Author's Note: I had so many thoughts running through my head after watching (the sublime) Fall episode of Gilmore Girls: Year in the Life. In my head, Jess is Rory's "Luke," and it's only a matter of time before she realizes it. This fic will be a series of important moments in Rory and Jess's friendship, each one gradually building to a realization that the perfect person for the other is right in front of them. (Important to note there will be NO Logan bashing in this story. He's not my favorite character, but my love of Matt won't stand for any fictional abuse of his character.)

It was the perfect day for a wedding.

The sun was shining while the crisp fall air ruffled the changing leaves overhead, and almost everyone from Star's Hollow was milling around in the cheery sunlight, having showed up to witness the (second) wedding between the beloved diner owner and inn keeper. The day couldn't have been more ideal if it had been personally planned and organized by the great Emily Gilmore herself.

Rory wished she could focus on that fact rather than the unexpected development that had reared its head in her life a few days earlier. Pushing the still full glass of celebratory champagne away from her, she recalled the brief conversation with her mother earlier that morning.

"Mom?"

"Yeah."

"I'm pregnant."

Lorelai sat in stunned silence for a few moments, absorbing the shock of her daughter's bald statement. "Full freakin' circle," she muttered a few seconds later under her breath, seemingly at a loss to say anything else.

After a few seconds more of careful thought, she caught Rory's hands up in her own and said the most perfectly Lorelai Gilmore thing that Rory needed to hear in that moment. "I'm here for you, kid. Always." Her eyes started to tear up then, and she had to take a deep breath in order to finish her thought. "I know it's scary, but no matter what happens, I'm here."

Rory felt the hot tears she had been holding in since the shock of her discovery roll down her cheeks as she pulled her mother to her. Her rock. Her fortress. "I love you, Mom."

"Love you too, kid."

Pushing the stem of her champagne flute across the linen covered table, Rory watched the fall sunshine sparkle through the liquid, and a smile formed on her face as she thought of her mother. No matter what happened, no matter how many petty fights or major argument they might have, she could always depend on her mom. Things always seemed a little less bleak with Lorelai Gilmore on your side.

"Enjoying your lunch I see."

Rory looked up from her drink into the smiling eyes of Jess Mariano. He had shaved since the day before, though his hair hung just as long as before around his ears and neck. He might look a bit rougher in his thirties than he had when he was younger, but the easiness in his stride and smile in his eyes were the more stark contrast to that young angry boy that had fascinated her years ago.

Jess's eyes squinted together in confusion as hers drifted off into the past. "Hey," he waved his hand playfully in front of her face, "you still there? How many lunches have you had so far?" He eyed her glass with exaggerated suspiciousness.

She laughed at his joke, shaking her head in denial. "None, actually. Taylor promised free ice cream later, so I'm saving up all my room for that. He's got a new flavor, chocolate bacon. Sounds very promising." Pushing the glass further out of reach, she waved him to sit next to her.

"Well I can see why you wouldn't want to miss that," he joked after taking a seat. He turned to look at her and squinted his eyes again, taking in the far away look on her face. "You ok? I'll be honest, I thought you'd be a little more peppy after finishing those first three chapters. Which, by the way, I hope I get that chance to look at later. It was a little hard to read with the pages just dangling in front of my face."

He gave her a playful shove, and she pushed back with an indulgent smile stretching her lips. "Sure thing. They're back at the house if you want to come by later. I need an honest opinion on them since Mom refused to read it until it's all finished."

"I can see why she'd say that," Jess agreed with a solemn nod. "It's hard to be objective about something you're too close to." He paused for a second as a thought hit him. "How close is this to your personal life?"

Rory knew where he was going with this line of questioning. "I'll be as kind as possible."

"Don't be kind, Rory," he cut off her explanation with a shake of his head. "Be honest. It reads better." She hesitated to respond after that, and he continued. "I know how much of an ass I was back then. It's not like it'll come as a big shock when I read about it on paper."

"You're so different now than back then," she finally spoke again. "I almost feel bad about bringing it back up."

Jess reached out to give her hand a quick squeeze. "Don't," he repeated his request. "I was an angry kid. Unlike you, I let my life turn me into someone I didn't even like myself. Maybe someone else can learn from my mistakes."

His words pricked a worry inside her chest that had been lying dormant since his arrival at her table. "How did you stop being angry?" The question came out with a tensely rushed statement, throwing off the friendly, easy-going vibe of their conversation up until that point.

If Jess noticed her change in mood, he didn't mention it. Instead he just answered her question. "I had to realize that being angry didn't make anything better. There were people in my life who actually cared about me and wanted me. I had to accept what my life was and make the best of it. Hating the world doesn't make it any easier to live in."

His answer seemed to set her a little more at ease, but a line of worry still creased her forehead. "Rory," Jess covered her hand again, a platonic but comforting gesture. "What's wrong?"

She stared at his strong, tanned hand covering her soft, pale one, keeping her eyes there instead of on his face. She didn't know why the words left her mouth. It wasn't as if she and Jess were even the closest of friends any more, though she felt a comfortable rapport with him that was hard to explain after the history they shared together. The truth was, she felt safe with him, a fact that prompted her to confess something she wouldn't have even thought of mentioning to anyone else. For some crazy reason, she felt like she could confide in him.

"I'm pregnant."

The confession was soft now, not as loud and confident as before. Almost as if the time that had passed between now and this morning had made it less true than before. She kept staring down as she kept talking. "I'm going to raise it on my own, like my mom raised me."

To Jess's credit, he didn't ask the most obvious question, a question she had no intention of answering right now any way, maybe not ever. Instead, like he always did, he got right to the root of the problem. "You're wondering if you can do it on your own."

She nodded her head, still focusing her eyes on their hands atop the table. "You're Rory Gilmore." The fondness in his voice prompted her to look up. The eyes that had been filled with friendly laughter now graced her with affectionate warmth. "You can do anything."

For some reason, his confidence in her threatened to bring back the tears she had shed on her mother's shoulder that morning. "I'm the girl who can't even afford underwear. Remember?"

His grip on her hand tightened as he emphasized his point. "I remember you're the girl who made it into one of the best colleges in the country, worked on the campaign for the President of the United States, and spent the last ten years doing what she loved. You're the girl who's writing the country's next bestseller. If you can do all of that, Rory, you can do this."

"You don't know that," Rory shook her head, attempting to pull her hand back from the warm comfort of his fingers.

He prevented her attempt, keeping her still so he could make her believe his words. "I know you."

"You just admitted yourself that you spent the first half of your life being angry about it. How do I know - ?" she stopped the sentence before the words could do their damage, but he understood her meaning well enough.

"What if your kid turns out like me?" he finished her question for her. The smirk on his face told her he wasn't angry about the comparison of her unborn child to him. "Are you saying you would be disappointed if the next Gilmore turned out to be this amazing?" Jess gestured to himself in mock offense.

"I'm saying I'm afraid I won't be enough to make it happy." Referring to the baby as "it" still made the situation seem like a dream rather than the reality it was.

Jess leaned back in the chair, assessing her with a fond look. "You'd be enough to make anyone happy, Rory. And if I have to harass you with phone calls on an annoyingly regular basis to remind you of that, then I guess that's just what I'll have to do."

She still wasn't as entirely convinced of her mothering skills as Jess but decided to let the subject rest for the moment. "On the topic of helpful advice, I do want your help with something, though it's not about babies." Jess let the subject change without comment. "Since you've always been so honest with me, I'm going to need that on an annoyingly regular basis while I write this book," she said, using his own words. "I need an editor who's close enough to this story to have an accurate perspective but far enough away to view things objectively."

Jess grinned, catching her meaning. "Rory Gilmore, are you asking me to be your editor?"

"Yes, Jess Mariano, I most definitely am."

"Well, my fees are astronomical, but I'll give you the old friends' discount," he answered, brows lifted playfully.

In moments like this, with his handsome face relaxed with the happiness that only peace in life can bring, Rory found herself marveling that this was the same boy who used to walk around like he carried the weight of the world on his shoulders, always lashing out at those closest to him who tried their best to relieve him of it.

Turned out, it was only something he could come to terms with himself, and she was glad he did. That angry bad boy might have been the stuff teenage fantasies are made of, but this joking, confident man in front of her was the friend she wanted in life for the long haul.

"Then it's a deal, Mr. Perkins." She extended her hand to seal the bargain.

He shook it before asking, "If I'm Perkins, then who are you in this scenario, Hemmingway or Fitzgerald? I have to be honest, I was getting kind of used to Roundbottom."

She rolled her eyes without dignifying his reminder about her position on the Stars Hollow Gazette with a response. "Don't you have a best man speech to give?"

"My work is never done," he sighed, getting up to head to the table where Taylor was studiously overseeing every last detail of their last-minute, perfect-fall wedding. "Hey, Rory," he turned back briefly before heading to perform his duties, "If you need anything, anything at all. Just let me know."

As she watched him walk away, Rory sensed his offer had extended past just giving advice on her book, and she appreciated him all the more for the effort.

Lifting her closed lids up toward the warm rays of sun and cradling the worrisome life inside her belly, she said to no one in particular, "Louis, I think this is the beginning of a beautiful friendship."