Summary - Rory went with Jess at the end of her first year at Yale, but instead of New York, they went to California. Things didn't work out, but things had changed too much to go home. What happens when she meets the friend of her neighbour? He's got close ties to her old life but he has some secrets of his own.

AN: Well, I do need another story, right? Anyway, this has been sloshing around in my head, originally what I had planned was twofold, one multi chapter story, and a one-shot. I have combined them. I envision this being about 20 chapters long (remember when I said that about Later ... joke was very much on me). Anyway, here we go, hoping for Later update tomorrow or late tonight and another of this by the end of the weekend

Disclaimer: I own nothing

Chapter One

She was exhausted. Although, she supposed she was always exhausted these days. Rory Gilmore had been working for close to eighteen hours at this point and she was exhausted. Two jobs. She worked two jobs to pay off her student debt, the debt she had because she refused to accept a bailout from her grandparents or her father for what had been her monumentally poor decision of leaving Yale after her first year and moving to California. California…it had been so much fun at first. She had transferred to Berkeley and taken out astronomical loans, she worked through college and split the cost of a tiny studio apartment with Jess Mariano. Jess Mariano was the man who had made Rory think that together they could take on the world. They were happy once, when everything was shiny and new, but eventually the shine wore off and Rory found herself juggling school and work, struggling to make ends meet while Jess was always sure he was on the verge of his next big break with his writing. To be fair he had published two books during their time together, neither had been hugely successful, but Rory had been proud of him. When things were good, they were good, but that was always how things were with Rory and Jess.

By the time Rory was finishing her degree, things between Rory and Jess were reaching their natural end. And so, instead of letting things end, they had tried, of course, they fought, they made up…by the time she finished getting her teaching certificate, the animosity had reached a point of no return. They weren't meant to be together anymore, and much to her own surprise, Rory found herself packing her bags one day while he was gone and moving to San Francisco to live with her former roommate and friend, Paris Gellar. Paris of course had graduated from Yale and then come to UCSF for her masters and then med school. Rory had secured a job teaching and then found a second job as a bartender in an effort to keep on top of her bills. There was of course another option. The option was to mend fences. Mend fences with her mother and her grandparents after years of uncomfortable turmoil. Of course she still spoke to her mother, but it wasn't like before, and she as acutely aware of the disappointment that Richard and Emily Gilmore felt after she left Yale. She wasn't sure though, she wasn't sure how to go back to how things used to be, and maybe she wasn't even sure if she wanted things to go back to the way they were. She couldn't think about it though, her eyes closed as she rode the elevator to their fourth floor condo, she was twenty nine and things certainly weren't going as they were supposed to. It was after two in the morning of course, she had closed at the bar and earned her fair share of tips for the evening, enough to make her feel like getting hit on by sleezey old men was worth it. For the most part she enjoyed her job at the bar. She talked to interesting people, she had fun with it…but some nights involved guys who were old enough to be her grandfather making inappropriate jokes that made her cringe. Her coworkers were always there to step in, and she was thankful for that, in the three years she had been working there, she had created a little family of her own. They spent birthdays together, Thanksgiving and Christmas on the years that Rory didn't return to Connecticut. Although the life she was living in San Francisco wasn't exactly the life she had planned, she enjoyed it.

"You close again?" a voice interrupted Rory's thoughts and she smiled at the brown haired man who evidently had gotten off the other elevator just a moment before her.

"I did. Did you?" Rory asked with a smile.

"Different reasons I suppose."

"Yes, you were drinking, I was working. How was your week?" Rory asked as they walked down the hall towards their respective apartments.

"Long, boring. Lots of people getting divorces."

"Keeps you busy Colin," Rory tried to tell him optimistically but she wasn't sure it didn't come out bitterly. She was after all exhausted.

Colin McCrae smiled at his neighbour, he had moved in six months earlier and they saw each other in the halls and a few times he had gone for drinks where she worked. They were friendly, not friends, but he worried about her. He knew she was always leaving for work before him and coming home at the same time as he came home from a night of partying. "You work tomorrow?" he asked her as they stopped at her apartment.

Rory shook her head, "no, day off…"

"How many weeks has it been since a day off?"

"Colin, I need the money."

"Answer the question Gilmore."

"Five."

"I'm having a party tomorrow," he told her, "my friend Finn, you remember him? Australian? Obnoxious? Tall?"

"Who could forget Finn?" Rory was pulling her keys out, she had met Finn a few times in the hallway with Colin, and at the bar where she worked a couple of times as well. Smooth talker, generous tipper and Rory had come to believe he was more of a loveable oaf than anything else.

"It's his birthday, we're having a party to celebrate another year of Finn. You should come, bring Paris. This is in no way me asking you out," Colin clarified, he realized how she might be perceiving his invitation, "just a friend who thinks a friend could use a night to relax."

"Text me the details," Rory told him, it was the kind of invitation she would normally blow off, "we'll see."

"Come on," Colin waited another moment while Rory opened the door and stepped inside. "Goodnight Ror."

"Night Colin," Rory smiled. She knew what he was doing, whenever they got home at the same time, he made sure to check that she was safe in her apartment before he left. She wasn't sure why, but she was pretty sure that he was trying to be chivalrous. "Paris?" Rory noticed that the lights were on and the sound of the TV was coming from the living room, "you up?" she asked as she saw her shadow on the couch.

"I'm just watching the end of this documentary," Paris finally responded as the show cut to a commercial. "How was work?"

"Long, tiring, boring," Rory placed her bags on the counter, "I'm going to bed. Colin invited us to a party at his place tomorrow."

"I can't go to a party, I have to be at the hospital tomorrow night."

"Alright, so that is a no from you."

"Are you going to go?" Paris asked.

Rory shrugged her shoulders, "maybe. I don't work. My alternative is what…watching documentaries about world war two or…."

"Don't knock these, many medical, technical and scientific advancements came out of the need for the Allies to respond to the war."

"I'm not knocking it Paris, I'm just saying it isn't how I want to spend a Saturday night when I've been invited to a party."

"So what, are you going to date him?"

Rory shook her head and made a face, "we're friendly. I wouldn't even call us friends. Not that it would be a bad thing to make a few more friends here, after all it's been three years, but he specifically clarified that this is not a date, and I do not want to date Colin. It's just a party."

"Sure," Paris shrugged her shoulders.

"Goodnight Paris," Rory exhaled loudly and grabbed her bag to walk to her bedroom. Her bedroom was, of course, smaller than it's counterpart. Which made sense given that Paris had lived here first. Her longtime boyfriend, Doyle McMaster had lived with her at first, but he had moved for a work opportunity and they were doing the long distance thing, so Rory moving in was the perfect way for them to offset some of those costs. She hung her bag in her closet and quickly pulled out a pair of pyjamas that her mother had given her for Christmas the year before. Matching pyjamas…Rory, Luke, Lorelai and Luke's daughter April had all looked ridiculous in the flannel pyjamas from Old Navy, but Rory appreciated the effort her mother was making. They still had a long way to go, but things were slowly improving, after all it had almost been ten years now. Nearly five years of Jess, and then these last three years of being in San Francisco, Rory could hardly believe how long it had been since the life she had known. Rory climbed into bed and made sure her phone was charging beside her. Before her head had hit the pillow, she was fast asleep.

As she did most days when she closed, Rory slept in. It was after noon when she woke up which anyone who knew Rory before she moved to California would tell you was uncharacteristic. When she was living with Jess it was because they would be out and about, at bars or clubs, sleeping off a hangover until the middle of the afternoon some weekends, now though it was because of work. Rory would stay up late during the week staying on top of her marking and lesson plans, and most weekends Thursday, Friday and Saturday she would work at the bar. Friday and Saturday were typically her nights to close, although somehow she had managed some reprieve this particular weekend. That reprieve ended quickly though. A call from her boss to ask her to come into work, they were short a person and a quick reminder to Rory that the tips would be great on this particular day and she would be working with a team of her friends, what sealed the deal though was her boss promising to cover her Uber back to her apartment. She agreed quickly, she was hoping that she might be able to fly back home to Connecticut to celebrate her mothers birthday in a couple of months, and a few hundred bucks in tips would go a long way towards that. Rory texted Colin apologetically, explaining that she had intended to come but she had been asked to work, he responded that he understood but that if the party was still going on when she got home, she should come in for a drink at the very least. They both knew she wouldn't. They knew that by the time Rory got home from work she would have no interest in doing anything except climbing back into bed and enjoying her only day off. Tonight however as she came down her hallway, she noticed first off that there was no noise bouncing down the hall except for the sound of a knock on a doorway. No music pulsing from Colin's unit, but instead Rory felt her body tense as she saw that the knocking was coming from a man in front of her door. Doyle? No, she told herself as she got closer. Doyle was shorter and stockier, Doyle had much darker hair. Her fear dissipated slightly as she got closer and she could hear what the man was saying as he leaned against the door.

"Col, come on…. open up."

He was looking for Colin's place, which led her to believe that he was very drunk, and also very lucky that Paris wasn't home to kill him. Rory waited for a moment to see if the man noticed her but he didn't and so she cleared her throat and gripped the pepper spray that she kept in her purse. "Uh…hi….can I help you?" She recognized the man, having seen him with Colin before, but she had never been introduced to him.

The body turned towards her and gave her a charming smile that confirmed that he was in fact drunk. "You," he looked her up and down, "are not Colin."

"Give the man a star," Rory laughed, "Colin lives there," she pointed to the apartment across the hall.

"Ahhh, yes, sorry about that…you don't look….scary?" the man squinted to look at her once more.

"Scary?"

"Neighbour…Colin….scary."

Rory laughed, "that is Paris. So what…locked out?"

The man dug his hands in his pockets and pulled them out empty. "Phone and wallet, inside. Colin…not inside…"

"Well he's certainly not inside here," Rory nodded to her door. She released the grip she had on the pepper spray in her purse and pulled out her cellphone instead, "I'll call Colin," she told him as she dialled the number on speaker. After a few rings it went to voicemail and Rory could only assume what Colin was doing or who he was doing it with if he wasn't home.

"I'll just sleep here," the man told her.

Rory groaned, she was too tired for this. "I can order you an Uber?"

"Can't go home," his words were slurred as he slumped down the wall onto the floor and offered no further explanation as to why he couldn't return home.

"Get up," Rory told him as she unlocked her door.

"Huh?"

"Get up," she repeated, her annoyance showing as the drunk man that she had seen before with Colin slowly stood up. "You can crash here. I have to assume my straight laced neighbour who makes sure I am safely in the door before he walks away isn't friends with any murderers, so please don't prove me wrong."

"Promise," he followed her through the doorway. "I…Logan."

"Rory," Rory watched as he kicked off his shoes slowly and she walked further in. "Look, my roommate, the scary one, she will freak if she finds you on the couch. So you sleep in here," Rory was shoving him through the doorway to her bedroom, "I will sleep on the couch."

"Nah," he shook his head, "you can't on couch," he was aware that he had missed some words there, "you can't sleep on the couch," he spoke slower but while he spoke she grabbed pyjamas from her drawer and then left for a moment.

Rory returned with a bottle of water and two Aspirin, "drink," she told him, "swallow," she added. "Bathroom is across the hall. We'll get you over to Colin in the morning."

"Thank you."