Author's note- Ha-ha I am starting another story and I am taking a completely different route with it. Updates might not be too frequent because I am juggling school with this and grades are my first priority. Also, I know Jess doesn't go to Chilton in the show but he is going to in my story and if you have any flames then get over it because you read the summary.

Summary- Rory Gilmore, your average teenager at age 16, is heading off to Chilton... with her best friend Jess. Together they will discover the trials and tribulations of love, life and fitting in. Something they never had to deal with at SHHS.

Chapter 1- shiver

~You build me up

you knock me down

Provoke a smile

And make me frown

you are the queen of runaround

you know it's true~

(Maroon 5- Shiver)

"Remind me why we are doing this again." Those were the first words to escape Jess's lips that sunny Monday morning that we began our careers as Chiltoners.

"Cause this is what smart people do." I joked; pushing him off the bed and plopping down on it, the slight moan that he released reassured me he was ok. Not that I was expecting him to not be because we go through the same thing every morning. Except this time, we were actually being waited on. In fact by a bunch of people my mom, Luke, my grandparents, Patti, Kirk, my dad...

"Why do we have to wear this tacky uniform?" Jess asked to no one in particular, causing me to look up. I cracked a smile at Jess, watching as he tangled himself out of the shirt and slipped it on correctly, finishing off the ensemble with a run of his hand through his coal black hair.

"Ready?" He asked finally, grabbing his keys.

"I have been waiting on you." I reminded him, easing myself off the bed.

"Well sheesh, you could have just left without me then." He mocked, causing him to receive a pop on the head.

"You would have never made it if I hadn't come over and waited. Besides you have a car and if I went by myself the Chilton my mom, my grandmother, my dad, my grandfather, Luke, and all of them would have ended up following me there." I said.

"Well nobody could ever say that all the attention has gone to your head." He said sarcastically, as we entered the diner.

"Oh Rory honey, you are going off. Are you sure you don't want me and your grandfather to give you a lift there? I mean we do have ties at Chilton." My grandmother said, looking up at Jess who was getting coffee and flipping the pocket knife that was on his key chain and grinning off in space. A slight wince told me what this was all really about. I smiled slightly and turned back to grandma.

"He is a very careful driver." I replied, lying through my teeth. He wasn't reckless but careful wouldn't be a way I would describe it either.

"Rory we got to pull out of here now. Hate to break up the party as we sail away into the unknown territories." He said, handing me a cup of coffee and pulling slightly on my sweater.

"Sorry Grandma, you know how it is." I said, swatting Jess's hand away.

"I suppose, I will see you Friday then." She said curtly, though I could tell her feelings were hurt. I sighed, taking a long gulf of coffee.

"Rory!" my mom cried, shaking my shoulders the coffee that I had just sipped threatening to spurt out of my clasped lips.

"Never shake a Gilmore on her first sip of coffee." I said, looking up.

"Right I forgot but my baby's going to Chilton." She said, singing the end of her sentence.

"Yea and if I want to get there I got to go but I will call you at the Inn when I get home, bye mom." I said, giving her a slight hug and running out the door, my backpack fluttering through the door as it closed behind me.

"This looks like a dungeon of distress." Jess said as soon as we got out of the car. The morning sun casting a shadow over part of the building; I tried to remember what the certain times where that a shadow cast on the east side but got nothing. I sighed and began to wonder if I was really cut out of this place. Realizing I hadn't answered Jess and a little irrated at him, I tried to keep the conversation flowing.

"You really are one for first time quotes." I muttered, remembering what he said this morning. Laughing, I took another swig of my coffee and tossed it in the bin, missing it by like three feet. Sighing, I picked it up and placed it in.

"With a shot like that you should try out for the girl's hoops team." He said sarcastically.

"With an ass like yours you should go to Hollywood and become a Calvin Kline model." I retorted.

"You been checking me out Gilmore?" he asked, slinging an arm over my shoulder.

"If by checking out you mean trying to move my way around a big blob of fat then yea." I joked, sliding out from beneath his arm.

"That was cold." He said, pushing me slightly. I stumbled, laughing that I had gotten him speechless for once, and not paying attention. I bumped into a group of people, someone falling smack dab on top of me.

"Jess I am going to hurt you so bad, it won't even be funny when I do." I muttered, noticing the slight cut that was continuing to bleed down my wrist and

"Can I help you up?" a deep voice asked, his hand outstretched.

A/n- let me know what you think plz!!!! They will get longer to by the way. IcAnCu