almost perfect | jess mariano
PAIRING — jess mariano x fem!gilmore!reader
REQUEST — Anon - Where Emily and Richard have a kid a year older than Rory (they had her before Lorelai got pregnant with her) and she’s sent to love with Lorelai around the same the same time jess moves to town? And they meet all cutesy and shit 🤭
SUMMARY — you move to stars hollow to live with your sister, lorelai, and end up falling for the one person who understands you - and the one person your sister doesn't like
WARNINGS — angst, familiy arguments, odd family dynamics, confessions, fluff
WORD COUNT — 3,461
NOTES — this idea has had me in a chokehold fr thank you anon
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Moving to a new town and starting your life at a new high school with only two years left before graduation was difficult. But moving into your sister’s town, and going to a school where her daughter was a former student, and everyone already knows who you are, is infinitely worse.
You supposed that being semi-close to Rory as kids was a good thing, because if it weren’t for knowing her and, by extension, knowing Lane, you’d be wandering these halls completely alone, and doubly more confused.
Dean and Lane were angels, helping you with every piece of much needed information on what teachers were good or bad, who to avoid at every chance, and where to not sit during lunch. They promised to do their best to help, but Lane’s mother was as strict as a dictator, and Dean often worked after school, so beyond sitting with them in the classes you happened to share, there wasn’t much they could do.
Still, Rory walked you to the doors before heading off to catch the bus to Chilton, taking extra care to make sure you were okay before leaving. It was nice, the relationship you had with her despite everything.
Lorelai wasn’t too happy that you were staying at theirs, but she understood why you had to leave your parents behind. Or, more realistically, why you were forced to walk out. It’s why she left them 17 years ago.
Despite the age gap between you and your sister, Lorelai was all too aware of why you were born. Of how your parents treated the both of you, and the fact that no child should’ve been raised under the Gilmore name. She was never really close with you, considering you were only a few months older than Rory, but you understood. No 16 year old should be raising a kid while her parents are raising a baby themselves.
But, she was kind enough to open her arms, and redecorate her spare bedroom, to fit you in. She got you a place at Stars Hollow High, settled you in with the townspeople, and did anything in her power to help.
However, there was no helping the bundle of anxiety in your chest as you headed from your locker to homeroom. The school was small, of course. Not small enough to have a graduating class size of under 70 kids, but small enough that people knew who was attached to your last name. Small enough for people to start asking questions.
Homeroom itself was fine. Lane and Dean had different homeroom classes, and people whispered when your name was called during attendance, but everything else was fine. The boy you sat next to seemed entirely unbothered by the environment around him, clutching a pen as he wrote in the margins of the book he carried - On The Road, by Jack Kerouac. Rory had lent the book to you not even two weeks ago, and you mentally appraised him for his literary taste.
Of course, you should’ve known that trouble would’ve found you not long after your first day.
Between second and third period, you’d been standing at your locker, supposedly the one Rory used to inhabit - and one you’d already decorated with stickers of bands and movie references - switching out your books when three girls approached you. You were already not prepared for any unexpected interactions, but these girls spelled trouble, just from the way they were all blonde, pretty and primped at 9am, in a small town high school. You expected it from the Chilton girls, sure, but not here.
“You’re Y/n Gilmore, right?” The one in the middle said, her mouth upturned in something like a grimace.
“Yeah, why?”
“Well we saw you during homeroom and we were wondering,” the girl on the left spoke, her gum popping annoyingly as she chewed on it. “If you’re, like, a Gilmore, does that make you Rory’s sister?”
“Yeah, we didn’t know Rory had a sister.”
“How come we’ve never seen you before? I mean, you both should’ve gone to the same school, right?”
“Oh, my God, are you not her sister? Or were you just like, in rehab or something?”
“Oh my God, are you a drug addict?”
The girls continued to chirp at you, and among themselves, endlessly thinking up possibilities of how you could be Rory’s sister and still not go to Stars Hollow High until now. You didn’t even know they had that much brain power, let alone that they could jump to that far of a conclusion so fast.
Suddenly, from behind you, someone spoke. “Why don’t you girls leave her alone, huh?”
They stopped, almost freakishly in sync, and grimaced at the person behind you.
“Seriously, Barbie, why don’t you go fix your makeup or something.” He scoffed, stepping up to stand beside you. “And honestly, if she was a tweaker, do you really think she’d even be allowed in the school?”
“I-”
“Just go away,” he complained, and the girl in the middle scoffed.
“Whatever, Jess. Just trying to get to know the new girl.” She rolled her eyes.
You didn’t stop yourself from looking at the trio in disbelief. “You sure have a funny way of doing it, then. Why don’t you make up rumours about someone else and leave me the hell out of it. Or have you gotten bored of doing it to everyone else?”
It was amusing, watching the shock make their jaws drop before they managed to saunter away. When you turned to look at the boy who helped save you from that awful experience, you found the person who sat next to you in homeroom.
“Thanks.”
“No problem,” he shrugged, a slight smirk playing on his lips, and you noticed that his hands were shoved in his front pockets. “Trust me, those girls do that to everyone. Y/n, right?”
“That’s me. And you’re Jess.”
“Yep.”
You stood silently for a few moments, staring awkwardly at one another. Just as you opened your mouth to speak, the warning bell rang, and the noise level around you picked up as students rushed to their next classes.
“See you around, Y/n.” And just like that, Jess disappeared into the crowd of students, leaving you to gather your things and head to calculus, one of the few classes you shared with Lane.
It’s been almost two months since you moved to Stars Hollow, and you found that adjusting was a lot easier than you first thought it would be. Despite having Lane and Dean at your side, you also seemed to be one of the lucky few to catch and retain Jess Mariano’s attention. He was, to everyone else, the loner who barely came to class and had no interest in being in the town in the first place; but he seemed to take a liking to you, the reason for which was still unknown to everyone but him.
He was quick to become your best friend, and the only person in town who you gave a detailed description of your family background to. Somehow, the rumours that the girls who forced you into conversation never made it outside of their circle, but at some point the truth about your relationship with the Gilmore girls was spread around town, as you assumed would happen at some point.
Still, no one minded that much, and found that your closeness to Rory and Lorelai meant that you were close to everyone in Stars Hollow. The welcoming warmth and sense of community was something that you had never felt in Hartford.
Jess, of course, found it annoying, but you liked to tease him about it, and you knew he meant well. No one else seemed to want to care about him like you did, like Luke did. Including Lorelai, who was less than pleased that you chose to befriend him out of all the other supposedly stand-up kids in town.
It wasn’t uncommon for you to have Jess over while Lorelai and Rory went to Hartford for Friday night dinners. In fact, it was what you had in mind for your plans as you watched the mother-daughter duo scramble around the house to get ready.
Rory was, as usual, ready to leave exceptionally early, and had bid you a cheerful goodbye as she headed out to the car to wait for her mom, who was marching her way down the stairs while struggling to put in earrings.
Lorelai caught sight of you on the couch, curled up and channel surfing, and smiled. “So, what are your plans for tonight? Partying hard, I hope. Remember my rule, no bikers and no drugs past 8pm.”
“Funny, Lorelai,” you smiled, craning your neck to look at her as she shoved items from the side table into her purse. “I’ll probably just order in and call Jess. He’s never doing anything on Fridays, and it’s better than being alone all night.”
Your sister paused in the hallway, fidgeting movements indicating that she was contemplating something.
“Can I ask you something?”
“Sure, what’s up?”
Lorelai turned fully, and took a few tentative steps toward you. Her iconic awkwardly polite smile stretched across her features, and you looked her up and down. “Why do you hang out with Jess so much? Sweetie, I mean, you’ve gotta see how bad of an influence he is.”
“He’s not a bad influence, Lor. If anything, I’m being a good influence on him.” You said, sitting up straighter, leaning on the arm of the couch to properly face your sister. “Besides, he’s nice. He just doesn’t like a lot of other people in town.”
“So you’re trying to tell me that he’s nice to everyone but you?”
“Yes, and I don’t exactly see what’s wrong with that.”
“Well, hon, I mean, don’t you think that maybe that’s a little, I dunno, odd?” Lorelai suggested, her fluster clearly underlining her tone.
You shrugged. “I don’t think so, no. He’s my best friend.”
“Yes, I know that, but-” Lorelai tapped her foot, trying to find the right words to say. “I think you’re spending too much time with him, Y/n, and I just think it’s gonna end up with you getting hurt somehow.”
“Hurt?” You scoffed. “Lorelai, how in the world would Jess be able to hurt me?”
Lorelai sighed, stepping closer to you. “I think you like him, Y/n. I think you have a crush on him, and I don’t think he likes you back. I just don’t want you to do anything and then end up being heartbroken and losing Jess as a friend.”
You? Having feelings for Jess? It was something you could barely wrap your mind around. Lorelai’s accusations, even if out of some sort of motherly-type concern, were out of line. There was no way you liked Jess like that, right? And besides, even if you did, she didn’t have the right to try to stop you from doing or not doing anything about it.
“Why are you so concerned about this all of a sudden?” You asked, furrowing your brow. “I mean, I’ve been hanging out with Jess one on one for a while, it’s not like all of a sudden I’ll catch feelings for him or something.”
“I understand that, but I’m saying that it seems like you caught feelings a while ago, Y/n.” Lorelai said, exasperation clear in the speed at which she was talking.
You resisted the urge to roll your eyes. Why won’t she just drop it? “I’ve got it handled, Lorelai, please, just leave it be and go to dinner. You’re gonna be late, and you know how much mom hates that. Especially when you’re late.”
Lorelai scoffed. “I have plenty of time before we have to go. Now will you please tell me why you have such an attitude about this? I’m just trying to look out for you. Jess isn’t good for you, and I just want to-”
“I get that Lorelai but I don’t need you to.” You snapped, swiftly getting to your feet. “I don’t need you to protect me, or look out for my best interest, or be motherly toward me. I get that you’re trying to make up for the fact that you couldn’t protect me as a kid and I ended up getting kicked out or whatever, but you’re not my mother.” Your blood was boiling. You didn’t know why, but it seemed that something within you just… snapped. “I don’t need you, Lorelai.” Your words pierced Lorelai’s heart with every bit of enunciation you placed on them.
“And it doesn’t matter what kind of influence Jess is on me, because our mother made sure to ruin me beforehand. You of all people should understand that.”
Lorelai stood, shocked at your outburst. She’d never seen more of herself in someone before, and still, she was heartbroken. Tears brimmed her eyes as she realized that, despite what you just said was more than likely teenage hormones kicking into gear, it was the truth. She tried, as hard as she could, to protect you as a kid. Harder than she tried to get herself out of that house. But she failed, because Rory came first, always. You didn’t need her anymore, not to raise or protect you.
“You’re right,” Lorelai nodded, clearing her throat before blinking away her tears. “You’re too grown up to need me anymore. I just… wanted to make sure you knew I cared. That I was worried. But you don’t need me, so go ahead and make whatever decisions you want to. It’s not on me.”
You watched Lorelai turn and walk out of the house, the door rattling the house as it swung shut. And suddenly, the silence pressed in on you, weighted with the realization of what you’d just done. Months of trying desperately to repair your relationship with Lorelai, of further building your relationship with Rory, only to have it torn down in seconds by your stupid teenage denial and anger.
The weight of your actions came crashing down, and soon you were sitting back on the couch, sobbing into your hands.
You don’t know how long you spent stuck in that spot until the house rattled again, and Jess was calling out to you, telling you what he forced Luke to make for the both of you to eat during your hangout tonight.
Jess barely heard you crying on the couch until the food was on the table and he turned to find you there, back to him, curled into yourself as you sobbed. His voice faded instantly, his legs making long, quick strides in order to reach you as fast as he could. Jess’ mind was a flurry of confusion and worry - you sounded fine when he called you an hour ago.
As soon as you were within reach, Jess’ hand gripped your shoulder, refusing to let himself lose the grasp he had on you even after he manoeuvred himself to sit next to you. He shuffled as close as he could get, and it was those movements that forced your head up from where it rested on your knees, enclosed by your arms wrapping around your legs.
“Hey,” he said, trying his best to soothe you, but Jess wasn’t one to do that sort of thing often. “What’s wrong?”
“I am,” you croaked, followed by a sniffle and a shaking breath. “I’m so stupid, Jess.”
Jess’ hand moved down your shoulder, until it squeezed your forearm comfortingly. “No, you’re not. And you’re obviously not okay. Tell me what happened.”
As soon as the words left his mouth, you shook your head. Telling Jess that you argued with Lorelai over him would just make things worse with her, and telling him it was about your feelings for him would ruin things altogether.
“I can’t.” You said quietly. “It’s nothing you need to worry about, okay, Jess? I was just stupid and it’s my fault, I don’t wanna drag you into this.”
“No, I do have to worry about it, Y/n.” Jess said, his words firm. You could see his brows furrowing, eyes darkening. His emotions were brewing, and you knew you wouldn’t be able to stop it. “You’re my best friend. Hell, you’re my only friend, and I don’t know how you managed to do it, but I care about you. I actually care about someone for once in my life, and it’s you. So tell me what happened, drag me into it, because I… I care.”
You couldn’t help but chuckle a little bit. Sniffling once again, you moved yourself to wipe some tears from your cheeks and put your hand on top of the hand Jess laid on your forearm. You stared at your hands and soaked in his warmth as you spoke. “It was Lorelai, we fought and-”
“Of course it was,” Jess scoffed.
You rolled your eyes. “Jess, just let me-”
“No, she always has something to say about- about everything.” He said.
“Let me finish, please.” When Jess didn’t speak again, you continued. “I told her you and I were gonna hang out for the night and she sort of… well, she mentioned a few things and I got angry and we fought. I was an idiot and I yelled at her for trying to be my mother because she didn’t protect me as a kid and it just… it was a disaster.”
Jess scoffed again, pulling his hand back and scrubbing his face, leaning into the couch. “Of course, she had to say something about you being with me. What, does she think we’re gonna rob a bank as a fun casual activity? I mean, seriously, she’s had it out for me since day one.”
You leaned forward, re-initiating the touch by resting your arm on his shoulder, your hand just barely grazing the back of his neck. “She doesn’t think we’re good for each other. At all. But she’s wrong, I know she is.”
“Me too,” Jess sighed, looking over at you.
The silence that filled the space between you, and your stomach was churning. Lorelai’s words came back to you, and as much as you didn’t want her in your head right now, you knew, deep down, that what she’d said about your feelings for Jess were true.
Before you could stop yourself, you pulled away and the words came tumbling out, awkward and choppy and full of anxiety. “She was right about one thing, though.”
Again, Jess scoffed an almost playful smirk lifting the corners of his lips. “Oh yeah, and what was that?”
“That I… have feelings for you.” You said, following it with an awkward and bashful smile. It was now or never, you supposed. “I mean, I didn’t even realize it until just now so don’t yell at me for keeping it a secret or something but she is right. You’re the only other person besides her and Rory and Luke that I care about and even then I care more about you than them and all I almost ever think or talk about is you and it sucks and I don’t want to keep it to myself. If you don’t want to be friends anymore I understand because it’s weird to have a friend who has feelings for you, trust me, so you can just leave now if you want-”
Jess’ lips crashing onto your own cut off the breathless ramble you had found yourself in. Your brain nearly completely shut down, complete peace silencing all the anxious thoughts in your head as you closed your eyes. By the time you registered that you needed to kiss back, Jess was pulling away, but you refused to let the moment end. He barely made it inches away before you were chasing his lips, placing a hand on his jaw to guide him back to you.
The kiss was simple, but it was as if it sparked something within you, and every nerve in your body felt the emotion within you. You never imagined you’d be kissing a guy like Jess. Hell, you never imagined you’d find someone like him, someone so damn near perfect for you, in your lifetime. But you did, and he was kissing you, and you couldn’t give a damn about what anyone else would think when they found out. Because right now, it was just you and Jess, and no one else knew, and things were almost perfect, and that was what was important.
You’d fix things with Lorelai tomorrow, and you weren’t sure you’d ever truly fix things with your parents; one day you’d try, just not yet. But for right now, all that mattered was yourself and Jess.
forever taglist: @just-here-to-escape-from-reality @mazerunnerrose @theboldandthebootyful @miraclesoflove @queen-asteria04 @heliads
jess mariano taglist: open!
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hey! saw your post about requesting rory! :)
can u do a chilton rory x f!reader?
bunch of fluff in the beginning, rory and r just cuddling (r is smaller by like 5-6 inches) w forehead kisses and all bc yes
then during that time Emily and Richard come by unexpectedly for whatever reason and see them together. they don't approve of it and blah blah blah crying and drama and angst bc yes
it's up to you if you make them all good in the end I don't mind (I feel like they wouldn't b like this or would maybe warm up to the idea? I'm not so sure but I feel like Richard would be more supportive then emily but it's a ff and not canon so make them mean👍)
thank you sm! :) <<<333
Omg love this plot, thanks for requesting <333
Rory x fem! Chilton r
Tw: slight homophobia, yelling, angst, heavy crying, making out
p.s happy ending:))
Times like this, you felt so safe, so protected, like the whole world was at peace. Your head on her chest, your arms snaked around her her waist as her hands played with your hair. Out of nowhere she would kiss your forehead and you would grab her hand and kiss it return.
Both of you just laying on her bed as you watched a random movie.
Afternoons like this were the best, after an exhausting day at Chilton, coming to her house and simply cuddling, then after a long while doing your homework together and of course staying over as Lorelai absolutely loved you.
At one point the movie was getting boring which lead to many kisses on your forehead, so instead of just kissing Rory’s hand back you turned your ear around, resting propping your body up with one of your elbows. You looked into those ocean blue eyes and closed the gap between the two of you.
Rory smiled against your lips which made you almost melt into a puddle. You were about the break the kiss however the blue eyed girl pulled you back in putting her hand on the back of your neck, now your lips moving roughly against each other.
You then moved down to her neck quickly for finding her sweet spot as she let out a hum of pleasure. You made sure to not leave a mark as Lorelai would come soon and you didn’t want her to think you had done it when you hadn’t and weren’t going to soon, you’re relationship was healthy and none of you wanted the other for sex it was only pure love.
After finishing Rory bent her head down to kiss you once again, what the two of you didn’t notice was a very shocked Richard and Emily standing at the door of the room, which apparently you hadn’t heard when it opened.
Emily shrieked as she saw the two of you kissing, she knew you were Rory’s friend and were a very good student at Chilton she never expected this between the two of you.
Hearing a shriek both of you jumped away, leaving you to fall from the bed because of the shock. “Oh my God, grandma grandpa what are you doing here!” Rory exclaimed as she looked at her grandparent with wide eyes, they finally caught her, she had been so careful in keeping her relationship private.
You quickly stood up and straightened out your uniform as you looked at the Gilmores, your parents were good friends with them so you often saw them and they absolutely loved you. However now they had a bewildered look, it was like hatred coming out of their eyes and slowly making your way towards you making a chill go down your spine.
“We just wanted to surprise you, clearly I should be asking what the hell are you doing to my granddaughter!?” Emily answered Rory but now her attention was towards you.
Just like that you froze, Rory picked up your nervousness and took your hand bringing you back to reality. “Grandma.” She said looking over at her “grandpa,” she added now looking at Richard, “the person I’ve been dating this whole time was y/n… I get you’re not used to this type of relationship, but we’re really happy with each other and I hope you can accept us, accept me.” Rory finished, her voice breaking a bit, she was on the verge of crying, she he never been so scared of being accepted.
You carresed her hand with your thumb, hoping to relieve your girlfriend a bit. “No, I will not accept this young girl! A woman is supposed to be with a man not another woman! You’re just confused with friendship !” Emily yelled, this wasn’t right in her eyes, it was crazy.
A few tears came out of Rory’s eyes, how could her own grandma not accept her. “Miss Gilmore, please, I promise what we have is real. I really love your granddaughter and she makes me happy and I make her happy. Please don’t be mad, it’s true love, we just love each other, we can’t control our feelings, love is love…”
“Y/n i have known you for a very long time, I always thought you were a brilliant young girl. I can’t believe you would do this, and raising your voice at me how dare you! I wool speak to your parents about this!” Emily shouted at you anger completely taking over her as Richard just watched, the man wouldn’t even move.
“Hey do not talk to y/n that way! You know what grandma ? If you’re not gonna accept me then leave ! Just leave!” Rory defended you as she shouted back at her grandma pointing towards the door so they would just leave.
“Rory, don’t talk to your grandma that way.” Richard finally spoke up, you looked between Rory and her grandparents not knowing what to do, this was just crazy.
“Hey, hey, what is going on here?” Lorelai asked as walked in with her keys in hand. Thank God for Lorelai’s timing.
As soon as the woman saw her daughters and your puffy eyes she knew what was going on and immediately pushed through Emily and Richard and stood in front of the two girls. “I think you need to leave.” She stated calmly but clearly enraged.
Emily shook her head “Did you know about this? Your daughter and y/n were kissing when we arrived… they’re both girls and they’re dating how can you let tha-“
“Shut up mom. Of course I know about this, Rory and y/n have been going out for a long time now, and I completely accept this. Y/n is soo good for Rory, if you’re not going to accept your own granddaughter for who she loves. Then leave .” Lorelai cut Emily off not likening the way she treated her daughter.
“All of you are a disgrace, we’re leaving” Emily replied enraged, taking Richards hand and turning around. Meanwhile the man looked a bit sadly mouthing a “sorry” as he turned around following his wife’s lead.
The front door was slammed shut and the three girls stood frozen, Rory’s cries was the only thing heard. Y/n placed a kiss to Rory’s head whispering in her ear “I’m so sorry” and then grabbed her backpack.
“I gotta go, they’re gonna tell my parents- I’m sorry thanks for letting me stay over Miss Gilmore”y/n let out, her voice shaky as she made her way to Rory’s door not daring to look back.
“Y/n wait!” Lorelai shouted in hopes of her daughter’s girlfriend coming back but said girl was already outside.
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