This Is My First Time Writing Rory - Tumblr Posts

Opposites Attract

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Notes - This is my first Rory imagine so it’s probably ooc a bit, also I tried to avoid using pronouns just because there isn’t much Rory x reader fanfic so anyone can read this!

Requested - Yes -  @fanboy7794​ - Would you be willing to do a rory x reader, Lorelai hates them and to get rory to break up with them until she sees a sweet moment between them.

You had always been more reckless than most your age, more adventurous, you didn’t really care what other people thought of you and were more than happy with your own company. It was a lot easier to be yourself in a big city like New York, a lot easier to get away with things too but here in small town Stars Hollow, it was the complete opposite of where you wanted to be. The town was too small, too suffocating, everyone knew each other, it was like you couldn’t breathe without everyone knowing.

You’d been in town for a week before the towns people started talking about you. Criticising everything about you; your hair, your dress sense, skipping school, stealing, though they only speculated this they weren’t certain you had, your explicit language. That was just to name a few. 

You hardly showed up to school so hadn’t met many other people your age which you were fine with. It wasn’t until you’d been in town for two weeks or so that you bumped in her; Rory Gilmore. 

You’d snuck out of the house late one night, you didn’t know why your parents even bothered grounding you any more, they knew you would never listen. You were expecting Stars Hollow to be empty so were surprised when you turned a corner and slammed into another person.

“Watch where you’re going.” You snapped.

“I’m so sorry!” You heard a girl exclaim and looked down to see she had dropped a stack of books and a to go cup from Luke’s. You looked at the girl for a moment, feeling a small smirk pull on your lips, her blue eyes caught your attention straight away, they were mesmerising. 

You knelt down to help her pick up some of the books, watching as she looked up at you and smiled shyly.

“I’m Rory Gilmore.” She introduced herself, smiling as you gave her four or so books. “Thank you, I really am sorry, I wasn’t paying attention, I have this exam in two days and I’m just trying to-” She cut herself off with a blush of embarrassment. “Sorry, I’m rambling.” 

“Don’t worry about it.” You smirked, “I’m Y/N.”

“I don’t think I’ve seen you around here before.” She prompted and you resisted the urge to roll your eyes, she was intriguing, yes, but you really weren’t in the mood for making friends.

“Yeah, well, me and my family just moved in.” Was all you said but she was nodding and smiling along. “Well, I won’t keep you from studying,” You said with a look that showed how you felt about that particular activity, you rarely showed up to school, yet alone studied outside of school times, “See you around, Gilmore.” 

“Good night, Y/N!” Rory grinned at you before walking past you, turning around to get one more look at you before disappearing.

For some reason you found yourself hoping you would see her around.

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And see her you did.

The second time you ran into Rory was when you had just finished being followed by Taylor, harassing you over missing money that you definitely had stolen. You saw her go into Luke’s alone and couldn’t resist.

You walked into Luke’s, leaning against the counter, and saw the exact moment she saw you. She smiled shyly as she tucked a strand of hair behind her ear causing you to fight back a smirk. 

“Hey.” She said as she came to stand next to you, you watched as Luke looked between the two of you with a suspicious look.

“Gilmore.” You greeted, nodding your head at her slightly. 

“I’ve never seen you before, now I’ve seen you twice in three days. If I didn’t know any better, I’d say you were following me.” Rory joked causing you to chuckle in amusement. 

“Guess you could say I couldn’t resist.” You said, meeting her gaze. She really was beautiful, her eyes, the way her hair fell just past her shoulders. She was wearing a school uniform today that complemented her well. You knew the local school didn’t have a uniform but didn’t know of any other schools. “What’s with the uniform?” You asked, acting uninterested in her answer but listening to every word she said.

“Oh, I go to Chilton.” At your raised eyebrow she clarified, “It’s a private school up in Hartford.” 

“Private school, you must be pretty damn smart then.” You acknowledge, watching her as she nodded in agreement. The fact she knew she was smart and owned it made her even more attractive. 

“Rory!” You heard someone exclaim from the door. You pulled your gaze away from Rory and saw a woman that resembled her making her way over to the two of you. Not missing how she look at you with disdain.

“Hey mom,” Rory greeted, accepting the one-armed hug her mom gave.

“Who’s this?” She asked but from the way she looked at you, you knew she didn’t need an answer.

“Oh, this is Y/N.” Rory explained that you were new in town and how the two of you had met the other night. 

“Well I should be going.” You told her before going to leave but turned around to smirk at her when she called your name.

“You didn’t order anything.”

“Like I said,” You grinned, sounding amused, “I couldn’t resist.” And with that you turned and left Luke’s looking through the window as you passed to see Rory’s cheeks flushed red and her mom scowling between the door and her daughter.

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At some point hanging out with Rory became a regular thing for you. You didn’t know how it had happened, just that Rory had come and joined you whenever she saw you and vice versa. At some point you had begun meeting her at the bus stop after she had finished Chilton, she often told you off for skipping school but there wasn’t much heat to her words. Eventually, you talked her into sneaking out of the house. At first it was only to meet up with her in her backyard but over time you’d convinced her to come further out, to the lake, to the centre and had almost convinced her to come on a drive with you though when she saw the bike she shook her head no. 

She accepted the way you were, didn’t try to change you, just poked fun and teased you and overtime you found yourself actually liking being around her, something you hadn’t done with many people. It was strange but something about Rory Gilmore spoke to you. 

It was after two or so months of hanging out with Rory that you finally admitted to yourself that you liked the bookworm. The two of you would sit by the lake til late at night, you listen to her talk about Chilton and Paris and the books she’d read, she spoke of Friday night dinners and drama with Lorelai. You were attracted to her, her mind, the way she articulated things, her beauty. You hadn’t felt like this in a long time, if ever. 

“-and get this, they published my article and it made front page news!” Rory beamed as the two of you were walking towards the lake after you’d picked her up from the bus stop. 

“Told you they would.” You grinned, never having a doubt that she wouldn’t get her article published. 

“Yeah you did.” She said softly as she gave you a shy smile, brushing a strand of hair behind her ear. 

That was a thing that happened a lot between you and Rory. Small, soft looks were traded between the two of you, both of you glancing secretly at the other when you thought they couldn’t see. Smiles with hidden meanings and words that went unspoken were exchanged back and forth. 

“So, what’s next for the great Rory Gilmore?” You smirked knowing that she was getting ready to apply for colleges and stressing out majorly over it even though you had no doubt she could get into any school she wanted. 

You watched in amusement as she let out an over exaggerated sigh, running her hand through her hair messily as the two of you sat on the dock.

“I pretty much have everything written but I’m worried that I don’t have enough extracurricular activities but it’s too late to do anything about it now.” She told you, the words coming out in a rush causing you to raise an eyebrow. “Sorry, I’m just quite nervous. I really want to go to Harvard but apparently my grandparents want me to go to Yale and now it’s a big drama.” She exclaimed. 

You just shrugged at her, never understanding why people did what they thought was best for other people rather than doing what they wanted. You said as much to her causing her to deflate.

“I know but I don’t want to disappoint anyone.” The look on her face caused you to frown and you cupped her cheek before you could really talk yourself out of doing it. You watched as she looked up at you, wide eyes and lips parted slightly.

“Do whatever you want,” You told her, brushing your thumb against her cheek, smiling slightly as she leaned into the touch, “Harvard, Yale, community college, drop out or run away to Paris or wherever it is you wanna go. Do whatever you want.” Without giving it, another thought you leaned down and pressed your lips to hers.

The kiss was hesitant to begin with, a feather-like touch of your lips against hers, giving Rory a chance to pull away if she wanted to. You were close enough to her that you felt her tense up and you were seconds away from pulling away, from apologising but before you could she was returning the kiss, just as hesitant as you, barely a brush of your lips. She pulled away first, blushing as she did. 

“Y/N,” She began but the words seemed to die on her lips as she leaned back in, kissing you with more force this time. What had been just a brush against your lips turned into passionate make out session, your hands cupping her cheeks, hers looped around your neck, playing with your hair. It was quite a few minutes before the two of you pulled away gasping for air.

“Hi.” You whispered as you let your forehead rest on hers. 

“Hi.” She giggled, soft smile on her face.

“I’ve wanted to do that for a while.” You confessed, grinning when she admitted to wanting it too. This was new for you, you weren’t used to being close to very many people, especially not like how you were with Rory, how you wanted to be with Rory.

“Let me take you on a date?” You asked, warmth spreading inside you when she agreed.

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In a town like Stars Hollow news spread like wild fire and the fact that you had been dating Rory for just over two months without anyone finding out was astounding. You knew how much the townspeople cared for the Gilmores and how they kept a closer eye on her when you were around and so you were expecting to get caught as you held her hand or pressed a quick kiss to her lips, you weren’t expecting to get caught like this.

It was just past midnight when you snuck across the garden and quietly tapped against Rory’s window. You smiled as she opened it, every noise sounding amplified as you climbed through and greeted her with a kiss, pulling her close and pressing her against the wall. You felt her kiss back with as much force as you before she smiled into the kiss and pulled back, resting her head against the wall and panting lightly.

“Hello to you too.” She grinned as she let her palms rest on your chest, you smiled back at her before diving in again to pepper kisses from her jawline to her neck, smirking against her skin as she titled her head back for you.

You weren’t surprised when after a few minutes of making out Rory pushed you away. The two of you had never done more than kiss, you knew it was something Rory wasn’t ready for, but you enjoyed how she still blushed beautifully each time the two of you shared a heated kiss.

You flopped down of her bed, watching as she laughed quietly and sat next to you. You wrapped your arm around her shoulder letting her cuddle into your side. The two of you stayed on her bed for well over two hours, talking in whispered voices, laughing quietly desperately trying not to wake Lorelai up and kissing some more. 

It was well after two that you had to leave, you’d already stayed longer than you planned to considering it was a school night, which meant very little to you but Rory insisted she had to go. You were currently laying on top of her, pressing soft kisses against her lips and finally pulled away to pull your shoes on.

“I really have to go now.” You insisted as she sat up next to you. 

You said your goodbyes and shared a handful more of kisses before you climbed out of the window, not thinking anyone would see.

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“Lorelai, there you are, doll!” Babette called from her lawn, waving frantically to Lorelai who was just stepping out of the house.

“Hey Babette, everything ok?” She asked as she met the woman half way.

“You’ll never guess what I saw last night!” She exclaimed, “A kid was sneaking out of your house, now it was dark, doll, but I coulda sworn it was that new kid, Y/N, is it?” She asked before shaking her head. “Anyway, I thought I’d let you know. It was midnight when I first saw Y/N and then saw the kid leaving at two.” 

Lorelai was horrified but she smiled and quickly thanked Babette before storming off, making her way to Luke’s. There was nothing she could do until Rory got home.

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“Hey kid.” Lorelai greeted the moment Rory walked through the door. Rory rounded the corner into the kitchen and threw her bag into her room as she said hi to Lorelai. “So, anything exciting happen since last night?” She asked causing Rory to shoot her a look of confusion.

“Erm, no, just school.” Rory said cautiously, not knowing where this was going but Lorelai was obviously upset over something.

“Oh cool, cool.” Lorelai nodded, staying silent for a few moments before speaking again, “It’s just, this morning I had a really interesting conversation with Babette. Did you know she said she saw some kid that happened to look exactly like Y/N sneaking in and out of our house last night?” 

Rory froze as she reached for a mug, eyes wide and face draining of colour. It was no secret Lorelai didn’t like you, she didn’t realise the extent of just how well the two of you were getting along. Even in public you seemed more like casual acquaintances more than anything. Rory knew there was no way of getting out of this and honestly, she was a little relieved, she hated lying to Lorelai but she hadn’t come up with a good way to tell her about you.

Slowly Rory turned around and faced Lorelai, a sheepish look on her face.

“Before you get mad-” Rory began but was quickly cut off by Lorelai.

“Oh, I’m already mad, in fact, I’m so far past mad, mad looks pretty tame!” Lorelai exclaimed as she stood up, locking eyes with Rory. “How long?” She asked, her tone eerily flat.

“Mom-”

“How long, Rory?” She asked again and watch as Rory screwed her eyes shut before answering.

“A little over two months.” She confessed; voice barely louder than a whisper but in the quiet of the room she may as well of shouted it.

“Two months!?” Lorelai yelled, “That kid, that low life kid, has been sneaking around with you, sneaking into my house, for two months? Why Rory? I mean I know opposites attract but come on, the kid skips school, steals, lies, vandalises property, I mean seriously Rory the list is endless, what are you thinking?”

“I’m thinking you don’t know Y/N, like I do. You don’t see the sides I do, the kind, sweet and caring side. I really like Y/N.” Rory pleaded with Lorelai but she just shook her head.

“I want you to end this, Rory.” Lorelai said leaving no room for argument.

“Please mom.” Rory tried her eyes filling with tears.

“No Rory, end it.” And with that Lorelai turned and went upstairs, leaving Rory in the kitchen with silent tears falling down her face. 

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Rory paced her room as she waited for you to arrive. She had called you a few hours after she had calmed down and asked to see you. You hadn’t thought much of it though you probably should have considering it was only five and she had told you to use the front door.

Her heart felt like it had stopped when she heard a knock on the door and she could see Lorelai looking from her spot on the sofa. With a deep breath she opened the door and stepped out onto the porch. 

“Hey.” She greeted, her tone void of emotion and her eyes still looked red.

“Hey.” You returned softly, stepping closer to cup her cheek and run your thumb against her cheek. She allowed herself to lean into the touch for a moment before pushing you away. “Everything ok?”

“We have to break up.” She managed to say after a long moment of silence. Your eyes widened as you took in what she said.

“Wait, what?” You asked, frowning as you took a step back, looking at her in confusion.

“I’m sorry,” She told you, teary eyes wide as she did, “but we have to break up.”

“Why?” You asked, trying to control your emotions, trying not to let it show how much she was hurting you.

She just shook her head at you. A few tears managed to make their way down her face as she looked at you apologetically. 

“Please, just tell me why.” You tried again but she just shook her head and whispered an apology.  “Rory-” You began but she spoke before you could continue.

“I’m so sorry.” Was all she said before dashing back inside, leaving you looking at the closed front door with tears in your eyes.

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It had been just over a week since your unexpected break up with Rory. In that time, you had taken every opportunity you could to disrupt the town whether it be by stealing from the market, causing such a disruption that the parade couldn’t commence and just generally annoyed the townspeople so much you were the only topic at that week’s town meeting. 

You hated to admit how much it was hurting you that Rory had broken up with you out of the blue without any warning. Sure, you were polar opposites in most ways, she was the straight a student who put school before anything and you would rather skip school and cause a scene but you had plenty in common as well. 

It was nearing on 6pm when you had finally had enough. You at least deserved to know why Rory had broken up with you so you climbed out of your bedroom window with ease and made your way over to her house hoping she was home.

The entire walk over there you thought of every reason she could give and most of them you couldn’t argue with and by the time you got to her window you’d convinced yourself that it was a bad idea, that she could do so much better than you but still, you took a deep breath and knocked quietly on her window. 

You watched as she looked at you in confusion, her eyes seemed a little red around the edges as she opened her window.

“Y/N?” She asked, the crease in between her eyebrows deepening as she titled her head.

“I’m sorry,” You began, not noticing that her bedroom door was open or the fact that Lorelai was stood there listening to everything that was about to be said, “I know you probably don’t want to see me but I have to know why?” You asked, eyes wide as you pleaded with her.

“Y/N.” She sighed, looking down and tugging at the sleeves of her sweater. “I didn’t-” She started but her voice broke, you didn’t need to see her eyes to know they had filled with tears.

“Hey, I’m sorry, I’ll leave but I really like you and I want so badly to be with you but I know you can do so much better, you deserve better and I’m just sorry I couldn’t be that.” Your own voice sounded strained now and you cursed yourself for letting your eyes water up.

Rory’s head snapped up as she shook her head, reaching out and grabbing one of your hands.

“Stop it, none of this is your fault.” She cried and you took a step closer, leaning up to wipe away her tears with your free hand. Rory leaned down and pressed your foreheads together. “My mom doesn’t like you and she said I had to break up with you, I’m so sorry.” 

Out of all the reasons you thought she would give you this wasn’t it. Though a part of you should have probably considered it considering how close she was with her mom. 

You heard yourself laugh in disbelief before shaking your head.

“I can’t convince you to get back with me, much as I want to I know how close your mom and you are and I don’t want to be the one to come between that but Rory Gilmore I like you, I like you a lot and-” You were cut off by Rory leaning down to kiss you, it was messy and uncoordinated but right and perfect. You allowed yourself a few moments to just kiss her back, to have her this close before you regretfully pulled away from her.  

“I’m sorry.” She mumbled and you let out a watery, unamused chuckled and leaned up to kiss her forehead.

“See you around, Gilmore.” You smiled and it hurt you to pull away from her but you did.

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Lorelai watched as you pulled away from Rory and watched as Rory collapsed down on her bed with tears falling freely down her face. She frowned at the scene in front of her feeling like she had screwed up. Maybe making Rory break up with you was a mistake, maybe she had to let Rory be with somebody like you, honestly it was probably long overdue. She could tell, at least from what she had overheard, that you definitely cared for Rory and that you didn’t want to hurt her. With a sigh Lorelai entered Rory’s room and sat down next to her crying daughter, wrapping an arm around her and pulling her close.

“Listen kid, if you wanna be with Y/N, that’s fine. I might not like it but if it makes you happy then what I say doesn’t matter and if it does end badly, well that’s what ice cream and movies are for.” She smiled. 

Rory looked up at her with wet, hopeful eyes and hesitantly asked if she was sure. As much as she liked you, she didn’t want to do anything to disrupt their dynamic. 

“I’m sure, kid.” Lorelai reassured, sure she might not be your biggest fan but you made her daughter happy and at the end of the day that’s all she could ask for.

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You were at Luke’s the next morning, sipping on your drink as you tried to keep your eyes open. You couldn’t sleep last night no matter how much you tried, you just kept tossing and turning.

Thankfully nobody bothered you and you were able to enjoy your drink in peace. You didn’t bother looking up when you heard the door open and rolled your eyes when you heard someone pull the chair across from you out. 

“Piss off.” You snapped but your head shot up when you heard Rory. 

“Hi.” She spoke hesitantly. “I’m sorry, I shouldn’t have broken up with you just because of my mom, it was wrong and I’m sorry.”

“I get it, ok, you and your mom are close.” You told her and meant it, you knew story and her mom where close, had been their whole lives and you knew you never stood a chance the moment Lorelai found out. 

“My mom came and spoke to me last night after you left and she said it was ok if we dated. She doesn’t love it but she’s willingly to give it a chance.” Rory told you with a small smile on her face, nervous for your reaction. 

You looked at her blankly for a moment before a smile worked its way onto your face. 

“Seriously?” You asked and she nodded, her own smile widening. 

“Yeah, I really am sorry for all this though.” You just rolled your eyes at her before telling her to come with you, pulling her out of the seat and tugging her after you.

You led Rory over towards the lake, the two of you sitting on the dock, looking out at the water. 

“So, we’re really ok?” You asked just to check, wanting to confirm it. Rory smiled at you, leaning forward to cup your cheek. 

“We’re ok.” She reassured and with that you leaned forward, pressing your lips against hers in a hard and passionate kiss that showed just how much you had missed her.