Super silly cutesy Jess fanfiction 😝 Rory has a step sister 😱 What will happen 😱😱 (Idk what to write for a description please read 🙏🙏🙏) Warning: over the top silliness please don't take to seriously lol 😝😝

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. DISCLAIMERS: REWRITTEN 3/6/26 (COMPLETELY REWORKED PLOT) doesn't entirely follow the GG timeline .ᐟ !𝐟𝐞𝐦 oc x jess mariano ⋆౨ৎ˚ started 3.22.23 ─── finished 1.03.25

" darling, you are... 𝐭𝐡𝐞 𝐨𝐧𝐥𝐲 𝐞𝐱𝐜𝐞𝐩𝐭𝐢𝐨𝐧 „ ᥫ᭡ troubled teen boy forced to move to a small town in connecticut with his uncle... meets the sweetest girl in town. jess mariano x juliet pierce (female oc)

❝ i know exactly what i'm doing ❞ ━━ delilah iver moved to stars hollow a year before rory gilmore started out at chilton, which gave them time to become close friends (while delilah was still attending chilton), delilah needed to get away from her life in hartford, jess mariano was practically forced to go to stars hollow to stay with his uncle, and the only thing that seemed to make it better was the girl who was always either painting while talking at a high speed or drinking coffee (otherwise known as delilah) jess mariano / oc gilmore girls s2 ━ s3 Published ━ june 2025 Completed ━ Story Status ━ ongoing Cover Made By ━ me

Y/n Conklin and Jeremiah Fisher borderline hate each other. There are constant eye rolls and scoffs when the other one is near. But they learn to put it behind them when it comes to their crushes, Conrad and Belly. How could they get the two lovers to like them? Jealousy? Of course. Fake dating is the way to go, well, fake flinging. But in attempts to catch their crushes hearts... they might just catch one another's eye. "𝘐 𝘬𝘯𝘰𝘸 𝘺𝘰𝘶 𝘭𝘪𝘬𝘦 𝘊𝘰𝘯𝘳𝘢𝘥." "𝘐 𝘬𝘯𝘰𝘸 𝘺𝘰𝘶 𝘭𝘪𝘬𝘦 𝘉𝘦𝘭𝘭𝘺." 𝘵𝘳𝘰𝘱𝘦𝘴 ~ . 𝘧𝘢𝘬𝘦 𝘥𝘢𝘵𝘪𝘯𝘨 . 𝘧𝘳𝘪𝘦𝘯𝘦𝘮𝘪𝘦𝘴 𝘵𝘰 𝘭𝘰𝘷𝘦𝘳𝘴 . 𝘣𝘰𝘺 𝘧𝘢𝘭𝘭𝘴 𝘧𝘪𝘳𝘴𝘵 ~ 𝘢 𝘑𝘦𝘳𝘦𝘮𝘪𝘢𝘩 𝘍𝘪𝘴𝘩𝘦𝘳 𝘴𝘵𝘰𝘳𝘺 ~ 𝘑𝘦𝘳𝘦𝘮𝘪𝘢𝘩 𝘹 𝘠/𝘯 #1 - jeremiah (7/25/22) #1 - jeremiahfisher (8/2/22) #1 - tsitp (8/9/22) #1 - thesummeriturnedpretty (8/18/22)

"What do you mean, Jess?" He bit his lip and looked down. "It's like. . .this town is a painting. Like, it's the most beautiful work of art you've ever seen, a thousand times better than the Sisitine Chapel will ever be, but somebody touched the paint while it was drying. Now, that big old amazing painting has a smudge in it. It's not a big smudge, but it's still there, you know? If you really looked at the painting, you'd see one of the shrubs in the foreground was smudged. It's meaningless, but the artist still tries to hide it. It was a mistake." "You should write a book some day, you know?" Said Kendall, a small little giggle escaping her lips. "But, for what it's worth, you're more than a smudge in the foreground to me."

"you've been gilmored." In which, Theodora Gilmore is forced into reconnecting with her mother and sister. [gilmore girls seasons 1-3] [OC x multiple OC]

In 1984, in the hospital, two twin girls were born. One would grow up to go to private schools and be given everything she ever wanted. The other would end up bouncing from foster home to foster home until she leaves at 16 and finds her way to a small town nearby. Parker has never been one to trust easily, and she never wanted to be a part of the world. She reads to escape everything, and smokes because her first foster parents taught her how. But when she ends up in a small town in Connecticut and meets Jess, will that change? *COMPLETED AND NOW BEING EDITED* I don't own any characters other than my OCs *Timeline will be as accurate as possible, but some things might be moved around as I need to advance the story*

❝ Well you know me, running away from my problems is what I do best. ❞ [ oc/oc, jess/oc ] [ gilmore girls: season 2 - season 7 ] [ cover by amanda ] © daisyjohvson