How you meet:
You actually met at Stanford. It was in the boring physics class of Mister Smith.

"Do Physics, physics-" Mister Smith dwelled off. You tugged an strand of your (Hair color) hair out your eyes, trying to pay attention to the class.

"Mister Winchester!" The teacher suddenly shouted making you look up. Of course you knew Sam Winchester. You had heard the story's of the tall man that had suddenly appeared in the school. Mister Smith beamed seeing the tall boy. "You are late" Sam nodded, rubbing his neck.

"I'm sorry. I was calling my brother" Mister Smith nodded before turning to his memos.

"It's fine. Just go sit down next to (Y/N) over there" Sam nodded before making his way over. You quickly buried your head in your notes trying not to make eye contact.

"I'm Sam" You heard him whisper after a moment. You finally looked up and met his large puppy eyes. Your eyes shot downwards towards his books. You frowned, turning the page.

"You were on the wrong page, dumb ass." Sam looked down at his books before a light blush appeased on his face. "It's (Y/N) by the way". He looked up again with a smile.

You meet again:
It had been years since you had last seen Sam. Because you graduated early, your visits became even less. Last you had seen Sam he had been with his girlfriend, Jess. It hurts honestly, loving someone who doesn't love you back.

You turned over the page you were reading before taking a long sip of you coffee. After collage you went back to your home time and found a job as an private investigator. You were currently working on a case about a missing person. You even knew her personally being your hometown and all.

"Do you mind if I borrowed this?" A gruff voice asked before your laptop was taken away of you. "Thanks"

You turned around angry to see a man with dirty blonde hair, green eyes and a leather jacket. He gave you a cheeky smile before the person next to him turned to you.

"Rose Tyler? Isn't she missing?" You nodded.

"Yes she is, may I have my laptop back" the green eyed man just smirked.

"But then why are you searching her?" You sighed.

"I'm a private investigator, dump ass" the man next to him chuckled, finally looking up. Your (Eye/Colour) eyes met his brown ones making you gasp.

"Sam!!" You shot forewards and hugged him. Dean looked as his brother but he just shrugged. Sam finally looked down as you hang around his waist before something clicked.

"(Y-Y/N)?" You nodded, still not letting go. Large arms grabbed you and hugged you back. Dean smirked, seeing his brother all happy.

"So we can barrow the laptop" this resulted in a hit to the head from you.

He lets you stay:
The case was solved. Rose had returned after a year of being missing. Sam and Dean had helped you with the case actually, What surprised you the most was that when you were searching the old burned down factory the boys had pulled out two large guns. When you asked them Dean said it was pest control but when you asked Sam he cracked. He had told you everything about the monsters, demons and ghosts. Apparently they hunted those things. Prevented them from killing people. Or how Dean explained things.

The family business.

You were now in their hotel room reading their dads journal. Dean was still mad at Sam for telling you everything but he look much better now, eating a pie.

"Ghouls?" You questioned looking at Sam. He nodded.

"One in Idaho, a month ago." You nodded before looking back at the journal. Sam watched as you hair covered your face as you read. He never realized how much he had missed you until today.

"Vampires?"

"Not as sparkly as you might think." Dean pointed out from the kitchen. You nodded again before resuming your previous action.

"We are heading to an nest in Omaha next" you looked up from the journal.

"When are you leaving?" Sam watched you with sad eyes.

"Tomorrow morning." Sam saw your eyes widen and the wheels in your head turn. "But we will swap number and w-" you cut him off by standing up.

"I'm joining" Dean shook his head with a chuckle.

"Sorry we don't take little girls with us" you ignored him and turned to Sam.

"I won't follow you on dangerous things but I can help you with research, backing you guys up-" you turned to Dean. "Baking Pie"

"(Y/N) I don-" Sam tried, standing up too but Dean spoke up.

"She does have a point Sam. I mean, this girl bakes one hell of an pie" you smirked and crossed your arms. Sam sighed and rubbed his face.

"Promise you won't try to help?" You nodded immediately.

"Alright, you can stay"

Your favorite quote of his:

"I lost my shoe" how can it not be that one. You were there when he said it and actually he was very glad you didn't touch the rabbit foot.

When he realizes he likes you (friendly):

It was fairly quick after you met. Because he had a lot of school stuff to catch up too you were assigned as his tutor. You were very patient with him and understood when he was late for something.

When he realizes he loves you:

It had been just after the whole demon blood thing. You had lost all your trust in him because of it but after a while you turned to him and said that you would give him a second chance. He knew you would always be there for him even if things turned bad.

His favorite Disney movie:

Frozen. Why, because after a while you started singing let it grow. A parody to let it go about his hair. He thought it was adorable when you danced around him, twirling your hair around.

You take him to Comic Con:

You went as Flynn Ryder and Rapunsel.
Dean went too but as Batman. You and Sam were asked to take a of pictures and people though you were the cutest couple ever even though you weren't.

You break up: (just found out you break up before you even started an relationship, oops)

Angels turned out to be real, who knew? An angel named Castiel had turned up and helped you and Dean save Sam from himself. But lots of angels later and Sam was send to the cage with lucifer still in him. Apparently he was Lucifers true vessel while Dean was Michaels one. Freaky right? Well the Angel Gabriel was supposed to go inside you but he left you alone. Luckily. You had started hunting on your own after Sam left. Dean left for his new family and you had become quite accustomed to the hunting life.

You had just ganked an Djin in Wisconsin. Your new car, a black Chevrolet Camaro. You sighed placing your gun inside the hidden space underneath your seat before sliding inside. You turned on the engine and was about to drive off when your phone rang.  Stopping your action you reached over and took out your phone.

"Hello, (Y/N) speaking"

"(Y/n)" a gruff voice spoke making you sit up.

"Dean?" You questioned.

"Yeah, it's me..." You closed your eyes. Had something happen to Lisa or Ben? Had to right? "(Y/n), he's back" you shot up nearly hitting your head at the roof.

"Dean he can't, he's in the cage" Dean didn't reply. After a moment he gave you an address and said to meet him there.

Finally arriving at the place you got out of your car. Someone have a low whistle. Your turns around to see Dean eying your car.

"Nice" you rolled your eyes at him before pulling him in an bear hug.

"I missed you"

"Same here, Princess" Dean released you after moment or two and you two headed inside the hotel. After asking in which room Sam was you and Dean walked to it. Was Sam really alive? Will he still be the same or- Dean knocked on the door. A scream was heard and you took risks and kicked the door in. What you saw made you wanting to scratch your eyes out.

There was Sam, laying on the bed with an brunet, naked. So he was alive and he hadn't even taken the time to contact you because he was having *** with some slut!!

You turned around and stalked out of the hotel. Dean called after you but you were to angry to care. You and Sam were done.

How he handles the break up:
At first he didn't care because he had really lost his soul but from the moment his soul was back in his body he felt regret like he had never had before. When he remembered what he had done he tried calling you or even tracking you but it was no use, you had left.

Halloween costume:
No costumes. You went in your pjs because you didn't trick or treat. You laid on the couch, cuddling while watching a chick flick movie. Although you already had bought some nice antlers for next year.