A/N: I don't quite know where I'm going with this. This is born out of many a discussion on the Gilmore Girls subreddit surrounding our dear Rory and the progression of her personality. I think we can all agree that a tragedy of Rory and Jess is timing and so I wonder what could come about if we live in a world where that's not necessarily an issue?

This story takes place in at the end of season 4 but it's AU where 1. Rory and Jess have not met up until this point and 2. Jess is older (22 or 23, I haven't decided to be honest). But if you want a sense of where he's at, think of our boy at season 6.

Your feedback is always appreciated, let me know if I'm absolutely insane especially because this is getting me back into the fic writing game.

Jess felt he was getting soft in his old age.

5 years ago you could not have paid him to be here walking his crazy mother down the aisle towards her equally crazy and kind of dimwitted husband but he supposes that now change is good. He certainly has every right to stay angry at Liz for the rest of his life. She was never the greatest mother and spent more time high and drunk with a string of men than any on his well being. When he was 18 and able to run off to do his own thing he set off to figure out what his life was supposed to look like. Fuck graduating from high school since he didn't like going anyway. Instead he figured out where his biological father lived and set off on a road trip to California from New York City the day after he turned 18. He wanted answers and once he got those answers he would figure it from there.

Venice Beach was nothing he wanted. He was a complete fish out of water from the sand creeping up his into his dark jeans to the heat stifling him in the leather jacket he didn't go anywhere without. And when he eventually found his father Jimmy Mariano, he also found a warm and sarcastic pseudo stepmother named Sasha and an 11 year old hiding expert bookworm named Lily.

He was pissed at first.

Jimmy had the gall to not even stick around long enough to cut the umbilical cord when he was born, but he had time to give Lily a nickname that he affectionately called her while ruffling her hair? It was maddening. But at least Jimmy looked guilty about it.

He worked at the hot dog stand that spring and summer, saving money to make it back east. He picked Lily up from school everyday and would read with her on the boardwalk. He helped Sasha feed the dogs at night even though about 3 of them always seemed to almost bite his hand off. He and Jimmy would never be perfect and there would never be full forgiveness but he got his answers. And he also got his inspiration.

He wrote The Subsect during that time in California. He would usually end up on the beach at night which was the only time he would even consider it to be worth it. It felt like therapy and as corny as it sounds the anger and resentment slowly resolved itself the more he wrote on the pages of his notebook. By the end of the summer he had finished it and he felt like his time on the West Coast was over.

His goodbye to Jimmy was simple, Sasha made him promise to come and visit again within the next year, and Lily made him promise to mention her whenever he got his book published. He didn't think it was going to happen at the time, but when it did he kept his promise.

Jess traveled through the United States again back to the east coast and plotted his next move. Once he reached Chicago he knew 2 things: New York was not only expensive but also full of memories good and bad that he didn't know he could move beyond if he went back there. His mother was there and that in and of itself was a motivator to stay the hell away. 2. New York was expensive and he had to be at least a little realistic about his prospects. He didn't have his high school diploma and at best could be doing odd jobs to make ends meet. He needed a city that was for sure but he also needed to live.

So he headed to Philadelphia.

He found a cheap place in South Philly and started working in a diner during the day and a bar at night. The bar is where he met Matt and Chris.

The two of them showed up to South Philly Taproom a few times a week to shoot the shit and bug the hell out of Jess. They knew right away that he was not only new to the bar but also to the city so they took great joy in annoying the hell out of him and citing it as his initiation. Eventually he started biting back and they enjoyed his wit so they invited him to sit down with them during his break. From there they told him all about the small publishing house they started on Locust St in Fitler Square. On a whim when drunk with them after his shift he mentioned that he'd written something, an admission they did not forget the next day when they showed up to the Broad Street Diner to hassle him and demand to see his manuscript in hopes that it would be good enough for them to publish it. They followed him everywhere, relentless and unwilling to give until they were able to see what he wrote. He finally relented one night after a shift at SPTR when they followed him back to his apartment and shouted obscenities where he could hear from his window. It was merciful really, his neighbors were so close to coming out there and ending their lives.

They loved it, but Jess still didn't think it was that good. But Chris and Matt didn't seem like the type to dick around on him and just tell him his novel was worth publishing if it wasn't. So they did and hired him to work there along the way. He was able to quit his job at the diner, of course the one he liked least. They printed 500 copies of his book for him to sell at independent bookstores along the coast. It was hard work he would never make a lot of money for, but in the end he was a published author and that meant something.

From that point he built a life in Philadelphia. He continued to work at SPTR for another year until things picked up at Truncheon enough that he could afford to have that be his sole income. He reluctantly accepted that Chris and Matt were his best friends who were determined to break him out of his shells and defenses that were bitterness and resentment. Nights spent at Dirty Franks and other dive bars in the city slowly melted his exterior. He would spend his Saturdays exploring the different neighborhoods in the city, writing his second novel while sitting on the El gaining inspiration from the Mural Arts route. He dated, never wanting to put down long term roots with a girl but slowly finding that he was capable of doing so.

He wasn't perfect, but at 23 he was certainly less angry and was therefore a tad more accepting when his mother called him to tell him she was getting married and needed him to walk her down the aisle.

The wedding was in Stars Hollow, a small town in Connecticut that Liz has threatened to send Jess during his wildest moments until the next morning when she would forget and he would run away to a friend's house for a few days so that she couldn't make good on his promise. As he looks around at the town square and cringes at the overwhelming sense of Pleasantville he gets as he walks around. So far the owner of the market has been eying him as if he's about to start a violent riot and the bigger woman who apparently owns the dance studio eyes him as if she's going to kidnap him and keep him to herself for the rest of his life.

He doesn't really know what to make of it.

The only thing that seems to anchor his experience at this shindig is his Uncle Luke. He remembers him at various times in his life, making visits occasionally but never much of a talker. But now that he's older and calmer he finds it refreshing compared to his mother and wonders about the two of them were even raised together.

He's sitting at the diner waiting for Luke to come downstairs so they can head to the square, rereading a Farewell to Arms when the bell chimes indicating an entrance to the diner. He looks over his shoulder out of curiosity and notices the two women that walk into the diner. The older woman looks to be in her mid to late 30's with long curly brown hair. She chatters away to a younger girl with short brown hair and a pensive look on her face he immediately takes note of. Both women have pink floral wreathes in their hair to match their dresses, probably to match the renaissance theme of this crazy wedding his mother is throwing.

"I just think you have to think twice before even getting in the middle of that situation kid. I mean maybe it's my fault for gossiping about their fights whenever they happen at the inn but gossiping about it in the middle of Doose's where she can hear you? Not cool. They're married and it's his mess now so he has to figure out how to deal with that," he hears the older woman explain quietly.

"I don't want to talk about this with you mom," the younger woman counters.

Jess raises his eyebrows looking at his book. The older woman looks too young to be a mom. Huh.

"Ok ok fine, I'll leave it alone. Just think about what I said."

The two women sit next to him at the counter with the younger girl sitting next to him. He can feel her curious eyes on him but doesn't acknowledge her presence, content to just take notice of her from the corner of his eye for the time being.

She's pretty, looks to be younger than him for sure. Despite the warmth of the sun these days that has already been darkening his complexion, she seems to be avoiding that entirely with her porcelain skin. Her cheeks have a hint of rosiness to them and he can't tell if it's because she's embarrassed for some reason or if it's natural. He is tempted to take a full look at her because of her eyes though since even from his limited vision the blueness of them startles his thoughts and-

"Hemingway huh?"

He looks over quickly at the sound of her voice and is faced immediately with the eyes he was curious to get a good look at. And just as he suspected the immense depth of them almost prevent him from responding properly.

Almost.

"Yeah, Hemingway."

She waits a beat, almost expecting him to continue his thought. When she realizes he's not going to she grimaces.

"Oh…well it's a shame you're wasting your time."

He scoffs. "Wasting my time? I'm guessing you're not a fan of Hemingway?"

"Well if you're into reading a depressing diatribe that will put you to sleep…"

"Oh I see. And what would you give as a counterpoint to a depressing diatribe? What's your Hemingway?" he asks with a smile.

"I have to say that The Fountainhead is a weirdly comforting book to me. Always something to come back to when I'm not quite sure what to read next."

"Oh geeze we clearly have to end this conversation here. Ayn Rand is a political nut," he groans while closing his book.

"Oh come on, that book taught me all about the art of a well written monologue. If you can like Hemingway I think I can appreciate Rand."

"Agree to disagree," Jess concedes.

They stare at each other with smiles on their faces. It's rare that Jess meets a girl that he's able to talk about any literature with even if he doesn't necessarily agree with her choices. It's a refreshing thought.

The older woman looks over at them with a curious look on her face. "You're new," she notices.

"I'm certainly new to you."

"Are you here for the wedding?" the younger girl asks.

"Yeah my mom is the bride of this crackfest," Jess answers.

The older woman's eyes widen. "You're Liz's kid? Oh! You're Jess!"

The younger woman's eyes widen as well. "Oh wow! You're Jess!"

"Well then, apparently I'm not so new to the two of you," he muses.

"Well after all the gushing Liz has done about you and by extension Luke I feel like there's a few things I already know but yes you're still kind of new," the older woman rambles. "I'm Lorelai by the way, I've known your uncle for awhile since I bother him for coffee and sustenance everyday. The Rand fanatic is my daughter Rory."

Rory gives him a small wave with a smile. "It's nice to meet you. Luke mentioned awhile ago that you wrote a book actually! I found it in a bookstore near my school. It was good! Cool to put a face to the book."

Jess ducks his head bashfully, surprised to find that his mother and uncle even talk that much about him.

"It's really not that good, you're being too nice," he murmurs.

"No it was great! The right amount of angst without becoming too overbearing and contrite. Are you writing a sequel?"

"Oh no one needs a sequel. But thanks for asking."

Just then, Luke comes bounding down the stairs and appears in a sharp looking suit. The only thing he's ever seen his uncle in despite their infrequent encounters is flannel and a backwards hat.

Lorelai sits up straighter. "Oh…you look…nice."

Luke looks up adjusting his tie. "Oh hey, you look…you look beautiful."

Jess shakes his head and smirks at how smooth this is going. He looks over at Rory who shares a similar look.

There's a palpable silence that comes over the foursome despite the surrounding noise of the diner that is still operating. Jess decides to do everyone a favor.

"Ok so…I guess we should get going…make sure Liz gets down the aisle I guess?"

Rory nods. "Yeah we should get going, make sure we get good seats!"

Jess, Rory, and Lorelai proceed to get up, gathering their limited belongings and heading towards the entrance with Luke. Luke and Lorelai walk ahead, seeming to engage in short, stinted, and awkward conversation that Jess looks upon with interest. They walk together closely but just far enough that the mood is clearly unsure between them. Rory walks quietly next to him but giggles when she notices the way Jess is looking at the older duo ahead of them.

"This is their first date," she whispers to him.

"Really?" he says with a raise eyebrow.

"Yeah Luke asked her to go with him and we're pretty sure it's a date. They've been dancing around this since I was like 10 so it's kind of a long time coming. I somehow got roped into tagging along since I came back from school this morning."

Jess laughs at the explanation. "So you're third wheeling your mother's first date with my uncle. I'm sorry for you."

Rory shrugs. "It's cool. I mean there's always a ton of people to talk to around here since this is home for me. Plus I figured with it be a renaissance theme there's totally going to be some great entertainment factor."

Jess rolls his eyes. "I'll say. I already had a guy tell me all about how prison totally prepared him for his stint on the circuit last night at the rehearsal dinner."

Rory giggles. "I'll make sure to find him for a good talk later then."

Jess smiles, "I'm sure he'll show you a good time. We can create a signal in case you need saving."

"Hemingway could be our safe word, Lord knows I wouldn't be spouting off about him if I didn't need help."

"Yeah I'll definitely come running when I hear that," he chuckles as the reach the square. "I have to go over to Ms. Patty's and meet my mom there. Walking her down the aisle."

"Oh," Rory notes disappointed. "Well…I'll see at the reception I guess?"

He nods. "Yeah I have to save you from potentially dangerous conversations remember?"

The promise to potentially find her again brings the smile back to her face. "Yeah of course. I'll see you there!"

Rory trails off with her mother and Luke, taking a second look back at Jess as she goes but he is already heading over to Ms. Patty's.

He walks towards the dance studio and laughs to himself. She's definitely younger than him but certainly mature if she can bring up Rand and Hemingway in a debate. She's certainly pretty, not the type he would usually go for but her eyes and natural innocence are not something he has encountered in his life thus far.

He greets his mother with at least half a smile instead of a grimace, because even though this whole wedding is ridiculous, he at least knows he'll be in great company to be able to get through the reception.