A/N: So I've been thinking about this idea for quite some time, and finally got around to putting it on paper (figuratively speaking). It came out much longer than I thought it would, haha. I do have more planned for this, and am actually working through the first part of the second chapter. But after that, I only have vague ideas so please be patient with me because I'm a NOTORIOUSLY SLOW writer when it comes to multichapter stories and such. Also, I hope this okay in terms of being in-character; I've never written anything Gilmore before, so it might take me a bit to get a hang of it.

I'd love to dedicate this to my amazing friend Veronica (tumblr: tylerhecklins) who adores Rory and Logan and helps me run our Gilmore Girls blog, gilmorelovers. I love you dear! I hope you like this! 3

June 16th, 2004

Rory leaned against the small counter in their kitchenette while clutching a cup of coffee tightly in her hands. Looking around the small, sparsely decorated one room apartment, she released a tired sigh. It had been a month. They had been living together for around a month now, and there were no signs of it anywhere. Not in pictures on the walls, towel sets in the bathroom, or even a shared book collection. In fact, they barely had shared lives. This wasn't what she had wanted, what she had expected.

Look, we'll go to New York. We'll work, we'll live together, and we'll be together. It's what I want. It's what you want, too.I want to be with you, but not here. Not this place, not Stars Hollow. We have to start new.

No. She should have said no, she finally admits to herself. But she had hesitated, and eventually let herself be swayed. He had caught her off guard. Jess had just shown up on her doorstep unexpectedly with wild plans of grandeur. He said they could run a way to New York together. Jess had always been the spontaneous type, that hadn't been a surprise to her. Honestly, it was actually part of why Rory loved him. What had made her stop to reconsider was how he told her he was finally ready. He said he knew they were meant to be together. She remembered wanting to believe him so badly. She wanted to give him a chance.

So she did. She set her now empty coffee mug in the sink and walked over to the living room where her half-empty college boxes still resided. She didn't even need to stop home first; all her stuff was packed and ready, he had said. But why had she never fully unpacked? Why was she still living out of boxes like a guest in what was meant to be their home? She gingerly sat down on the worn, faded leather sofa. Pushing a piece of her almost shoulder length hair behind her ear, she just kept wondering what went wrong. Why had they become like this?

She stilled her anxious fidgeting and listened to the rapid clacking of the computer keys in the next room. Jess had begun working on this book, this great novel, almost the day they arrived in the city. She had encouraged him at first. She was so proud that he had the ambition and drive to make his imagination come to life on paper. He was finally putting of all of the intelligence and potential she knew he had into something worthwhile. But things had quickly begun to spiral out of hand. It wasn't that Jess was simply writing a book anymore. It was almost as if he was being consumed by it. It was all he ever did, all he ever even thought about.

Rory released a deep sigh and leaned back against the cushions as her thoughts drifted idly to her mother. They hadn't spoken since she left for New York. Rory had called when they were en route to the city, excited to share the news that her and Jess were finally going to start over together. She was well aware that her mom wouldn't be entirely thrilled she was running off to live with her boyfriend, but she hoped Lorelai would try to be supportive. Her stomach turned thinking of the bitter argument that had taken place over that phone call. The angry and hurtful words spoken would still echo in her mind from time to time.

She missed her mother so much. Actually, she had missed a lot of things since she left. She wasn't there for the opening night of the Dragonfly Inn, Lorelai and Sookie's pride and joy for the past year now. Rory didn't know that Lorelai and Luke had finally gotten together that night after years of dancing around each other. And she certainly didn't know about Dean and Lindsey's huge separation that occurred only weeks after she had left.

Rory pursed her lips together in in self-recrimination. She knew that her and Dean had gotten much closer in the past couple months and she just knew that if Jess hadn't come back into her life, then something would have happened between them. And she never would have been able to forgive herself. Because he's married. Or was married. Regardless.

Even if she hadn't physically cheated with Dean, she would still feel culpable of any part she could have caused in the crumble of his marriage. Rory had discussed this as thoroughly as she could with Lane, one of her few consistent contacts from home, but neither had come up with anything either alleviating or recriminating.

Rory stood abruptly in some sort of attempt to shake off her depressing thoughts. She needed to get out of the apartment and do something. She had miraculously been able to find a job as a fact checker for the New York Post a few weeks ago and today was one of the first days off she'd gotten. For God's sake, why was she still mulling around the living room?

Walking down the narrow hallway leading to the bedroom and bathroom, she stopped in front of the half open doorway where Jess was hunched over his laptop with his eyes drawn to the screen. A half drunken cup of coffee was leaving rings on the Formica, and there were crumpled notes of loose leaf scattered everywhere on the desktop. "…Jess?" she asked slowly, knocking softly on the doorframe.

"Uh…yeah?" he answered without even glancing up from his work.

"Jess, it's really nice out, and I have the day off. Do you want to go out for coffee or something?" she squared her shoulders and asked out right.

Finally glancing up at her briefly, "I really want to finish this chapter today."

"Well, how long is that going to take?" she pursed her lips, momentarily put off.

"I don't know, Rory. I'm just letting the characters take me where they want."

'What does that even mean?' she thought to herself with a scrunch of her face. She released a deep breath and tried to be patient. She knew snapping at him wouldn't benefit either of them in the long run. "Would you mind just putting the characters on hold for a couple hours though?"

"No, Rory, I can't," Jess retorted, finally leaning back in his chair and giving her his full attention. "If I don't get this all out now, I'll lose my inspiration. I thought you of all people would understand."

"I do understand, but I feel like all you've done since we got here is write!" she burst out. She then deflated against the door frame, rubbing her temple tiredly. "I just thought that we'd be spending a lot more time together since, you know, we live together now."

"Hey, I'm sorry. I am, Rory," Jess softened, standing up to come in front of her. "But I've always wanted to do this. I've wanted this before I even knew I did, and I can't just forget about it now that I've finally just gotten started."

"No, I'm sorry, Jess," she furrowed her brow while cupping his jaw gently with her palm. "You're right. I should be more supportive of you. I know that, and I know how much you want this."

"Thank you," Jess smiled, placing his hands on her hips warmly while rubbing circles gently on her bare skin where her tank top had ridden up. "You don't know how much that means to me."

"It's just that I miss you. And I miss spending time with you. Which is crazy, right? I mean, it should be. Because we live together; we moved here to start over on our relationship," her voice broke as she couldn't help her insecurities come through.

"Rory! I do want to start over with you! When I said that, I meant it," he exclaimed emphatically. He paused, grasping her closer to him. "I just need to finish this! I need to do it for me. Please. Just give it a few months or so."

"Months? Jess! You know I go back to school in August," she broke free from his embrace in exasperation, "I don't have months to wait for you!"

"What's that supposed to mean? Was this just a temporary thing for you, huh?" Jess whirled on her in sudden fury. "Some fun summer fling until school in the fall?"

"Of course not!" she snapped offensively. How could he even think that? After everything she'd done to be here with him? "You know I have no intention of breaking up with you when I go back to Yale! I was trying to say that it won't be the same. We won't have limitless time together. I'll have classes, and you'll be here in New York. We'll only have weekends, phone calls, text messages. It's going to be harder."

"I asked you to transfer to NYU, but you said 'no,' and I respected that," he told her coolly. "Because I know it's your dream."

"Yeah, it is my dream," Rory reiterated warily.

"Then if I can so easily support your aspirations, even when they could cause distance between us, why are you having such trouble doing the same for me?" Jess tilted his head in emphasis.

"…what?" Rory's face dropped dumbly. "Do you honestly think that? Do you really think that I don't support you after everything we've been through?"

"Rory, wait-" Jess started.

"I mean, I moved to New York for you! For us!" she exclaimed wildly, completely ignoring his softened expression. Rory began gesturing broadly, gearing up for a classic Gilmore rant. "I left Stars Hollow, and my mom, to be with you! And now we're not speaking! I never wanted to be one of those girls that turned their back on their family for a guy, protected him from them. But here I am! God, this is even worse than in high school! At least then I didn't have to defend you to everyone. Just my grandmother, and my mom. But geez, Jess! I offered to tutor you! And I-"

"Rory!" Jess shouted sharply, grasping her arm to keep her in place. His voice leveled as he held her gaze. "I'm sorry. You're right. I shouldn't have said that, I know. You've been more than supportive. You're probably the only person that has always been there for me."

Letting out a deep sigh, her shoulders slumped. She let her fingers reach up and grasp the sleeve of his shirt to keep her composure. "I know you're sorry, Jess. I just…I don't know. I can't be here right now."

"What? What are you saying?" his brows furrowed in confusion.

"I just need some air," Rory mumbled, abruptly pulling away from him and running out the door and her newfound realizations.

Rory bounced nervously on the balls of her feet. She must be insane to even consider this. Looking up and down the busy New York sidewalk, she resumed pacing in a huff. Normally she would be going to a quiet, little coffee shop to get lost in a favorite, old novel of hers; probably Pride and Prejudice. It's what she always did when she was frustrated. But Rory had no desire to be lost inside her mind today. She wanted to run as far away from her thoughts as possible.

Stopping suddenly, she looked above her at the faded emerald sign hanging over the entryway. Before she could second guess herself more, she pushed open the door and made her way into the pub. It was charming in any way that a bar could be. The green accents and cushioned booths helped accentuate the Irish theme while the wood paneling and low hanging lights provided a relaxed, comfortable atmosphere. The layout wasn't very wide, but it went surprisingly far back and broke apart into different hallways and separate rooms. Rory's journalistic nature wouldn't cease, and, as she slowly made her way to the bar area, she continued to observe all the little details of her new surroundings.

Rory bit her lip as she apprehensively hoisted herself onto the high stool and swiveled herself toward the bar. The bartender, a tall and scruffier looking version of Topher Grace, she mused, paused in front of her. Casually drying highball glasses with a blue dish towel, he slowed his movements to catch her eye. "So what'll it be?"

"Um, just a coffee for me I think," she bit her lip.

"I don't think so," scruffy Topher Grace replied dryly.

"Excuse me?" Rory's brows furrowed in confusion and mild irritation.

"Most people don't come to a bar in the middle of the afternoon just for coffee," he quirked his mouth into a wry grin, "and judging by the way you're wringing holes in your shirt, I think you definitely have stress to drink away."

"Fine," Rory deflated, immediately pulling her hands away from herself, "put a little Irish in that coffee."

"Now that's more like it," he nodded approvingly, turning to prepare her drink. And just as he had passed it down the bar to her, she was shaken out of her intense thoughts of Jess by the harsh slamming of the bar door and a man's voice barking into his blackberry.

She turned her head slightly back to the left to see a blond, spiky haired man in a light blue dress shirt and tie coming toward the bar and sitting next to her. His irate expression gave away enough of the nature of his phone call for her to turn back to her drink out of polite etiquette.

"Yes, I took the rest of the day off!" he snapped back through the phone, balancing it on his shoulder as he rolled up his shirt sleeves and loosened his tie. "Because I don't have to be at that meeting! That's only for board members and the executives!"

Gesturing to the Topher Grace bartender, he covered the phone and quietly asked for a scotch neat. "Yes, I realize I have to get experience. I know that. You don't have to continuously remind me how much of a disappointment I am," he growled through the phone.

"The files are on your desk. I'll be there bright and early tomorrow morning," he cut off the other speaker, rolling his eyes. "Always a pleasure, dad."

Rory's head snapped up in surprise. "Your boss is your dad?!" she blurted out.

The blond turned to look at her in frustration as her eyes widened in complete embarrassment. She hadn't meant to say that at all, the words just seemed to come out. Rory just couldn't believe that someone could have such a hostile relationship with their father. She assumed that working together in a professional setting would most likely put tension between them, but still. Didn't he mention continual disappointment? That's pretty rough.

"Yes," he said tiredly, with a ghost of a languid smile. "He is." He turned his body toward her, placing his elbows on the bar in a way that stretched his muscles over his shirt just so… Rory internally shook herself. She was in a relationship. Maybe not a happy one, but…

"I'm sorry, I didn't mean to, uhh… well, that sucks," she stammered, pulling herself back into the present.

"Yeah, it does, doesn't it?" he laughed in a surprisingly resigned tone, "But I'm used to it."

"That doesn't make it much better, now does it?" she returned the smile, although on the inside she felt for this emotionally guarded, devastatingly handsome man. Rory herself had a pretty strained relationship with her father, having him constantly in and out of her life, but never there to stay. Then when he had finally made a commitment to both her and Lorelai, he had gotten his girlfriend pregnant and once again left them in the dust.

The one thing she could say about her father, though, was that he was always proud of her. He had always loved her and thought highly of her. In fact, if either of them was a disappointment, it was him.

"Maybe, unless you consider all of that 'can't miss what you don't have' shit," his voice lilted upwards as his eyes wandered forward around the bar. His face tightened slightly, lost in uncomfortable memories.

"I'm sorry, you probably don't want to talk about all this with a stranger," Rory tilted her head in apology toward him. She hadn't realized the very personal information she had been drawing out of him, a person she'd never even met before. She had to remember that this wasn't a journalistic interview; it was a normal conversation in a bar.

"Well, you're right about that," he suddenly laughed. "Although considering this instance is actually slightly my fault, I'll make an exception."

"What?" Rory scrunched up her nose, "How could any of that be your fault?"

"Well," he drawled, smirking slightly," The only reason I'm interning for my father this summer is because I... might have sunk his yacht."

"You might have?" Rory burst out laughing at the blond's boyish grin. She was starting to get clearer picture of who her drinking partner was minute by minute. "Wouldn't that be something you'd know?"

"Technically speaking, my friend Finn was the one steering. But he's perpetually drunk and needs constant supervision…" he trailed off, before gesturing widely with hands," Regardless, it turned into this huge ordeal, and the Coast Guard was called in. I'm sure you can imagine."

"Yes, I'm sure," she suppressed a smile. Rory was surprised to find his blasé attitude about literally sinking his father's money away didn't bother her as much as it usually would have. She wasn't one to tolerate people's financial carelessness considering everything her and her mother had been through to become as successful as they were now. Perhaps it was because this man beside her was making up for it every day he spent working for his father. Or maybe because the father in question seemed completely deserving of having his boat crashed. Maybe both. Maybe she just liked him. Rory wasn't sure, and it perplexed her.

They sat in companionable silence drinking their respective drinks until he spoke casually, "And what about you?"

"About me what?" Rory raised her eyebrows at him, her glass still perched to her lips.

"What made you want to drown yourself in alcohol in the middle of the afternoon?" he turned back toward her. "Tit for tat, you know."

"This is coffee," she harrumphed, nervously shifting in her chair. He raised his eyebrows at her amusedly, but said nothing.

"Fine," she snipped, tucking her hair behind her ear, "but it's really nothing. I guess it started when I ran away-"

"Oh, running away from home? That's nothing, is it?" he broke out into an incredulous smirk.

"It wasn't like that," her face dropped into a frown. It's not like she left home because she hated it her parents or her town or her school. Quite the opposite. She shouldn't fall into that stereotype, but she supposed that was people's automatic assumption.

"So what was it like?" he asked curiously, but not sharply. He seemed to not be passing judgment, which was a welcome change. He cocked his head, "was it for a boy?"

"How did you know?" she snapped her eyes up to meet his.

"Isn't it always for a boy?" he rolled his warm brown eyes in a joking manner. Rory breathed out a light laugh, and gave his shoulder a little push. Before bringing his scotch back up to his mouth, he voiced, "so what's his story?"

"About a month ago, my ex-boyfriend just showed up on my doorstep and begged me to move to New York with him," she stared straight ahead trying to stay nonchalant and detached, when in reality the entire situation felt ridiculous and completely out of character to her now. While she had nothing to prove to this man, she didn't want to be perceived badly by him.

"So you said yes," he assumed, lifting his shoulders slightly. "I mean, here you are in New York."

"Yeah, here I am," she shrugged, "I was still in love with him. And we always had so much chemistry and connection and… he just got me, you know? Better than anyone else."

"So what's the problem?"

"Things are just different now!" she exclaimed, throwing her hands up and letting them drop down on the bar countertop. "We're not in high school anymore! Jess is always busy working and doesn't seem to care about what I want anymore. I have to think about school in the fall. Plus, my mom won't even talk to me now, and there's nothing I can do about it."

"Well, that's bullshit," he stated, cocking his eyebrows slightly.

"Excuse me?!" she gasped. What the hell was he even talking about? How were her personal problems a joke to him? She looked at him incredulously, her blue eyes wide.

"The fact that you think you're stuck in a relationship that makes you unhappy," he met her gaze, twirling the small amount of liquid in his glass, "that's bullshit. Do something about it. Break up with him. Call your mom. Go home. Tada, problem solved."

"It's not that easy," Rory stuttered, surprised at his done-and-done attitude. It wasn't that easy, was it? "I made a commitment to this relationship. I can't bail at the first sign of trouble."

"Why not?" he smirked at her in that innocent, boyish way that most likely got him out of trouble throughout the years. "What do you owe him? You seem to like your family well enough. Why should you sacrifice a relationship with them for a guy you're not happy with?"

"I love him," she said almost to herself, as she stared off across the bar, his words consuming her. Was her love for Jess enough to make them work? She knew she wanted to go back to Yale in the fall and while he said he supported her, she knew he'd much rather her transfer. He didn't want to try long distance. Did he not think they were strong enough? Were they?

And then there was the huge issue of his writing. She could stay with him until the end of the summer, but why should she be in a relationship with a blatant timestamp on it? And even if she did, would it be worth it? He was always working on his novel. She fully respected that and was proud of him, but they would never be able to spend enough time together.

"You should go call your mom," he murmured softly, pulling her out from her internal debate. She looked back at him with confused, wide eyes.

"Right now?" she questioned in a haze.

"Yep," he popped his 'p.' "Don't want to lose your nerve, do you?"

"I don't think I have any nerve to begin with," she grumbled nervously, but slowly getting off her high stool. Was she really going to do this? This idea that a complete stranger made up after only knowing her less than an hour?

She pursed her lips in determination. Yes, she was. She missed her mom. And she wanted to go home.

"It'll be fine," he reassured over his shoulder at her, finishing off the last of his... second drink? She had lost count of the amount of alcohol the consumed.

As she was passing behind him, she briefly hesitated before brushing his shoulder with her fingertips. Her eyes caught his brown ones as he tilted his head toward hers, "thank you. For listening and for giving me the push I needed."

Without waiting for a response, Rory was already out the door of the bar and on the bustling city sidewalk in the sun. Shaking minutely, she took her cell phone out of her purse and pushed speed dial 1. "…. Mom?"