A/N: This story is about Sam's life before the pilot, What happen that night after the fight he had with John. Sam couldn't take it anymore and had to take some drastic action that could change his life and Dean's forever. Please note there are some Gilmore Girls stuff added into this and it's a bit of AU. :)

Disclaimer: I do not own anything from Supernatural or Gilmore Girls. The only thing I own is my character Jenessa, Dean's daughter and Nicole because they are mine :)

Sam Winchester had always wanted to have a normal life, free from hunting and the supernatural since he was four-teen years old. There has been times over the years he and John had gotten into fights over having to move from town to town, living in rental houses and motels. Going back deep into Sam's life, he was only six months old when his mother, Mary was killed in a fire on November 2, 1983. Since then John had been trying to get revenge on the thing that killed her. His older brother Dean was mostly left to raise Sam when he was only five.

Then in Summer of 1996, Dean was only seventeen at the time when he met a girl from the school he was attending at the time. The two had been going out for a couple of weeks leading them to take it to the next level. Couple months later, Dean gets a call then later finds out that his girlfriend Nicole, was pregnant. They decided not to tell John about the pregnancy but Sam was told right away by Dean. Four months later, Nicole's parents found out and contacted John. He was livid..and there was a huge fight between Dean and him, He wasn't punished or anything it wasn't gonna do any good but they had to figure out how to raise his daughter.

Nicole decided to let Dean have the baby but does have visits from time to time. After the baby was born John finally learned to accept that Dean was a teenage father and helped him with the baby while trying to hunt. That was three years earlier. Dean nor John was ever ready for what was about to come next.

Sam did love his father even though the man cared more about hunting monsters out there..He wanted to protect the boys at any cost to. One night when Sam was only seventeen, He told Dean then his dad that he had been accepted to Standford with a full ride.. That didn't go well with John, causing a major blow out. This fight caused Sam to run out of the house and never return. It didn't help matters when John told him if he leaves he should stay gone.

A couple days after Sam had fled the house he was in a motel room watching TV and thinking about what had transpired between him and his dad. Nothing good ever came from hunting he thought. He had to do something..He stood up pacing back and fourth a bit in the room. He takes a deep breath pulling out his phone looking at the list, Finding Dean's he waited for a few minutes, then dialed his number. Dean answered the call after two rings. Sam was glad to hear his brothers voice..He was so close to him, He loved Dean with every being in his body.

Dean was happy to have heard Sam on the line he stood up from the kitchen table going into the other room to speak "Sammy, Hey buddy..I've been so worried about you, I know what happened the other night was bad gotta come home..he didn't mean it."

Sam sat on the side of the bed rubbing his eyes and sighs deeply "That's the thing Dean, He did mean it..I want to come home but I can't..I've been thinking..about things. I have to go away for awhile..

Dean felt alarm bells going off in his head he knew something wasn't right what did Sammy mean going away for a while he clears his throat to speak "Sammy? What are you talking about. I mean if you need some space thats fine but..

Sam sighs before speaking "No, Dean Thats not it..You might like what I'm about to do..but I'm telling you this because you're my brother and I love you. Just please don't tell dad okay" Sam could feel his head pounding all he wanted was some kind of freedom, Away from the hunting and the drama.

Dean paced back and fourth for a moment then spoke" Sammy, you're scaring me man, Listen I won't stay anything to dad but you gotta tell me what's going on, What are you about to do?" Dean was panicking inside and worried for his baby brother. He sighs going down the hall into the bedroom hoping that Sam doesn't do anything rash.

Sam was quiet for a moment then decided to speak "Dean, I'm not trying to scare you. It's just, I need to vanish for a bit from everything, this life and "Sam had paused for a moment before continuing" I promise I'll will give you the heads up on where I'm going, just please don't tell anyone even dad,

Dean rubs his eyes and pinches the bridge of his nose before speaking "Sammy, I don't like the sound of this. What about Standford? the collage you got accepted to? You know the entire reason why you had the fight with dad?

Sam rolls his eyes at the sarcastic tone Dean had and spoke "Yea I remember I was there during the fight, "He inhales a deep breath before speaking" Dean, don't worry about Standford. I can figure it out, Please Dean I need to do this.

Dean sighs even more before speaking "Sam, Alright, listen if I agree to this and I said "IF" There gonna be some conditions, I want you to call me and let me know where you are and if you're okay, I want updates on whatever or where-ever you're at. You can vanish from dad and the others but, I'm not gonna let my baby brother vanish from my life, Understood?

Sam chuckles hearing Dean laying down the rules he gets up getting a can of soda popping it open then takes a sip from it before speaking "Same ole Dean handing down rules, you know I thought you'd be tired of that by now. "He pauses for a moment before continuing" Alright, you got a deal Dean, I don't know where I'm gonna go yet but..I'll keep you updated.

Dean rolls his eyes at the rule comment and nods his head while listening to him on the phone "Good, I am glad to hear that. Sammy whatever you do out there remember you are still a teenager and this world is a crazy place, I'm not just talking about monsters either, There are people out there that are..You gotta watch your back okay?

Sam smiles some at Dean's concern and sighs "Yeah, I know and I will You don't have to worry about me Dean I know I'm seventeen now but I can handle things out there plus I still have protection if I need it.

Dean rolls his eyes hearing him and smirks a bit "Protection? Well that's good if you ever meet a girl you wouldn't want to get into the same trouble as I did when I was your age " Sam had to roll his eyes at that comment. Dean spoke up again after chuckling a bit to himself "I'm teasing you Sam, Be careful out there bro, Call me soon alright?

Sam inhales deeply and spoke "Yeah I will Dean you have my word on that." Sam said bye to Dean then sat down at the round table getting his laptop out, booting it up, While browsing the net he kept thinking back to the fight in his head. It was horrible he thought to himself plus he never thought he'd use the language he had done that night in all his life. Dean is right though, He was still a kid, planning a life on the run. He sat up in the seat after seeing a town that stood out to him, Looking it up he smiled to himself and realized where he was gonna go. "Stars Hollow" He muttered to himself.

I hope you had enjoy reading the start, Next Chapter will talk about how he arrives in Stars Hollow, people that he met and whim finding his first love. Please note this story does contain Gilmore Girls in it though I placed it in Supernatural category because it's building it up before the pilot.. Sam's life before the series, I do hope you enjoy where this is going. Reviews and suggestions are welcomed :)