year. Even Sam gets more action than that. Dean, it's not fair that I get to watch you throw yourself at other girls when all I want to do is have a chance with you. Dean, I have loved you for so long but all I will ever be to you is a friend and it kills me." You yell. Maybe you were a little drunk...
Dean just scoffs at you shaking his head. Ouch.
At this point, you realized that most people in the bar were looking at you and you felt angry tears prickling up. Dean completely just blew off your confession like it was nothing and you felt your heartbreak. You knew Jackson wouldn't want to take you home after what you had just said so you just turned around and left. You didn't know where you were going but you were not heading back to the motel. Dean didn't like you and that was fine. You could act like you didn't care though it was devouring your soul from the inside. You just needed to calm down and meet up with the boys later to explain you had a little too much and maybe move on.
It was then you noticed the guy following you. Probably some creep trying to take advantage of the state you were in so you turned the corner and waited for him to catch up. You grabbed him and shoved him into the wall holding your silver demon killing blade to his neck. "Leave me alone you perv." you spit but then you heard the footsteps behind you and suddenly your vision went black.
***Deans POV***
Cindy the waitress was cute and all, but I couldn't keep my eyes off of y/n laughing with that oaf of a guy that had joined her. I watched as several rounds of drinks made their way to their booth and I knew this guy was trying to get lucky and that y/n would be too drunk to say no. Didn't she know better? Not letting guys take advantage of her?
When I saw they were leaving I pushed Cindy off of me and made my way towards them, hoping to stop y/n before they left. I heard Cindy get upset but I didn't care. I couldn't let y/n go with some random perv.
I felt my jealousy rising inside me but I didn't care. "Where do you think you are goin'?" I ask grabbing her shoulder to turn her around.
"Where does it look like I'm going Dean?" she says with that sass that normally sent shivers down my spine.
"Y/n you are drunk. You don't even know who this guy is" I say turning my attention to the dude by her side. I hated him already.
"I know who he is. His name is Jackson and he loves puppies so we are leaving now" she says. Did she really use the excuse that he likes puppies to trust him? No. She is definitely drunk.
I reach out to grab y/n before she turns to walk out the door but this Jackson guy steps in front of her. "The little lady needs to make her own decision," he says glaring at me and I just glare back. I clenched my jaw and felt my knuckles tighten getting upset about this entire situation.
Suddenly I watch as y/n pushes Jackson aside to look directly at me. She looked upset. "How come you get to go hook up with any slut that looks in your direction, but when I finally have a guy who is genuinely interested in me ask to take me home you get overprotective," she asks. "I deserve just as much 'fun' as you do," she says with air quotations.
I wasn't having this discussion with her right here and now. I knew my jealousy was getting ahead of me but I didn't care. I could not see her going off with some random guy I didn't even know.
"Y/n you are drunk. You don't even know what you are talking about" I say pulling her away from Jackson once again. She was not going home with him and that was final.
"I may be tipsy but at least I can still think clearly," she says flicking her arm out of my grasp. I couldn't be mad at her, but I was about ready to kill this Jackson who was still insisting on taking her home.
"Y/n I really don't think you should be going with him" I state in a growl.
Jackson looked like he was getting prepped to punch me so I prepped myself for a fight when suddenly y/n stepped in again. "Dean it's not fair that you get to hook up with any girl that looks your direction and I can't have a one night stand once a year. Even Sam gets more action than that. Dean, it's not fair that I get to watch you throw yourself at other girls when all I want to do is have a chance with you. Dean, I have loved you for so long but all I will ever be to you is a friend and it kills me." She yells.
Did she just say she loves me? Loves? I could feel my heartbeat increase and I wanted nothing more than crash my lips onto hers, but I couldn't wrap my head around what she said so my initial reaction was to let out a scoff. She was drunk anyway right? She didn't mean it.
I watched her expression change from anger to sadness as she walked out of the bar and Jackson just stood there looking at me finally realizing what was going on. "Dude, you are just letting her go?" he asks his voice softening and eyes wide.
I break out of my daze and turn to see Sam standing behind me "Dean she just told you what you have been dying to hear for the past almost two years and you are letting her walk away? Dean, she deserves better. You deserve better. Don't blame this on your 'no-chick-flick moments' because I know you two share more than a couple" He says angrily. I know he was right.
"Come on Sammy," I say walking out to see if I can spot y/n. It was dark and I didn't see anyone walking down the street. "Damn it" I whisper angrily under my breath. I definitely fucked this up.
We hopped into the car and drove around trying to spot y/n and I felt my heart feeling worse and worse for not saying anything to her. I should have just kissed her like I have been wanting to for so long or at least had said something. Suddenly I see an alleyway with some paint splattered on the wall and my heart drops. That wasn't paint.
I stop the car in the middle of the empty street and run out with Sam on my tail. We both pull out our guns as we approach the scene. Y/n's demon-killing knife was laying on the ground next to a small pool of blood and blood and tissues were scattered on the wall closest to it. I felt like I was going to throw up.
"Dean we will find her. She will be alright. She always is" Sam says but I could tell he was trying to convince himself about this as much as me. If only I said something to her this wouldn't have happened. She wouldn't be missing.
"Come on Sam," I say marching back to Baby. I can't lose her.