Dean Winchester One Shots

If You Love Me Let Me Go

~Dean and the reader are teenagers~

It's your first day at your new school, and you are nervous. Will the kids like me? What are they like? Where are all of my classes? What is RTI? Oh no.

You walk down the halls looking down, trying not to make eye contact. You look up for a quick second and you see a couple of girls walk towards you.

"Hello, I'm Kady!" The girl with the long brown hair yells at you.

You internally groan but politely respond, "Hey I'm Y/N!"

"Nice to meet you, do you need help getting to your classes? It's really confusing here,"

"Yeah, yeah that'd be nice," You smile. At least you have a friend, well, maybe.

Kady showed you all around, the building was huge but it was very nice. You both had all of your classes together, even your favorite class.

Once you both went to lunch in the huge common area with kids that yell at each other over the noises of the kitchen. As you sat down one boy was looking over at you. He was very attractive, well that's not even a good word to describe his beauty. He has dirty blonde hair and bright green eyes, he had a nice flannel shirt on and plain dark denim jeans. He looked pretty clean unlike the other boys in the school.

"Who is that?" You ask Kady.

"Oh, that's Dean Winchester,"

"He's pretty cute," You shrug trying not to sound like a fan girl.

"Yeah I guess, he's been in this school only for a month. Nobody really knows much about him, only that he takes care of his little brother and he drives an Impala '67 all over the place,"

"Oh," You say quietly and look down, ending the conversation about the mysterious Dean.

After lunch was over you walked to your locker to get some books for your English class as you feel a tap on your shoulder.

"Hey, miss what's your name?"

You turn around quickly to see Dean right next to your face, "Oh hey, um"

"You don't have a name huh?" Dean chuckled.

"Oh sorry, I'm Y/N" You smiled shyly.

"Well Y/N, how about going on a date tonight?"

"What?"

"I said, you me a date tonight?" Dean laughed.

"Oh yes, sure," You stammered a bit shocked, but happily agreed to the date.

"See you tonight Y/N," Dean winked and waved goodbye.

You stood by your locker shocked, that was awkward but hey you got a date.

~Le time skip to date~

"Y/N, can you guess where we are going?"

You looked out the Impala's window for a while before answering, "I have no clue,"

"Good," Dean smirked before pulling down a back road.

You watched him, he smirked as he drove. He'd whistle to his old rock music and sing along.

"So, what's your back story?" Dean asked.

"Oh well, I don't really have one. My parents got a job out here, so we were forced to move. I was raised in a small town, there wasn't even a fast food place there or really anything. It was quite boring and the people there were, well you know, pretty much assholes to me. I wish I could've brought my best friend," You looked down remembering your best friend.