Supernatural Imagines

Dean Winchester Imagine~ Playing Hard To Get

Requested by: The_DrummerGirl

Dean's P.O.V.~

"Woah Sammy, right ahead." I motioned towards a girl who was sitting at the bar a few stool down.

"Seriously Dean?  Could you stop chasing girls for five minutes?" Sam asked me in an annoyed tone.  I gave him a sly smirk and shook my head.

"Nope." I jumped up out of the seat and downed the whiskey I had in front of me. "Twenty bucks says I take her home tonight." I winked at Sam and brought my hand up to his. He looked down at the girl and contemplated for a second before nodding and throwing his hand up too. 

"You're on." Sam spoke towards me confidently. I raised my eyebrows at him and my empty glass back on the table, before walking over towards the girl.  She had long dirty blonde hair that she had pushed out of her face and light gray-blue eyes that seemed exhausted.   I watched as she flipped through a folder sitting in front of her before taking another sip of her drink.

"Hey." I smiled towards her as I sat down on the stool next to her.

"Hello." She continued to stare down at the folder, but had slid it farther away from me.  I looked around at the drunk people attempting to dance and over to Sam who was smirking at me, before looking back towards the girl.

"Uh, mine names Dean." I smiled brightly and nodded.  "Winchester." And as if she knew me personally she raised her eyebrow and closed the folder fast before looking up at me.

"Uh, hey, I'm (Y/N).  It's nice to meet you." (Y/N) turned towards me.

"It didn't seem like it was a few minutes ago?" I told her while giving her a smirk.

"Well a few minutes ago I thought you were a drunk trying to get into my pants, not a Winchester." She stated before finishing off her drink. "Well then again you might still be trying to get in my pants." I winked at her.

"What do you mean a Winchester, do you know Sam or something." I asked her confused.

"Any hunter in the common world knows you two." (Y/N) stated.  I widened my eyes, shocked to see that she was a hunter.  She didn't give off the hunter look, but I should have suspected it do to the tired eyes, the alcohol, and the work laid out in front of her.

"You're a hunter?" I asked her.  She nodded and motioned down to the papers in front of her. "How long have you been a hunter."

"Wait.  I'm going to need a drink before I start talking about this." I laughed at her statement as she as she called for the bartender. "Two whiskeys." She said before she looked over at me and back at the bartender. "Make it four."

"You got it." The bartender smiled at her, ignoring me as he turned towards the rows of alcohol.  He turned back around and handed us the four glasses.

"So, your story." I asked as I began to take a sip of my drink.

...

As (Y/N) went more farther into her life story I began to admire her more.  She was forced into this life, like I was.  Her mother died at birth and her father was killed by a Vampire when she was 15.  Since then she had been on her own fighting the supernatural.  I understood her struggle.  Not getting to actual grow up as a child, treated like an adult from the beginning.  It sucked.

"I'm sorry to hear about your parents." I told her.  I could see that she had a tear brimming at her eye.  I reached forward and wiped it away as it fell.

"Now you see what alcohol does to me." She forced a small laugh as she turned towards the counter. I placed a hand on her lower back as she sat there.  "C'mon, I'm sure you don't want to hear anymore of my story.  Let's go dance." She motioned over to the crowd of drunks.

"Oh, I-I don't dance." I placed my second empty glass on the table.

"You do now, let's go." She grabbed my hand and brought me over to the crowd.  She grabbed one of my hands and placed it on her lower back.  The other hand in hers. She then placed one hand on my shoulder and the other intertwined with mine.  I looked around before I looked back down at her.  Her head landed a little higher up on my chest as she leaned forward against it. I laughed as I heard Bon Jovi: Bed Of Roses, begin to play through the speakers.

"Bon Jovi?" I questioned her. She pulled back and nodded.

"Bon Jovi rocks on occasion!" She argued back.  I laughed at her drunk argument. (You see what I did there?) We continued to dance as I admired every aspect of her.  She held tightly on to me and didn't let go.  After the song finally finished I convinced her to come sit down again.

"I think we should be heading out." I sadly told (Y/N).  She sighed and nodded as she reached for her keys in her back pocket.
"Woah, I don't think so." I grabbed the keys from her hand. "You're too drunk for that. You can stay the night with us tonight, and I'll bring you back to get your car. Okay?" I asked her.  She nodded but then disagreed.
"Wait, is this you just trying to get in my pants?" She asked accusingly while pointing a finger at me.
"No, it's keeping you from dying in an accident or killing someone else. We have extra rooms anyways." I moved her hand down and reached for her folder.  I helped her walk over to Sam who gave me a disappointed look. I leaned forward towards him so that she wouldn't hear me.

"I'm not sleeping with her, she's staying the night, she's too intoxicated to be driving.  I'm bringing her back in the morning for her car." I notified him.  I wasn't going to sleep with her while she was drunk, she seemed to be more than a one night stand.

"Keep the twenty. I think you won." Sam smiled at me as we began to walk out of the bar.

I think I just might have.

A/N~ So let me know what you think.  I think this kind of showed the sweeter side of Dean, which I thought was adorable. So oh my god, I'm watching the Exorcist and I didn't realize how creepy this movie is.  It's the first time watching it and I'm like super creeped out.  Please don't forget to request and let me  know what you think.
Question of the update: Where do you live?

Answer: Michigan.