You had been the Winchesters friend, all your life. You three had grown up together. So it was no surprise when they called you and asked for your help on a case. Two weeks later here you are, helping out with small things and big things on the case. Sam and Dean both thoroughly enjoyed your company too.
But it had always been your secret crush on Dean that disabled your ability to act normal around him. You had just tripped over your own two feet and he helped you up, chuckling at how clumsy you were. You just laughed and shook off your embarrassment, excusing yourself to take a shower.
Dean's POV
I chuckled as y/n left to her room and shook my head, heading over to the fridge. "You have no idea do you?" Sam asked me suddenly. I was confused, what was I not understanding? I got a beer and sat down.
"What don't I understand, Sammy?" I asked confused as to what he could mean. He just shook his head. "The girl has a major thing for you and you don't even see it. She can barely speak, walk, or function around you, Dean. Face it Y/n has the hots for you." He said nonchalantly. I furrowed my brow. "You're freaking insane, Sam. Y/n is just purely clumsy and that's how she has always been."
Sam sat next to me and shrugged his shoulders. "It's probably for the best anyway. You'd probably fall for her in no time." He said in a challenging tone. Even though I knew it was wrong, I decided to take him up on his bet. "Fine, I bet a hundred bucks that I could date her a month without even feeling a thing." I said knowing this was stupid and probably would ruin my friendship with Y/n.
Reader POV
I got done showering and changing into my clothes. I looked in the mirror and silently told myself not to screw it up. I walked out just as Dean and Sam finished what looked like a serious conversation. "Everything okay?" I asked cautiously. Sam nodded as Dean stood up. "Actually ,y/n, no everything is not alright. I like you and would like to take you on a date."
I stood there stunned, was this a dream? Because there's no way this could be happening. "Shut up, Dean." I said whilst laughing. He shook his head. "Y/n I'm serious! Go on a date with me, I really like you." He suddenly sounded out of breath. Suddenly I smiled and nodded quickly, which made him smile. Maybe this would work out....
