This imagine was requested by @jessicaboobear

Her name is Jessica so instead of the usual Y/N I will use her name. Hope you guys like it!

Imagine: Being friends with Dean in high school and years later you guys meeting up again and sparking some new feelings.

~~In High School~~

You woke up Monday morning dreading the school day. You rolled out of bed and got dressed for school. "Just a typical Monday morning," you said finishing getting ready. You were 17, so you already had your own car and drivers license. You took your car, a Pontiac Firebird. When you arrived to school, you were greeted with your best friend. "Hey Jessica," she said. "Hey," you replied.

You guys walked to the entrance of the school and went inside. As soon as you guys got inside, you realized that something was different. All of the girls were in a group staring and giggling. Some guys were also staring too, some giving death glares. At the center of it all were two boys. One was older and really cute and the other was younger, he seemed cute too, but he was too young for you.

Your friend stopped and stared at the two boys. After a while, you had to pull her away. You weren't one for big crowds. A few minutes later, the bell rang. You walked to your first class: Biology. When you walked in, you saw the older boy from downstairs talking to a bunch of pretty girls. He was flirting with every single one of them. You scoffed and went to your seat. You hated players.

A few minutes after you sat down, your teacher came in. "Hello class," she said. "Good morning, Ms, McKenzie," most of the class responded. "Today we have a new student," she said motioning for the boy to come up. He did as he was told and went to the front of the class. "Why don't you tell us about yourself," she told him. He nodded his head and said, "Well my name is Dean Winchester. I came her from California, I was born in Kansas, and I have a little brother, Sammy, who is a freshman."

All of the girls melted when he talked and he walked back to his seat. The teacher tried to continue with the lesson but half the class, the girl half, wasn't paying attention. Oh no they were far too busy paying attention to Dean. "Alright that's enough. Dean why don't you go take a seat next to Jessica back there," she said pointing to you. The whole class looked at you, and you quickly looked down.

Dean sighed a little and moved all of his stuff next to you. He sat down and winked at you. You felt a small blush rise to your cheeks. You quickly focused your attention back onto the lesson. "So your Jessica, right?" he asked you s few minutes later. You nodded your head and said, "And your Dean?" He smiled and said, "Oh so you've heard of me." He got a smirk on hid face and you said, "Yeah you introduced yourself to the class," you said chuckling.

Dean smiled a bit and said, "Oh. Right." The whole class Dean kept trying to talk to you, and you tried to ignore him while still being polite. Finally the bell rang. You and Dean both stood up and gathered your things. "You know Jessica, you aren't like other girls. You're different," he said. "Different good? Different bad?" you asked wanting clarification. He was about to answer when the teacher yelled, "Quiz tomorrow on the lesson we learned today!" Dean cleared his throat and you finished gathering your things. "Guess you were saved by the teacher," you told Dean smiling as you left the classroom. You could feel Dean's eyes on you as you left.

The rest of the day seemed to go by pretty fast, and the next thing you knew, it was already 9:00 PM. You yawned tiredly and decided to go to bed. For the first time ever, you were actually excited to go to school tomorrow. You woke up the next morning and got ready. You did your same daily routine and then left for school. When you got there, you best friend again greeted you, and when you walked in the school, you immediately saw Dean with about thirty girls surrounding him.

You walked past him, locking eyes with him for a few moments, but you quickly looked away. You got to your biology classroom and sat down just as the bell rang. Dean soon came into the classroom, with the mob of girls behind him, and took his seat next to you. "Morning Jessica," he said. "Good morning Dean," you replied with a smile. "Ready for the quiz today?" he asked. "I think so," you said. You had been up all night studying for it. "Are you?" you asked him. "I hope so," he replied.

A few moments later the teacher came in and started handing out the quizzes. The whole class finished the quiz in 20 minutes. Then the teacher decided to grade the quizzes in class. You got your paper back and you read the grade. 100%. You smiled to yourself and Dean looked at you. "Good job Jessica," Dean said. You smiled and said, "Thanks." You looked at Dean's paper and he got a 54%. "Hey if you ever need some help in the class, I could help you," you told him.

His eyes lit up with excitement. "You would really tutor me?" he asked youm "Yeah, why not?" you replied. He smiled and you guys made the plans for your first tutoring session.

~Present Day: 10 yrs. later~

It has been 10 years since you graduated from high school. Senior year was your favorite year. It was the year of your best grades, the year you won Prom Queen, and the year you met Dean Winchester. But it also happened to be the year your family died. You came home from work one day in the summer. It was about 8:00 PM. You opened the door to your house and walked inside.

You went to the kitchen and when you got in you saw your parents on the floor dead. With their hearts ripped out. And their killer was still there, as if he was waiting for you. You grabbed the first thing you could find for protection which happened to be a silver knife. The attacker came at you and you stabbed him in the arm. The knife seemed to have hurt him more than it normally would have and the attacker left.

After a lot of research you found out that the thing that killed your parents was a werewolf. Now you were a hunter, and a damn good one too. You were on a hunt in Michigan. The victims were all college students at the same college, so you decided to pose as a college student. You got to the college wearing an ACDC shirt and skinny jeans with some tennis shoes. You even thought you were going to college there. You went into a fraternity where one of the victims deaths was. It was an all girl fraternity. You were looking around when you heard someone say, "Excuse me miss, but can we ask you a couple of questions?"

You turned around to look at the men. They showed you their IDs and one of them said, "I am Agent Phillips, and this is my partner Agent Rogers. We need to ask you a couple questions about your friend, Kelsie Smith. The one who was murdered." The man who was talking was gorgeous. He looked to be your same age, and you couldn't help but stare at him. His partner was a giant. He literally towered over you. "Okay," you told them.

They went to sit down on one of the couches in the main room of the fraternity and you followed. You were kind of nervous, because you were only posing as a college girl. You weren't really one, and you didn't know the victim.

"Did Kelsie have any enemies?" the tall one asked. "Not that I know of," you told them. "Has she been acting kind of strange before she died?" the cute one asked you. "Look, I am not exactly the right person to ask here. Kelsie wasn't exactly one of my closest friends. I would ask Sandra Smith, her twin sister," you said, standing up and the tall one said, "Wait, wait. One more question. Have there been any cold spots lately?" You looked at the two men and said, lowering you voice, "Agents are you...hunters?" you asked them.

They looked at you with a strange look and the cute one said, "Yeah we have hunted before, you know deer, sometimes elk." "No agent I mean the type that hunts monsters and demons," you said. Both of the men stood up and gave you a small smile. "You're a hunter too?" the tall one asked. "Yep," you replied. The cute one nodded his head and said, "I am Dean, this is my brother Sam."

"Wait Dean...Winchester?" you asked. "Yeah, how'd you know?" he asked back. "It's me, Jessica, from high school," you told him. Dean got a big smile on his face and pulled you into a hug. "It has been too long Jess," he said. "I know," you replied. "Wait Jessica, what happened? Why are you a hunter?" he asked concerned. "A werewolf killed my parents," you told him.

Dean pulled you into another hug and apologized. "So you wanna work this case together?" you asked the boys. They nodded in excitement, and you smiled. After questioning a few different people, Dean and Sam took you back to their motel room since you didn't have a place yet. You spent the whole night talking about the case. However, Sam had to do most of the research, because you and Dean were very busy staring at each other.

At the end of the night you had all decided it was a spirit. The ghost of Ted Goodacre to be exact. Ted founded the college, but when he died, three weeks ago, 3 adults and 3 students who were on the school board changed the way the school was when Goodacre was alive. The three adults were killed in a car accident and there was only one student still alive: Evan Rogers.

Sam, Dean, and you all rushed to the fraternity Evan was in. It was 11:00 at night when you got there. You knocked on the fraternity door and a tall blonde man opened it. "Hi we need to speak to Evan Rogers," you told the man. "Under what authority?" the guy asked. Dean and Sam pulled out their FBI IDs. The blonde man held up his hands and said, "Woah man I was just joking." "Yeah, yeah. Where's Evan?" Dean said. "Upstairs. First door on the right.

We rushed to his room and when we knocked on the door, an average sized blonde man opened the door. He had glasses and was kind of scrawny. "Are you Rvan Rogers?" Sam asked. The kid nodded his head and Sam, Dean, and you went inside his room. "What's going on?" he asked. Sam told Evan everything about Ted Goodacre, as Dean made the salt circle. You pulled out tge three shotguns filled with rock salt and gave Evan an iron bar to use for protection. "Alright Sammy, Jessica and I will stay here with Evan you go find ol' Goodacre's bones and salt and burn them," Dean said. Sam did what Dean said and left.

Soon after Sam left, Ted, well Ted's spirit, appeared. He came after Evan and you shot him with rock salt. He appeared again and Dean shot him this time. This went on several more times, and each time, Ted's spirit got smarter. The next time he appeared, it was right behind Dean. He knocked Dean's and your's guns away. He then threw Dean against a wall and Dean was knocked out for a few seconds. You ran to grab your gun, but Goodacre was fast and threw you with a flick of his fingers. He ended up throwing you out of the two-story window. "No! Jessica!" you heard Dean yell.

You landed on the lawn in front of the fraternity. You got the wind knocked out of you and you couldn't move or breathe. A few seconds after your fall you looked to Evan's window and saw an orange light come from it. Sam did it. He found Goodacre's bones and salted and burned them. About a minute after Goodacre went up in flames you saw Dean running towards you. "Jessica? Jessica are you okay?" he asked coming over and scooping you up in his arms.

"I think so," you told him. "I thought I lost you," Dean told you. You smiled a weak smile and said, "Can't get rid of me that easily." Dean smiled back at you and said, "Jessica, I never want to come this close to losing you again. I, uh, I never told you this, but ever since I met you in Biology class, I have loved you. I fell even more in love with you everytime we had a tutor session, and after graduation I kind if just buried those feelings because I never thought I would see you again, but when I did all of those emotions just came back, and I just really wanted to tell you that I love you. I am in love with you Jessica."

It took a minute for you to process what Dean said, but once you got it all down, you smiled at Dean and said, "I love you too Dean." That was it, those 5 simple words. Still those 5 words filled Dean's life with so much hope, and love. He pulled you into a sweet, slow, passionate kiss. You immediately kissed back, completely in love with Dean. When you both pulled away you could see the happiness in both of your eyes, because for the first time in a long time, everything was perfect.