˗ˏˋ𝐆𝐈𝐋𝐌𝐎𝐑𝐄 𝐆𝐈𝐑𝐋𝐒'ˎ˗ ✧.* ᥫ᭡ Mackenzie Sinclair ➸ Jess Mariano. Season 2 ──── Season 7.ᐟ ✎ Started: August 2025. (ongoing) ╭──╯ "In a town where nothing changes, he was the one thing she couldn't ignore." Between family obligations and the shadows of a past she'd rather not face, Kenzie finds herself tangled in a world that feels both suffocating and strangely safe. And then there's Jess Mariano, the boy with too many secrets in his eyes and just enough charm to drive her crazy. But sometimes sparks look a lot like fights, and sometimes the people you're determined to push away are the very ones you can't stop thinking about. Because in Stars Hollow, it's never just coffee and late-night walks, it's stolen glances, quiet banter, and the kind of moments that change everything. ❖ ❖ ❖ I do not own the series Gilmore Girls. I own separate characters added into this fanfiction, + there will be changes from the show.

𝐈𝐍 𝐖𝐇𝐈𝐂𝐇 sophomore year was supposed to be the last time they'd ever see each other. but in the hands of fate, anything can happen - even second chances. OR 𝐈𝐍 𝐖𝐇𝐈𝐂𝐇 she wasn't supposed to see the boy who broke her heart ever again. !𝐟𝐞𝐦 oc x jess mariano DISCLAIMER: doesn't entirely follow the GG timeline .ᐟ this book is kinda old i went back a while ago and tried to fix it up as best i could but if you see mistakes just close your eyes.. ⋆౨ৎ˚ started 3.22.23 ─── finished 1.03.25

𝐈𝐧 𝐰𝐡𝐢𝐜𝐡 𝐭𝐡𝐞 𝐆𝐢𝐥𝐦𝐨𝐫𝐞'𝐬 𝐠𝐨𝐥𝐝𝐞𝐧 𝐠𝐢𝐫𝐥 𝐟𝐢𝐧𝐝𝐬 𝐡𝐞𝐫 𝐬𝐨𝐮𝐥𝐦𝐚𝐭𝐞 𝐰𝐢𝐭𝐡𝐢𝐧 𝐚 𝐦𝐨𝐮𝐧𝐭𝐚𝐢𝐧 𝐨𝐟 𝐨𝐛𝐬𝐭𝐚𝐜𝐥𝐞𝐬. ᵒʳ 𝐂𝐡𝐚𝐫𝐥𝐨𝐭𝐭𝐞 𝐆𝐢𝐥𝐦𝐨𝐫𝐞 𝐝𝐢𝐬𝐜𝐨𝐯𝐞𝐫𝐬 𝐡𝐞𝐚𝐫𝐭𝐛𝐫𝐞𝐚𝐤, 𝐬𝐡𝐢𝐟𝐭 𝐢𝐧 𝐟𝐚𝐦𝐢𝐥𝐲 𝐝𝐲𝐧𝐚𝐦𝐢𝐜, 𝐚𝐧𝐝 𝐬𝐨𝐮𝐥 𝐬𝐞𝐚𝐫𝐜𝐡𝐢𝐧𝐠.

"𝖸𝗈𝗎'𝗋𝖾 𝗈𝗇 𝗒𝗈𝗎𝗋 𝗈𝗐𝗇, 𝗄𝗂𝖽, 𝗒𝖾𝖺𝗁 𝗒𝗈𝗎 𝖼𝖺𝗇 𝖿𝖺𝖼𝖾 𝗍𝗁𝗂𝗌, 𝗒𝗈𝗎'𝗋𝖾 𝗈𝗇 𝗒𝗈𝗎𝗋 𝗈𝗐𝗇, 𝗄𝗂𝖽, 𝗒𝗈𝗎 𝖺𝗅𝗐𝖺𝗒𝗌 𝗁𝖺𝗏𝖾 𝖻𝖾𝖾𝗇" Ashley Mariano is the kind of girl parents warn their kids about. She smoked. She drank. She partied like it's a profession. And she dropped out of high school before junior year was half over. To top it all off, she's seventeen years old and five months pregnant - a walking cautionary tale with chipped black nail polish and a sharp tongue. So when her mother finally snapped - worn down by the late nights, the police calls, the growing bump Ashley refused to talk about - she didn't yell. She didn't cry. She just packed a single suitcase, added Jess's name to the return address, and sent them both away. Now, Ashley and her twin brother are on a one-way bus ride to Stars Hollow, Connecticut - the postcard-perfect town their mother once called home, full of cozy sidewalks and nosy neighbors and exactly none of the chaos Ashley is used to. She doesn't know it yet, but the town that seems too small for secrets might just be the one place she can't hide. And maybe-just maybe-that's exactly what she needs.

☆ Female OC x Jess Mariano ☆ Spencer Archer has always had a plan: get good grades, go to college with Rory and Lane, and keep her life as neat and structured as possible. But when Jess Mariano rolls into Stars Hollow with his dog-eared books, bad attitude, and complete disregard for rules, her carefully laid plans start to unravel...

↳ ✹ 𝒉𝒆𝒓 𝒎𝒊𝒙𝒕𝒂𝒑𝒆 frankie jones was the town's "it girl". she was popular, pretty and sweet-unless you piss her off, you will see a bitter side to her. but she wasn't always the brightest girl. frankie's aunt is sookie st. james and she has lived with her since she was 10 when her mom disappeared during the night and was never seen again. did frankie stop smiling? no. she kept on smiling and being herself. she missed her mom, though. now new boy - jess mariano, luke danes' nephew arrives into town. frankie felt a weird feeling in her stomach whenever shes around him. so, when he starts talking to her-frankie jones begins to act out with him. the town's it girl was in love. jess mariano, 𝒈𝒊𝒍𝒎𝒐𝒓𝒆 𝒈𝒊𝒓𝒍𝒔 season 2-?

"He was a cad, wanted her bad Just like any good trophy hunter And she likes the way it tastes Taming a bear, making him care Watching him jump then pulling him under" Stella has spent her entire life in Stars Hollow, working at Luke's Diner since she was 14. With an absent father and a mother who drowns herself in work and alcohol, Stella has had to take on the role of caretaker for her brilliant but young sister, Blair. The two sisters find comfort and support in Lorelai and Rory, who welcome them into their movie nights and treat them like family. When Jess moves to town, he and Stella initially clash-he's always in her way at work and never pulls his weight. But over time, their shared love of literature and art brings them together, forging a deeper connection than either of them expected. Jess Mariano x OCgirl

𝐢𝐧 𝐰𝐡𝐢𝐜𝐡 Olive Quinn will find in Jess Mariano everything she's always dreamt of.

SMUT WARNING Jess Mariano is not at all thrilled about moving to Stars Hollow, Connecticut, he'd much prefer to go on with his life in the big Apple. He figured that he would absolutely despise the small town life, but after meeting Ivey Gilmore he realized it may not be so bad.

If she had an opinion, she wouldn't hesitate to share it with you. If she wanted something, she would find a way to get it. From the way her eyes lit up when she would talk about the latest book she had read to the bright smile on her face when she was working behind the counter at Luke's, the girl was passionate in the things she did and it was obvious to the people around her. Avery Gilmore is Undefinable. Avery Gilmore is Limitless.