Disclaimer: if i owned the rights to the gilmore girls do you really think i'd be posting here? All rights belong to ASP. (I'm only gonna say this once!)

Okay, this is the first chapter of my new story, it took a while but I finally think it's ready. My FAOF readers please don't worry, the next chapter will be up shortly, but I just wanted to see what people thought of this before I continue. Though I should warn you that this will be a bit more mature and Rory may seem a bit OOC at times but I will try to stay true to her character as much as possible.

Crooked smile

The Woes of a Good Girl and A Very Bad Boy

Rory Gilmore was seventeen years old and lived a wonderful, blessed life; with a loving family, in a supportive, close nit community. She and her mother were freakishly linked; sometimes it felt as if she was more like her sister and best friend, but she could be just her mother when she really needed her to be. They had lived in Stars Hollow since Rory was a baby, just the two of them. Rory's father would check in with them every once and a while but she came to understand at a very young age that he would never be a staple in her life. Recently though, her mother had decided to add to the number of people living in the Gilmore house. Twelve months ago, after years of continuous flirting and of being an agonising tease, Lorelai had finally decided to through caution into the wind and began to date Stars Hollow's own surly diner man himself. She couldn't have been happier for her mother; they were perfect for each other; though many of the townsfolk placed bets on how long it would last. Three months ago, however, all bets were off when the two finally tied the knot. Luke was now her step – father. Her family was now complete. On top of that, she and her wonderful, caring boyfriend Dean had just had there one year anniversary, she had great friends, her school routine was down, her grades were great, as was everything else. Yep, everything was great. Great, except for one thing. She was so bored!

She knew it might have sounded ungrateful but there were only so many light and fluffy, like cotton candy days a person can take before they're physically sick. She needed some excitement. Nothing in her life was thrilling; she always played everything so safe, right down to the gut she was seeing, she was safe. It's not that she didn't care about Dean; she wouldn't have stayed with him so long if she didn't, right? At first everything had been great, he was just what she wanted; kind, polite, her mother liked him but now, every time she was with him it felt like there was something missing. She couldn't think why, Dean hadn't really changed, he was slightly more possessive but other than he was exactly the same. Exactly. Maybe that was the problem? Dean may not have changed but her wants and needs certainly had. That's why she'd done something bad –very bad. Well, for her, anyway.

She didn't know what had come over her, but she just couldn't help it. It was a Wednesday afternoon, about four weeks ago, and the bell had just ringed, signalling the start of the lunch break. She was just walking through the hall, when suddenly somebody grabbed her arm and pulled her into the girls' bathroom. Tristan.

"What the hell do you think your doing?" she'd asked, appalled. He didn't answer; he just pushed her up against the door and forced his lips onto hers. She wanted to push him away and slap him across the face. She had a boyfriend, of which he was fully aware! A million thoughts were running around her head. She couldn't do this! She shouldn't do this! But as soon as he started nibbling on her bottom lip she lost control. Instead of pushing him away, she wrapped her arms around his neck and pulled him closer. All of a sudden they were heavily making out in the middle of the girls bathroom. After a while, he moved her across the room and propped her up next to the sink. They continued there for a time, and then his hand began to move up her leg. She didn't mind it at first; at least she knew for sure he was a bit more adventurous than Dean. But when he started to move up her skirt she pulled away, and then ran from the room without looking back.

She still couldn't believe what had happened. However, that was not all. A few days later it happened again. And then again and that's how it continued for a few weeks until the moron got himself shipped off to military school. She wasn't heartbroken over this as they both knew it wasn't the romance of the century, or even a romance at all but she was sure going to miss the distraction he gave her and the occasional thrill. Oh, God, when had she become this girl? The girl toying around with boys feelings, one of those girls she despised. It wasn't that she didn't care for Dean, she did, truly but lately it was more like caring for a friend than a boyfriend. She knew she should break up with him but everyday he told her he loved her and she just couldn't bring herself to crush him. That's why Tristan had been so convenient. He was no where near Stars Hollow, and they only got together during school hours so Dean had no reason to suspect anything. However, she had suspected that Tristan may have hoped it would blossom into something more but she always tried to make it clear that wasn't what she was looking for. She had that. She'd had enough of that.

She knew it was trivial but she wanted the toe curling romance she read about in books and saw in movies. Some people would say it doesn't exist, that it's all make believe, but she refused to believe it. She wouldn't rest until she found that passion in her life. But all that would have to wait. It was now eight on a Saturday morning and she could smell the pancakes Luke was making in the kitchen and decided it was time for breakfast. She opened her door and walked into to the kitchen, and saw Luke standing next to the stove and Lorelai reading the paper at the table. Lorelai looked up and smiled at her.

"Morning, sweets."

"Morning Mom, morning Luke." She smiled and then sat down next to her mother.

"Hey, Rory. Do you want some pancakes?"

"You know it!" she sat down at the kitchen table, after pouring herself a cup of coffee. "Umm, this is a good cup of coffee! It's so much more convenient having our favourite diner owner living with us, now!"

"Isn't it!" grinned her mother.

"It's nice to know I'm appreciated!" said Luke as he handed Rory her pancakes.

"Thanks, Luke. Hey, shouldn't you be at the diner right now?"

"Err, no, I got Caesar to open up today."

"Oh, why, are you two up to something?"

"No, Jess is coming today." Oh, right, Jess; Luke's wayward nephew. She never met him before. Or his mother. She got the impression that she and Luke weren't very close, especially when she hadn't turned up at the wedding. But she still had the nerve to dump her kid on him when things got a little tough for her. She phoned to ask him about it about a month ago. Luke and Lorelai had spent two weeks discussing Jess moving in with them and in the end they decided that they would try and help him onto the right path. There was plenty of space since they had built the extension onto the house just before Luke moved in and Luke was pretty much convinced that if Jess was left any longer in his mother's care he end up in prison or dead. However, they hadn't really asked Rory what she thought about it, she wouldn't have objected, but she couldn't help but remember a time when her mother checked with her about everything.

"What time does he get here?"

"Around ten. Do you two want to come and meet him at the bus stop with me, or do you just want to wait until later."

"Err, later. I promised Lane I'd meet up with her today." said Rory, but as Lorelai began to speak her phone went off, and she began rushing around the house trying to find her shoes. "Oh, there was some crisis at the inn, I'm gonna have to leave early. Sorry, I can't come with you babe."

"Oh, okay." And with that, and a kiss on the lips for Luke and one on the cheek for Rory she was the door. Leaving them alone.

Rory and Luke chatted for a little while longer as she finished her breakfast and then she ran to meet Lane. She really needed someone to vent to. Lane was the only person she had told about Tristan, she wasn't really approving but Rory knew that Lane would always be understanding. She met her at the gazebo, away from the prying ears of Mrs Kim.

"Do you think that I should tell Dean about Tristan?" Her friend looked at her incredulously.

"Are you INSANE! Come on Rory, you said that this "fling," for lack of a better word, was just that – "a fling." As in nothing serious! And you said Tristan was gone now, so what's the point of breaking Dean's heart? He's crazy about you Rory! Maybe if you tell him that you need some space he'll ease off and things will be good again!" Rory sighed.

"I just feel like there's something missing."

"Well, if things don't get better then you should break up with him so that you both have a chance of being happy with someone else." Lane gave her a sympathetic look and Rory nodded.

"You're right. You're absolutely right." Lane looked at her watch and sighed.

"I've gotta go, Mamma said I had to help her do inventory today. But hey do you wanna hang out tonight?"

"Oh, sorry I can't. Luke's nephew's coming to town today and we're all going to have dinner together to get him settled."

"Is it weird that you're going to have another guy living in your house? One that you've never met before, I might add."

"Ugh, I know. On top of everything else I have to deal with now I have put up yet another member of the male species. He's probably going to be some pimply stoner that probably doesn't know the difference between Hemmingway and a Hamburger!"

"Hemmingway is a dead writer, right?" asked Lane, smirking.

"FUNNY!" Lane laughed.

"I'll see you later." Rory waved goodbye to her friend and then got up to go for a walk around town, trying to figure out what she was going to say to Dean.

Luke meanwhile was sat at the bus stop waiting for his nephew to arrive. He still couldn't believe Lorelai had agreed to let Jess to come and live with them. She'd never met him and he hadn't seen him for ages. He was just getting used to being a married with one teenager to look out for, how would he cope with living with another one? He shook his head; it was too late to back out now. He and Lorelai had pent weeks talking everything through, and he knew that this would be best for him. Liz was finally trying to get her life together and he thought that was great, but she had already screwed up her son's life so far and he thought it was best for Jess to have some stability while Liz got her act together. He knew he probably should have got involved sooner but he and Liz weren't really on speaking terms for a good few years. But now he could try and help. Hopefully, with Loralai's help he could stop him from falling off the face of the earth. Or worse, like his father, wherever the hell he was. Luke was pulled out of is train of thought, as the bus pulled up in front of him. Several people got off, until finally he saw a mass of unruly hair descend the bus steps.

"Jess." He nodded.

"Luke." He scowled. Luke nodded again and then led him the way to their house. Jess followed, hauling his duffle bag over his shoulder as he walked. On the way, Jess couldn't believe his eyes. It was as though Willy Wonka had thrown up on the place. There were mothers and daughters dressed the same, and everywhere he looked someone was skipping. And on one street corner he could have sworn that there were teenagers sitting at a lemonade stand. What was wrong with these people? His mother had grown up here? Huh, maybe her smoking pot for the better part of her life wasn't the only reason she was such a basket case? When they got to the house he stopped outside for a moment to take it in, it looked relatively normal but looks can be deceiving.

"Okay," voiced Luke, when they finally got inside, "this is it. Your room is upstairs and then down the hall from mine and Lorelai's, just on the right. There's a bathroom upstairs next to your room and there's one next to the kitchen, across from Rory's room. Both her and Lorelai will be home later." Jess just nodded, dumbly. "So, is that all your stuff?" He asked, signalling to Jess' duffel bag.

"Yep."

"There's not much there."

"Yeah, well, Lizzie's sending the rest later."

"Right, right. So, do you want something to eat? I could see what we have in the fridge or you could come to the diner with me?"

"Diner?"

"Yeah, that's what I do. I own a diner; it was your Grandpa's old store-"

"Huh." Jess nodded, feigning interest.

"So, do want something to eat?" Jess shook his head.

"No, thanks. I think I'll just stay here and take a shower. Being on a bus for any extended period of time can make you itch."

"Sure. Oh, but now that I think about it, the shower upstairs isn't really working properly, there's no pressure coming through, so you'll have to use the one down here. The towels are in the closet next to mine and Lorelai's room, on the left."

"Okay, thanks." They stood in an awkward silence for a moment before Luke decided it was okay for him to leave.

"Well, I better get going to work. Rory should be back soon and Lorelai usually gets home at about six so we'll all have dinner together tonight and you can get to know them. So, I'll see you tonight."

"See, you tonight." And with that Luke turned to the door and left, leaving Jess alone in the house. He sighed and looked around the room. Well, it could be worse. He picked up his duffel bag and went upstairs to find his room. He went to the end of the corridor on the right and open the door, to what he assumed was his room. It was a decent size and rather plainly decorated with pale blue walls and several empty white shelves and cabinets. In the centre of the room there was a double bed with dark, stripy blue sheets that matched the curtains, which he assumed had been picked out especially for his arrival. He walked over to the bed and dumped his duffel bag on the bed, along with his jacket. He then moved over to the window and looked out at the town of Stars Hollow. The sun was shining brightly, birds were singing, children were laughing, running and skipping, some were even wearing the same clothes as their parents – it made him SICK! What was Liz thinking sending him here! He'd probably try to kill himself by the end of the week! She must have known that, she grew up here. Oh, boy, that explained a lot! He shook his head and headed for the shower; he was beginning to repeat himself in his own mind thanks to this place. He might feel better after a wash but he doubted it.

--

Rory walked back into the house, very depressed. She'd been walking around the town for over an hour, trying to figure out what to say to Dean. She really didn't want to hurt him but she didn't want to be with him anymore. She began to walk to her room and realised as her mom and Luke wouldn't be home yet, and as their shower was on the blink, now would be a good time to take one. She opened her bedroom door and began to peel off her clothes. As soon as she had unclasped her bra and thrown it onto her bed, the bathroom door behind her opened and she whipped around in shock. Stood there was perhaps the most gorgeous boy she had ever seen, dripping wet and completely naked apart from the stripy blue towel around his waste. He had sexy dark hair and olive skin, but she couldn't help but stare at his well toned chest. It wasn't until her eyes made it back up to his face that she realised he was also staring at her very naked chest!

"OH MY GOD!" she screamed, grabbing her bathrobe off the door and covering herself, as he stumbled back a little. "WHO THE HELL ARE YOU! AND WHAT ARE YOU DOING IN MY SHOWER!"

--

Jess had been in the shower for about twenty minutes when he decided that he had finally gotten rid of the grungy bus smell, and stepped out grabbing his towel from the railing. He wrapped it around his waste and unlocked the door. No sooner had he opened it, when he greeted by someone else's bare flesh. At first he saw nothing but her back but barely a second later, he was faced with a pair of creamy - white breasts. He seemed to be staring at them for ages before-

"OH MY GOD!" she screamed, as he stumbled back, holding his towel on his waist. "WHO THE HELL ARE YOU! AND WHAT ARE YOU DOING IN MY SHOWER!"

"I'm Jess, Luke's nephew. I got here about thirty minutes ago. Luke told me to use this shower, the one upstairs is broken." She sighed and closed her eyes nodding; oh yeah, now she remembered. She was about to apologise, when she realised they were both still half naked, and then quickly shut her bedroom door. DEAR LORD, 'HE' was going to be staying with them! She wasn't sure if it was better or worse, but one thing was for sure: she had enough boy troubles.

--

After she had slammed her bedroom door shut, he stood there for another few moments stunned. WOW, he never expected a meeting like that! He then realised he was dripping on the floor and was about to head upstairs but then decided it would be best if he took another shower. A cold shower. But on the bright side, Stars Hollow might not be that bad after all.

--

A/N : HHMM, not quite the same innocent meeting it was originally but I hope you enjoyed it just the same. Please tell me what you think. Or if you hav any questions please PM me.