Valarie Gilmore wasn't supposed to end up in Stars Hollow. Nineteen, chain-smoking, working shifts at Luke's and the Dragonfly, and sneaking off to karaoke bars to belt Cher like it's survival-she's the Gilmore girl no one expected. She doesn't fit. Not with Rory, who thinks Val's reckless. Not with the town, who whispers about her late nights and sharp edges. Lorelai's her only anchor, but even that can't cure the ache of being stuck between invisible and misunderstood. Then Jess Mariano shows up-Luke's brooding nephew with a chip on his shoulder and a smirk that cuts too deep. From the moment they meet, it's war: insults, sabotage, and sparks they both pretend to hate. But Jess sees through Val in ways no one else dares. And the more he pushes, the more she pushes back-until the line between enemy and something far more dangerous starts to blur. Messy, raw, and addictive, The Extra Gilmore is a mature reimagining set during Gilmore Girls Season 2: a slow-burn, enemies-to-lovers story about finding your place, losing control, and the one person you can't stand becoming the only one you can't ignore.

Missing a piece of herself she knows will never be replaced, Ella Stevens can only hope to earn some extra money waitressing at Luke's Diner. When Jess Mariano, Luke's New Yorker nephew and the new teen menace of Stars Hollow, arrives in town, it quickly becomes clear he has no plans to make her life any easier. As time goes on, neither of them prove quite as they appear. JessxOC

˗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.

Cleo Ashford wasn't exactly Stars Hollow's sweetheart - and she never tried to be. You didn't need to be a mind reader or some psychic tarot-reading town weirdo to figure out why Mrs. Kim practically hissed like a vampire at the sight of her near Lane. Why Babette's muttering turned into full-on commentary the second Cleo's combat boots hit the pavement. Or why Luke Danes, king of grumpy coffee slinging, could suddenly remember a dozen "fire code violations" every time Cleo asked if he was hiring. People didn't like her. Fine. Cool. Cute, even. Let them clutch their pearls while she smoked in the alley behind Doose's and rolled her eyes through yet another town meeting where Taylor tried to ban fun. Cleo wasn't interested in fitting in with the cookie-cutter charm of this postcard town. She wasn't interested in validation, approval, or any of the suffocating politeness the residents used like a weapon. She had a plan - get out. Leave Stars Hollow choking on her exhaust. As soon as her mom stopped pretending she could "fix her" with therapy pamphlets and curfews, Cleo was gone. One-way ticket. New life. No strings. But then he showed up. Luke's nephew. Broody, smug, eyes like he knew things he had no business knowing. A boy who didn't look at her like she was trouble - he looked at her like he wanted to get in trouble with her. And that? That was a problem. A distraction. An anchor. Now, it wasn't just her mother trying to chain her to this town. It was him, too. And Cleo Ashford didn't do chains.

.𖥔 ݁ ˖ִ ࣪⚝₊ ⊹˚ Tell me a lie. Whisper it soft enough that I almost believe you. Call it love if you want or don't call it anything at all. Just kiss me in the dark and let me forget my own name by the time the sun comes up. Because this isn't forever. It can't be. We can get drunk on wandering hands and stolen cigarettes, on insults that sound like affection, on silences that stretch too long to be safe. And tomorrow, when it hurts less to pretend, we'll act like none of it mattered. We'll shrug, we'll smirk, we'll turn away. You'll throw your cards on the table (sarcasm, smirk, shoulder shrug) and I'll follow, reckless as always, even though we both know the ending. You'll let me. Because that's what you do: you let me, even when it costs you. Break my heart, or I'll break yours first. Either way, it was always going to end like this. Because somewhere out there, there's a blonde other. The ghost I'll always run back to. And you - you'll know it. You'll see it. You'll let it happen anyway, because for whatever little time we have, it's still real. And when it's over, you won't say you told me so. You'll just light another cigarette, watch me walk away and wear that look; the one that says you knew all along. But until then? Kiss me in the dark. gilmore girls oc x jess mariano & tristan dugray season 2 - onwards (smut warning!)

When Erika Anderson moves to Stars Hollow, the last thing she expects is him - Jess Mariano. He's sarcastic, impossible, and infuriatingly good at getting under her skin. She's stubborn, sharp-tongued, and way too good at giving it right back. They argue about everything - books, coffee, life - until one day, the line between hate and something far more dangerous starts to blur. Because sometimes the person you can't stand is the one you can't stay away from. SETTING: Gilmore Girls (season 2-6) RANKINGS: #1 in #gilmoregirls

Jess Mariano X OC Undecided Characters name has been homeschooled all her life. Locked away from the chaotic events of Stars Hallows. All of that changes when her favorite diner owner receives a special visitor. AN: None of my fanfictions have normal descriptions so I tried to write one for this book. I find them low-key cringey, like I don't know how to write a good one 😭😭😭 pls pls read and ignore the description thank you omg 😭😭😭😭🙏🙏🙏

On paper, they were perfect together. She understood him to levels that no one else did and he worked hard to ensure that she could have the future that she deserved - no matter the consequences. They had multitudes of common interests and disagreed on healthy things, not anything too awful. But life often throws curveballs and relationships can never be that perfect depiction, especially when one party of the relationship had far too many thoughts rambling around inside his mind. But when everything in her life seemed to come back to him, how could she avoid him? ​ ❝ Over and over the only truth Everything comes back to you.❞ approx 90k words ~messy relationship (friends to lovers) JESS MARIANO X OC [16 SEP-21 JAN]

❝𝘐 𝘧𝘦𝘦𝘭 𝘮𝘺𝘴𝘦𝘭𝘧 𝘧𝘢𝘭𝘭𝘪𝘯𝘨 𝘧𝘶𝘳𝘵𝘩𝘦𝘳 𝘥𝘰𝘸𝘯 𝘺𝘰𝘶𝘳 𝘱𝘳𝘪𝘰𝘳𝘪𝘵𝘪𝘦𝘴 𝘈𝘯𝘥 𝘐 𝘴𝘵𝘪𝘭𝘭 𝘮𝘢𝘬𝘦 𝘦𝘹𝘤𝘶𝘴𝘦𝘴 𝘧𝘰𝘳 𝘺𝘰𝘶 𝘤𝘰𝘯𝘴𝘵𝘢𝘯𝘵𝘭𝘺 𝘐 𝘸𝘰𝘯𝘥𝘦𝘳 𝘩𝘰𝘸 𝘮𝘢𝘯𝘺 𝘵𝘩𝘪𝘯𝘨𝘴 𝘺𝘰𝘶 𝘵𝘩𝘪𝘯𝘬 𝘢𝘣𝘰𝘶𝘵 𝘣𝘦𝘧𝘰𝘳𝘦 𝘉𝘦𝘧𝘰𝘳𝘦 𝘺𝘰𝘶 𝘨𝘦𝘵 𝘵𝘰 𝘮𝘦❞ 𝐼𝓃 𝓌𝒽𝒾𝒸𝒽, Annalise Gilmore was used to being invisible. Her mother's afterthought. Her sister's shadow. The quiet girl in a loud town. Then Jess Mariano showed up, the boy from New York with too many walls and not enough hope. Two broken souls, orbiting each other in a town that never changes. Together, they might just find the courage to heal. But healing hearts always comes with a price. Jess x fem oc *SLOW UPDATES* I do not own Gilmore Girls. The series belongs to the original author and director. I only own Annalise and any other OC's

↳ ✹ 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-?