This story is set when Rory is 25. Jess never came to visit her in season 6 and she slowly went down hill more and more, never returning to Yale. Lorelai and her are estranged, she's engaged to Logan, she doesn't speak to her grandparents either, but stays with her father often.
I don't really know where I'm going with this, I have some good ideas though.
Disclaimer: Good lord I don't own anything at all!!
Chapter 1
The music blared and Rory could hardly stand it. Logan grinned at her through the crowd of people, she looked away, not even acknowledging him. She looked over at Finn, catching his eye, he grinned and got up, she knew where he was going and a moment later she followed him.
Finn took her hand, running his finger across the ring on her fourth finger.
"Something about touching this ring makes me feel 10 times naughtier then I already do." He chuckled, running his other hand through her hair.
"That's because the ring is what makes it so exciting. So evil!" She laughed, leaning forward and kissing him passionately.
"Naughty, naughty girl!" Finn hissed, pulling away from their kiss.
"I wish we could get out of here." Rory shouted to him over the roar of the dance music.
"I think that would make it a little obvious." Finn laughed, pulling her close so their bodies were warm against each other.
"I guess… and if everyone knew…it would just be boring and I'd move on anyway." Rory said with a shrug. She was entirely serious.
Since school, Rory was constantly searching to fill the space it had left in her life. Drinking, drugs, sex were just a few of the things she used to escape the fact that she had disappointed herself, and everyone around her.
"This place is boring now, I'm going to take Logan and I'm gonna go." Rory told Finn, who shrugged.
"I'm gonna stick around, try and fool some dazzling creature into coming home with me." Finn told her.
"Good luck with that." Rory called, and then set off through the crowd of the club to where Logan was. "Let's go." She called to him, he nodded and followed her out into the cold winters air. "So not dressed for summer." She said, pulling him close to her and wrapping his arm around her shoulders.
"You didn't seem to be having fun tonight." Logan told her, she nodded.
"It's all the same old shit, I need something new." Rory replied, watching her breath turn to smoke as she spoke.
"Maybe you could try going back to school." Logan said, he constantly brought this up to Rory and it infuriated her.
"It's been over 4 years since I left! I'm not going back Logan." She snapped at him, "I can't go back." She added bitterly, a hint of sadness in her voice.
Logan kissed her on the forehead, and they walked down the street in silence. Rory looked around the quiet streets of New York, her home for what seemed like forever, she could hardly comprehend living in a small town now, she hadn't been back to Stars Hollow in three years, and it had only been to see Lane before that. These days she simply made Lane come and meet her in Hartford.
"You know I worry about you Ace." Logan told her for about the millionth time.
"I worry about me too." Rory replied, not in the mood to fire up and fight with him. She felt Logan's sigh and she felt a pang of guilt for the things she did behind his back. These pangs were rare, and were getting further and further apart as time went on. Rory could feel everything she used to know about herself slipping away and she didn't care.
They reached their building, it was a huge grand looking estate, the doorman smiled at them, tipping his hat gently.
"I think I'm going to have a cigarette before I head upstairs." Rory told Logan.
"I don't want you to stand down here on your own, I'll keep you company." Logan told her.
"No, you know I like to be alone when I smoke, it's my thinking time." Rory told him with a small smile.
"It's cold out, and it's the middle of the night…just let me stay…" Logan said.
"Norm will keep me company, just go upstairs…get naked and I'll be there in no time." Rory said cheekily, slapping him on the butt lightly.
"All right Ace. But, don't talk to strangers." Logan warned with a chuckle in his voice, then he went inside, Rory watched as he got into the elevator and disappeared from view.
"Nice night to be standing in the blistering cold, ain't it Norm?" Rory said with a grin to the doorman.
"For the millionth time Mrs Huntzberger, my name is Pauly, not Norm." Pauly told her with a roll of his eyes.
"And I'm not Mrs Huntzberger, but you insist on calling me that, so I'm gonna keep on calling you Norm…Norm." Rory told him, lighting up a cigarette and inhaling deeply, closing her eyes as she took a seat on the stone steps.
"That stuff will kill ya." Pauly told her, she sighed softly.
"You're a real brains trust Norm, what say you and I run off together?" Rory told him giving him a withering stare. He was quiet after that.
It was freezing but Rory didn't mind, her hair was very long now, and dyed burgundy, it fell down her back in thick waves. She was wearing a blue dress with spaghetti straps, it came to just below her knees, so needless to say she was shivering so much it almost felt like she was having a fit.
She could see a group of people walking towards her, hooting and jumping around, the streets of New York never slept.
It was times like this, when Rory would dare to think about her mother, and what she was doing, and if she was alright. Rory would never admit that she thought about her mother to anyone, she never bothered to ask Lane about her, in fact she purposely avoided it, and these days Lane didn't even bother to try.
"I'm going home for the night in a moment Miss, perhaps you should come inside." Pauly told Rory, who blatantly ignored him.
Rory was thinking about the last time she had seen her mother, last Christmas.
"You're wasting away." Lorelai had said to Rory, feeling sick at how thin her daughter had gotten.
"Eating's not really up there on my list of priorities. A lot more coffee these days though, you must be proud of that." Rory told her mother.
"Not even in the slightest…" Lorelai snapped back, they were silent for a moment, "I see you're engaged…Logan I presume."
"Didn't see the point in saying no when he asked." Rory said with a shrug, looking down at the incredibly expensive engagement ring. "We'll probably just end up being engaged for years."
"I'm glad you're taking it so seriously." Lorelai replied.
"You look good mom." Rory said softly, she heard her mother let out a little sob, so she rose up from the grandparents couch and went to find Logan so they could leave.
"Night Miss Gilmore." Pauly said, taking his doorman hat off and heading off down the street.
"Night Pauly." Rory said back with a small grin.
She looked at her cigarette, the ash was extremely long, she had been completely lost in thought, she threw the cigarette away and lit another, standing up and stretching.
The group of people was only about 10 metres away now, 3 very beautiful girls led the way, then a few boys, pushing and shoving each other like they were still 10 years old, then a boy and a girl brought up the rear.
"Evening Ma'am!" The boys hooted as they passed by Rory, they were around her age, she grinned back.
"Rory?"
She looked around at the boy who had his arm around the girl.
It was Jess.
She looked at him.
He looked at her.
There was silence.
Rory threw up all over her shoes.
