Dean Winchester One Shots

High School Love

*beep* *beep* *beep*

You groaned as you hit your alarm clock off. You got up and got dressed in your favorite shirt and jeans.

Ugh do I really have to go to school today? you thought to yourself as you started to head down the stairs to join your mother at breakfast.

"Hello Y/N," Your mom greeted you with a smile, "Did you get a good night sleep?"

"Yeah, sure, but I still have to go to school,"

Your Mom just chuckled at you then looked at the clock, "You have to go your going to be late!"

You grabbed your backpack and ran out the door with a Pop Tart still in your mouth. You walked to school with your headphones in playing your favorite singer, occasionally nodding to the beat and humming.

Once you got there you walked to your locker completely ignoring everybody. You took your headphones off when you see your best friend come towards you.

"Y/N did you see the new guy?" She seemed really excited, almost jumping up and down.

"No, why? He's just a new person attending this school, nobody special."

"Well yeah but he's really hot! I mean like REALLY hot! Trust me, you'll like him," She was gushing over this new guy, "Oh look there he is!"

You saw this tall, dirty blonde guy walk towards you, yeah he was hot but you didn't have a chance. All of the girls in your grade were whispering and calling dibs to each other.

"See? Isn't he cute Y/N?" Your friend bumped you on the shoulder.

"Yeah sure," You rolled your eyes and shut your locker.

Well I should go to class and get this day over with

You got to class only to see the new guy in there. He was cute, he had apple green eyes and he had perfect lips. The popular girls were all over him and flirting.

Well this is going to be a long day

You were walking out of your first class but suddenly all of your books fell to the ground with a thud. You looked at the person who knocked them out of your hands only to find it was the new guy.

"Oh um I'm sorry Miss," He instantly got down and helped you clean up the mess.

"It's fine," You mumbled.

You were quickly collecting your books when your hands touched, but he held your hand.

"My name's Dean, what's yours?"

"I'm Y/N," You said shyly.

"A pretty name for a pretty girl," He said quickly but blushed.

"Oh thanks, maybe I'll see you around?"

"Yeah sure but Y/N?"

"Yeah?"

"Would you like to go to the movies with me, this Friday?"

Woah woah what? A really hot guy asked me to go on a date with him?

"Yeah that would be cool Dean!" You said casually but you were internally screaming.

"Good see you then!" He winked then left you with your thoughts.

*Time skip to Friday after the movie*

"Did you like the movie Y/N?" Dean asked.

"It was really good, thank you Dean."

"Your welcome but hey can you hold this for me?" Dean reached out his hand, looking like he was holding something in his fist.

"Yeah sure," You put your hand out but to your surprise Dean intertwined his fingers with yours and kept walking.

Oh you are smooth Dean Winchester!

You smiled and kept walking with him. You both finally got to the Impala and he opened the door for you. You jumped right in then Dean got in.

"Hey Y/N," Dean started.

"Yeah?"

"I know we have only met each other for a week but I really like you and um," Dean looked really shy and for as long as you have known him, he's never shy, "Would you like to be my girlfriend?"

YES!!! you screamed in your head.

"Um yeah I'd like that," You said and smiled.

"Well yeah good," Dean spit out.

You laughed as he drove with you in his Impala down the road.

*Time skip: 5 years*

After a while you both did everything together, and of course Dean had to tell you about the supernatural and The Family Business. He warned you that you could die but to his surprise, you stuck around. You met Sam and you both got along great, he can tell you anything and you can tell him anything. You started to live with them after you got out of high school and helped them with some hunts here and there, but you mostly did the research rather than going out to fight because Dean is really protective over you. Sam and you have always wanted a dog but Dean kept saying no over and over to you even when Sam did his famous puppy dog eyes.

Sam and Dean were out for a hunt and you were home alone so you decided on a episode of your favorite show until they came home.

"That was a quick hunt, you don't even have blood on your clothes," You looked at them up and down.

"Yeah I guess huh Dean?" Sam slapped Dean's back and walked to the kitchen.

"Yeah well Sam and I have a gift to give you Y/N," Dean took your hand and took you to the door, "Close your eyes for a moment okay? Sam will be right next to you."

After a few moments you hear Dean, "Okay open your eyes!"

You opened your eyes and a dog ran to you, "Wait is he ours?"

"Yes but look on his collar!"

You got down on your knees and looked at the dogs collar, attached was a name tag that read: My name is (Y/D/N) and Dean says Will you marry me Y/N?

"Oh my gosh!" You got up and Dean was on one knee and opened a box that had a beautiful diamond ring in it.

"So will you marry me Y/N?"

"Yes!!" You yelled.

Dean put the ring on your finger and hugged you tightly, "I love you so much Y/N."

"I love you too Dean!"

A/N: This was requested by team_free_Will101

I hope you liked it! Also requests are always open so I will take any requests! Don't be afraid to DM me anything you come up with.