Gilmore Girls X Reader - Tumblr Posts

Why Can’t This Be Real? (Part One)

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Click Here For Part Two - I’m So Glad This is Real.

Requested - Yes - Can you do a Dean Forester x reader fake dating au? Like after Dean and Rory broke up Jess broke up with the reader, then Rory started dating Jess and the reader and Dean were both really hurt, and they start fake dating to spite Rory and Jess (and give Stars hollow something to really gossip about) but things are going really well and they end up helping each other get full scholarships and at some point Dean is like "fuck it, I accidentally fell in love with u, can we date for real?" 

Prompts - Fake dating

You had to admit that you weren’t all too shocked when Jess left you for Rory after the dramatic breakup between Rory and Dean. You were there to witness Dean finally lose his temper and snap, you couldn’t blame him, Rory clearly knew she had feelings for Jess but continued dragging Dean along because Jess was otherwise occupied. Though you hated what Jess had done to you, leaving you feeling used, there was a part of you that still wanted him back.

Maybe that was the reason for this quite frankly insane plan you and Dean had come up with. The two of you had only spoken a hand full of times, Rory wasn’t exactly your biggest fan to begin with and then Jess began hating Dean, there just hadn’t been a good opportunity since he came to the small town of Stars Hollow but now there was. The two of you had pretty much all your classes together and you watched as Dean came in, looking about as good as you felt. The lack of sleep was clearly visible and he just radiated sadness, the same went for you though. Along with the sadness and hurt both of you felt, there was also a deep feeling of embarrassment, both break ups had been rather public and of course gossip spread like wild fire in a town like this.

“Hey Y/N.” Dean had shocked you one day by joining you under a shaded tree that hid you rather well from the rest of the school. Dean had smiled at you confused expression before asking if he could join you.

“Hi Dean, um, yeah, sure.” You’d manage to reply, honestly confused as to why the ex-boyfriend of your ex-boyfriends girlfriend would want to talk to you.

“Listen, I just wanted to say I know how you’re feeling. It sucks, right, but if you ever need to talk to someone, someone who won’t use it as gossip and have it around the town within the hour then just know I’m here.”

That’s how it started. The sincerity in his voice had you believing him and it wasn’t long before you two were sat under the tree hashing out the details.

“Hold on, you want us to fake date?” You’d asked when he brought the idea up one break time.

“I just think that it’ll get some sort of reaction out of them, make them jealous. I mean Rory doesn’t like you and Jess, well we all know how he feels about me.” Dean said with a sarcastic laugh, causing you to smile. “Say no if you want to but I don’t know, it could be interesting.”

“Dean,” You began, upon first hearing the idea it was absurd but the more you thought about how much Jess and Rory had hurt you two, the more it seemed like a good idea. “Let me think about it?” You asked causing him to nod immediately.

“Of course, please take your time. I’ll see you later, Y/N.” You watched as Dean walked away with a slight frown on your face as you thought about what he had said.

-

-

-

It was a week before you’d talk to Dean again. You hadn’t planned on talking to him but you saw him through the window of Luke’s alone and made up your mind then and there.

“May I join you?” You asked as you made your way over to him. Dean looked up from the work he was doing in surprise, only to smile a moment later.

“Y/N! Yes, please have a seat.” He said, gesturing to the seat opposite him.

“What can I get for you, Y/N?” Luke asked before you had the chance to open your mouth. You quickly ordered your regular and turned back to Dean as Luke left.

“So, what’s up?” He asked, fiddling with his pen.

“I’ll be your fake girlfriend.” You told him quietly with a grin. He looked at you for a moment as if working out whether you were being honest before he grinned back at you.

Luke brought you your drink and quickly filled Dean’s up before leaving and before you knew it two and a half hours had passed and you and Dean were still sat in the diner, getting to know one another.

It struck you that Jess had never bothered to get to know the little things about you that Dean was asking about but you pushed that thought from your mind as quickly as it had come.

“Well I should probably go, I didn’t mean to stay this long and I still have that English homework to get done.” You groaned causing Dean to laugh.

“C’mon, I’ll walk you out. I’ve got work anyway.”

As luck would have it as the two of you rounded the corner, Lorelai and Rory nearly walked into you. Whilst Lorelai apologised, you and Dean doing the same, Rory just looked between you and Dean before settling on a glare.

“Well that went well.” You laughed once the pair walked into Luke’s, Dean laughing along with you. “I’ll see you tomorrow then, yeah?” You asked.

“Yeah. You want to meet up here and get some coffee before school?”

“I’d love to.” With that the two of you went your separate ways not noticing the glare Rory was giving you from the diner.

-

-

-

“Did you hear the news?” Babette asked Lorelai one morning, two weeks after you and Dean agreed to fake date.

“No, what news?” Lorelai asked as she leaned against the counter at Luke’s. Luke listened too though not making it obvious and Jess glanced over from were he was talking to Rory.

“Well,” Babette started with a hesitant look towards the young couple, “I heard from Patty, who heard from Joe, who heard from Tom, that Dean and Y/N are dating! I mean can you believe it!” She exclaimed, not noticing the dark look on Rory’s face and the eye roll and mask of indifference on Jess’.

“Wait, Y/N and Dean? As in Rory’s ex boyfriend and Jess’ ex girlfriend?” Lorelai asked, shock clear in her voice.

“Oh my thoughts exactly, doll, I mean who’d have thought it? Anyway, I gotta go, Morey’s expecting me back any moment. See you soon sugars.” And with that Babette left, leaving everyone with different thoughts running through their heads.

-

-

-

Dean and you were sat in Luke’s, both noting how Jess glared at the two of you and pointedly ignored your table. Luke rolled his eyes before taking your orders.

Dean had told you on your walk over to Luke’s about how Rory had shown up at his window, how her apology seemed self-centred and how Rory said she loved him. Dean had sent her away, furious at her for even showing up.

You couldn’t blame him for his anger, especially not when Jess had cornered you when you were leaving the market spouting all the right words of how much he liked you, how Dean was no good.

It was safe to say the urge to slap him was real. How dare he say Dean was no good for you when he ditched you the moment Rory left Dean.

“So, were are we up to?” Dean asked as he moved his chair closer to you, neither of you noticing Rory, Lorelai and Sookie entering the diner and sitting at the opposite end.

“Ugh math.” You told him with a grimace. The two of you were taking this extra time together to help each other with school work, focusing on topics the other wasn’t so good at and teaching it until it made sense.

You had helped Dean with English and science, helping to come up with easy ways to memorise important passages of texts or formulas. Whereas Dean was helping you with math, the one subject that you needed to raise your grade in order to even have a chance at the colleges you were looking at.

Dean had confided in you he hadn’t thought much about college, not knowing what he wanted to do. You in turn helped him research different colleges and he eventually found a few with courses that interested him. Now that you both had a vague idea of what you wanted it was easy to set targets and help each other.

“C’mon now,” Dean laughed, wrapping his arm around you as you pressed your forehead to his shoulder with a groan, “you’re getting better.”

“No I’m not. I’m gonna fail, there’s no hope.” You pouted over dramatically causing him to laugh louder before pressing a subconscious kiss to your head.

“No, you won’t. You wouldn’t let me fail and I won’t let you.” He told you, voice hard with determination.

“Fine, fine. Let the torture begin.” You groaned but shot him a grin.

As the two of you pulled your books out you missed the way Rory and Jess glared at you.

“I can’t keep up, one minute your falling all over Jess whilst you were with the nicest guy ever and now that you’re with Jess you want Dean back.” Lorelai said with an eye roll as she watched Rory.

“What?” Rory jumped, finally looking away from you two. “I don’t want him back, it’s just, I don’t know.” She finished weakly, slumping down in her seat.

“You have to pick, Rory. I told you that when you were dating Dean and you picked Jess.”

“He broke up with me!” Rory protested weakly.

“Because he saw the way you were with Jess, he knew you liked him and no matter how hard that boy tried he knew he couldn’t carry on like that.” Lorelai argued, knowing she was right.

Rory just rolled her eyes before grabbing her bag and walking out of Luke’s. You and Dean were oblivious to the whole thing as you sat close enough together that your foreheads were touching with Dean praising you with every bit of progress you’d made.

-

-

-

It wasn’t long before exam season finally rolled around and you were stressed. Every free moment was spent in either your bedroom, Luke’s diner, the library or Dean’s bedroom studying.

Currently you were on the floor of Dean’s bedroom, books and loose sheets of paper surrounded you. Dean was in the same position on his bed. It wasn’t long before you let out a loud groan, throwing your head back against the bed and rubbing your eyes.

Dean climbed off the bed before sitting next to you. He wrapped his arm around you, pulling you close with concern in his eyes.

“You ok?” He asked softly, frowning as you shook your head whilst mumbling about failing into his shoulder.

“Hey, you’re not going to fail, ok, you know this. Watch,” he said, whilst pulling away from you and searching through your pile of paper before finding a deck of study cards. “Ok, the ratification of the eighteenth amendment led to what?" Dean asked.

“It led to a ban on the manufacturer and sale of the alcoholic beverages.” You said, biting you lip before grinning at Dean’s nod.

“Perfect!” He exclaimed with his own grin, “Which president signed the Antipoverty Act into law?” He questioned, watching as your smile grew.

“Lyndon B Johnson.” You answered confidently, causing him to laugh.

“See you know it!” He told you, “Ok, so if A equals 1,2,3 and B equals 3,4,5, how many sections are in the intersection of A and B?” He asked. You bite your lip as the question ran through your head.

“One?” You questioned and upon seeing him nod you relaxed slightly.

“Good!” He praised and that’s how the next half hour was spent.

“Ok, my turn to question you!” You told him as you reached up for his set of cards.

“Ok, so within a specified period, an increase in atomic number is usually accompanied by what?" Watching as Dean squinted, his head titling slightly to the right in concentration, you couldn’t help but think of how cute he looked. Your eyes widened at the thought, shaking your head just as Dean answered.

‘A decrease in atomic radius and an increase in electronegativity.” He replied nervously.

“Yes!” You beamed up at him and he couldn’t resist smiling back.

The two of you quizzed each other until you feel asleep. You with your head on Dean’s shoulder, Dean with his head resting on yours.

-

-

-

The morning after the two of you had woken up late and quickly rushed to get ready. You had no other clothes and had no time to run home so ended up in yesterdays jeans and one of Dean’s shirts that, whilst tucked in still looked ridiculously big. Though Dean admitted, if only to himself, that he liked the look of you in his clothes.

The pair of you rushed to the school, skipping your morning drinks at Luke’s for the first time since you started ‘dating’. Everyone congregated outside of the hall to sit the first exam of the day; Math.

Dean watched from his position of leaning against the wall as you paced back and forth, muttering different equations to yourself. It wasn’t long before he pulled you into his arms, you relaxing slightly with a second thought.

“You got this.” He told you sincerely, leaning down to kiss your forehead.

“I hope you’re right.” You whispered as you were let into the hall.

“Good luck.” You told him, leaning up on your toes to kiss his cheek.

“You too, Y/N/N.”

- -

-

Two exams down and you were sat outside on a bench waiting for Dean, whilst your math exam was at the same time, he had an English exam that started later than yours.

You sat with your laptop, finishing the last of your college application letters and had them sent off. You’d applied for two ivy league schools just on the off chance you did get accepted, those being Yale and Princeton, though you had also applied to Stanford, NYU, Michigan and Chicago. It was a relief knowing that they were sent off and now all you had to worry about was the exams themselves.

“Hey there.” You leaned your head back to see Dean smiling down at you, looking relaxed for the first time all day.

“Hey! How was the exam?” You asked, knowing how much he was dreading it.

“Honestly, I think it went pretty well but that’s only thanks to all the extra help I’ve been getting.” He grinned at you, leaning forward to peck your lips. “Whatcha doing?” Dean asked leaning his head on yours.

“I just finished sending all my college applications off.” You said letting out a breath of relief.

“I need to send mine off tonight.” He told you as he stood up, holding his hand out for you which you happily took and he led you to the diner.

“Are you working tonight?” You asked him, frowning slightly when he nodded.

“Yeah but Taylor’s letting me go early because I told him I need to study.” The conversation drifted off into talk of the science and lit exams tomorrow before Dean was leaving for work, leaning over and kissing you first.

“What are you doing with him?” Jess asked as he sat himself in the chair Dean had been occupying.

“Excuse me?” You asked, lifting the mug to your mouth. Luke watched from the counter, ready to step in if Jess upset you.

“I mean, Dean, seriously? You could do so much better.” He told you, slouched in the chair like he didn’t care.

“What’s going on there?” Lorelai asked Luke as she approached the counter.

“Dean just left and now Jess is bothering her.” Luke summed up as he poured her a cup of coffee. “Really?” You asked, voice loud enough for everyone in the diner to hear. “You mean like you, the guy who ditched me the moment Rory and Dean split up? Yeah I’m sure Dean’s a real downgrade. I gotta tell you though being with Dean has been so much better than being with you. If you ask me, I think Gilmore’s the one who got the downgrade.” With that you stood, scooping your laptop into your hands and walked out of the diner with your head held high.

It was safe to say your outburst was the talk of the town that evening.

-

-

-

“What a jerk.” Dean replied once you saw him the next day.

“Right.” You said. The two of you were sat on a patch of grass in his garden leaning against one another. One thing that had bothered you from your meeting with Jess yesterday was how you meant every word; being with Dean was so much better. At some point the kisses and hand holding for the public had turned into second nature responses, half the time you forgot you weren’t really dating.

“Anyway it’s fine. Honestly, I was over him a long time ago.” You said causing Dean to smile. “Did you send your applications in?” Dean told you he had and told you which colleges he had decided on, most of them were community colleges but one caught your attention.

“Stanford!” You exclaimed. “You applied for Stanford! Dean, that’s amazing.” You had known Dean had been debating it but eventually decided against it due to him doubting himself despite your protesting and praising. The fact that he had even decided to apply was big.

“Okay, okay, calm down.” He laughed, “I haven’t got in yet. Hell, I doubt I will but it didn’t hurt to apply and-” You cut Dean off with a kiss before pulling back with a grin.

“It’s amazing Dean, they’ll be foolish to turn you down.” You told him, causing him to pull you in for another kiss.

It didn’t occur to either of you that no one was around to see it.

-

-

-

“I got them.” You said into your phone. Currently you were walking to the town centre with six college admission letters in your hand. Dean and you had decided to wait until you both had all your letters until opening them.

“Me too, I’ll meet you under the gazebo.” Dean said before the two of you hung up.

You were so anxious. The fate of your future laid in your hands, literally. By the time you got to the gazebo you were pale and shaking.

“Hey, hey, sit down.” Dean said, taking your free hand and pulling you to sit on the bench. He helped you breath properly before talking to you.

“Whatever happens you’ll be fine, I promise.” He told you. You nodded at him before taking a deep breath.

“Ready?” You asked.

“Ready.” He confirmed.

The first letter came from Princeton, it was a rejection letter. Though you were expecting it, not really wanting the Ivy league ones but applying just to see. It disheartened you but you set it aside.

Dean opened his and saw he was accepted into Southern Connecticut State.

The second letter came from NYU and you grinned once you saw the acceptance.

Dean’s second letter was also an acceptance.

The third and fourth informed you both that you had gotten into the colleges.

You opened the fifth letter and were shocked to find you had been accepted into Yale. Dean grinned at you as you stared in disbelief. Realistically you knew you weren’t picking that college, purely on financial matters alone but also you weren’t an ivy league school person.

Dean and you both had one envelope left; Stanford.

The two of you stared in shock as you read you had both been offered a full ride scholarship.

“Y/N!” Dean exclaimed pulling you up and into a tight hug. Your arms wrapped around him as you took in the words; the college you had most wanted had not only accepted you but given you a full ride.

You were pulled out of your thoughts as you felt Dean kiss you passionately, when he pulled away the two of you were panting as he leaned his forehead against yours.

“Screw this, Y/N.” He said pulling away causing you to frown. “I can’t do this fake dating anymore, somewhere along the way I fell in love with you. Will you be my girlfriend? For real this time?” He asked with a slight laugh, causing you to grin and nod, an exclamation of yes leaving your mouth before Dean pulled you into another kiss.

“I love you too.” You whispered as he pulled back.

Dean just grinned at you before kissing you again, loving that he could now knowing his feelings were reciprocated and it wasn’t just for show.

-

-

The two of you had found an apartment not far from the campus but far enough away that it was still considerably cheap. It wasn’t the greatest place but it was yours and Dean’s home. You took a job in the college library and Dean picked up a job in the cafeteria.

The two of you settled into living together rather well, obviously there were a few arguments here and there but moving out of the small gossiping town of Stars Hollow had done you both the world of good.

Dean was studying engineering at an advanced level and you were finally studying what you wanted and loved it.

The two of you had never been happier and even though it was all thanks to your ex’s and Dean’s fake dating idea, you wouldn’t have changed it for the world.

Click Here For Part Two - I’m So Glad This is Real.

I’m So Glad This is Real. (Part Two)

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Read Part One Here

Requested - Yes - @smokey102​ - Continuation of ‘Why Can’t This Be Real’ taking place during a year in the life.

It had been a long, long, road to get to where you were now but somehow the two of you had done it together. Sure there had been fights, what couple didn’t argue, and there had been a few close calls, though one time you had broke up for a week before realising how foolish the both of you had been.

“Honestly Dean! We’ve been dating since we were seventeen, you really don’t trust me?” You yelled at him from one side of the room.

“Of course I trust you, Y/N!” Dean yelled back, just as frustrated. It was finals week during your first year of Stanford. The stress was higher than ever and you had joined forces with another classmate to study and Dean had read too much into it. Looking back it was the stress of everything building up to this but in the moment it was impossible to think logically. “But you said it yourself, we’ve been together since we were kids! You can’t blame me for thinking you’d want to explore something else.” Hearing those words you glared at Dean.

“Maybe it’s not me who wants to explore.” You said, voice low and cold as you shouldered your way past him. He gently took your wrist in his hand but let go when you pulled away.

“Y/N, you know that’s not what I want or meant. I love you for God sake.” He pleaded as you touched the door handled.

“Don’t call me” You said before walking out the door and crashing at your friends dorm for the week.

After finals you and Dean finally met up, talking and laughing and apologising.

Yeah, you thought, safe to say college was a stressful time.

The two of you visited Stars Hollow during most holidays but during your third year at college the pair of you decided to try hosting Christmas. Clara and Dean’s parents came whereas yours had to travel to see extended family, something you weren’t too worried about missing.

“Dean!” You laughed as you saw the man standing over the burning vegetables. “What did you even do?”

“Stop laughing and help me.” Dean pouted, looking hopelessly down at the broccoli that definitely wasn’t green anymore, nor were the carrots orange.

“Hand it over, sugar. You focus on the mash.” You couldn’t help but laugh again at the weary look Dean gave between you and the potatoes waiting to be mashed. “C’mon, even you can mash some potatoes.”

You restarted the vegetables, missing the loving smile Dean gave you from his corner of the kitchen as he watched you dance around the kitchen with the cheesy Christmas music blaring from the speaker.

He knew then and there he’d be the biggest idiot ever to lose you.

Overtime the two of you had gotten better at hosting parties for different occasions, Dean even eventually learned to cook vegetables without burning them, though the one time he was left in charge of the turkey, well lets just say it’s a good thing you had the foresight to buy a spare.

Graduating from Stanford was something to be proud of in itself. Graduating top of your class was a whole other accomplishment. Dean had hugged you close as he whispered praises and kind words into your hair, kissing you softly and taking you out for one of your favourite dates that you’d ever been on.

Well you definitely thought nothing could beat it at the time but that’s a memory for later.

“I am so proud of you, sweetheart.” Dean whispered as he held you to his chest were you’d sagged out of shock. You were a hard worker but never once did you think you’d be the best in your classes at Stanford!

Dean had told you he was taking you out to the new restaurant that had opened not too far from your home. You were beyond excited as you slipped on one of your nicest outfits.

“You look gorgeous.” Dean said as he came into the bedroom, sliding his arms around your waist.

“Yeah?” You said turning around in his hold, looking him up and down. “Don’t look too bad yourself, sugar.” He grinned down at you before pulling you in for a soft kiss.

“You ready?” He asked and you nodded, kissing him once more before letting him pull you out of the apartment and towards the car.

There was one night you remember clearer than most. You’d been rejected for yet another job, hating the one you were at now but having to persevere until another opportunity came along.

You walked through the door before closing it and just leaning against it, letting your head fall back with a loud thud. Tears that you desperately didn’t want to fall welled up in your eyes as Dean popped his head around the living room door.

“Another rough day?” He asked you, sympathy clear in his eyes.

You just nodded tiredly from where you were. Dean sighed before standing up and walking over to you, taking you into his arms and kissing your forehead softly.

“C’mere baby, I got something that’ll cheer you up.” He told you causing you to look up at him questioningly. His only response was to kiss you before pulling you into the living room, stopping when you paused in the hallway.

The room was covered in blankets and throws, fairy lights were visible from the outside and there was a small opening being held by a pillow in which you could see the TV on with your favourite film ready to play and your favourite comfort food lay waiting for you.

“Dean.” You choked out, a few tears leaving your eyes as you turned to look at him.

“I thought you could use a break.” He told you quietly. You quickly threw yours arms around his neck, standing slightly on your toes to do so. Dean smiled brightly as he rested his head on yours before prompting you into the fort.

You two spent the rest of the night watching each others favourite films again, laughing and smiling the entire time.

It had taken awhile but both you and Dean were finally doing what you loved. You had somehow landed your dream job when you ended up at a party for your old job and accidentally met the boss, wowing him with your knowledge. Dean was working as a mechanic working on vintage cars, it would be a few years but eventually the boss would hand the business over to his best employee.

The best date came after the two of you had moved into a house together, leaving behind the apartment that had become your home and into an actual house. Dean had told you to meet him at the park at six pm, the park was quiet anyway but by then it was practically empty. You dressed appropriately as the autumn chill set in and made your way down to meet Dean.

You gasped as you took in the fairy lights hung from the tress and the picnic basket that Dean was sat next to. Upon hearing your gasp Dean looked up and smiled at you.

“Y/N!” He beamed, standing up and kissing you in greeting.

“Hi baby, what’s this?” You asked as he led you to the blanket. You both sat and Dean started laying food out for the two of you.

“Am I not allowed to take the girl I love out on a date?” He asked sarcastically with a grin.

The two of you laughed. The food was ate but you noticed over the course of the meal Dean had become more nervous. Once you were finished you couldn’t help but ask if everything was alright.

“Yeah, everything’s perfect.” He told you as he wiped his hands on his pants. “It’s just, I love you. We’ve been together for eight years, you’ve been there to help me at Stanford, sat with me when I felt like the world was going to swallow me up and honestly, baby, I can’t imagine the rest of my life without you. I try and it’s just impossible. I love you so much and well I guess what I’m trying to say, or well ask, is will you marry me?”

You were shocked speechless for a moment or two before Dean prompted you to speak. 

Tackling him to the floor from your seated position you let tears of joy roll down your face as you chanted ‘yes.’ You heard Dean laughing, felt his own tears fall down his face before he pulled you back enough to were he could see you.

“Is that a yes that?” He asked, smiling cheekily despite the tears.

“Yes, you idiot.” You laughed, pulling him into a deep kiss.

“Hey Y/N, you ready to leave?” You heard your fiancé call out as he walked into the house.

“Come help me please?” You yelled back at him from upstairs. Dean smiled as he followed the sound of your voice, raising an eyebrow as he saw you sat on top of a suite case trying to zip it shut.

“Y/N, we’re going for a weekend!” Dean laughed as he pulled you up off the suitcase.

“And?” You asked. Kissing him in greeting before looking back towards the case.

“And do you really need all this stuff?” You looked up and saw him glancing at your case and the overnight bag.

“Yes, I do, now are you going to help me shut it or are you going to question me?”

“Both.” He laughed. It took more tries than either of you were bothered to count but eventually the case was closed and the two of you were in Dean’s car and on your way to Stars Hollow.

It was a long drive but finally the two of you pulled up at Dean’s parents house. Greetings were gave but it wasn’t long before everyone retired to bed, the drive exhausting both of you.

You and Dean were cuddled up in his childhood bed, tucked close together whispering quiet words between you and it wasn’t long until you both drifted off to sleep.

-

-

-

Dean had left to go to the store and you had taken the opportunity to go to Luke’s. Memories bombarded you as you walked through the door and you couldn’t help but smile at them all, from agreeing to fake date Dean to arguing with Jess.

“Y/N!” Luke greeted as you walked to the counter.

“Hi Luke.” You smiled and watched his eyes flicker to the ring on your finger that definitely wasn’t there during your last visit.

“So, he finally asked, huh?” Was all Luke said. You never noticed Lorelai sitting a few seats down at the counter looking over in interest.

“He finally asked.” You confirmed, Luke smiling at the love struck look on your face.

“Good, bout time he popped that question. Know any details yet?” He asked sliding your drinks over.

“Thanks. And no, honestly work has been stressful, the last thing I want to do is plan a wedding.” You groaned the smile never leaving your face.

“Yeah, can’t say I blame you.” Luke chuckled before excusing himself to see to another customer.

“Congratulations.” You looked in surprise to see Lorelai smiling softly at you.

“Oh, thank you.” You smiled back.

“Can I see it?” She asked gesturing to the ring and you showed her. The two of you immediately going into how Dean had asked and gushing over it, Luke smiling over at the girl he’d known since she was as tall as his knees.

-

-

-

Dean rounded the corner not paying much attention as he did before he crashed into somebody. He quickly reached out to steady them.

“Oh sorry.” He heard the voice of the girl who he hadn’t seen for years. Since they’d both left for college it was rare for them to be in Stars Hollow at the same time.

“Hey.” He greeted as he took in Rory, the pair hugging as Rory told him how good it was to see him.

“What are you doing in Stars Hollow?” She asked him.

“I’m just visiting my parents for the weekend.” He smiled.

“That’s nice.”

“It’s very nice,” Dean began “we’re actually here because Y/N and I got engaged.” He told her with the same grin he’d always had when talking about you.

“You’re engaged? Dean, congratulations, I’m so happy for you.” She exclaimed, drawing him in for another hug.

“Yeah, thank you.” He laughed.

“How is Y/N?”

“She’s great, she got the job she’s wanted for so long. They’re thinking of promoting her again and yeah, she’s, she’s really amazing.” Dean told her.

“I’m really happy for you, Dean.” The pair smiled at each other for a moment before speaking about the rest of their family, Rory asking about Clara and Dean asking about Lorelai.

“It’s her first love, it’ll probably…” Rory trailed off and the two stood in an awkward silence for less than a moment before Dean spoke.

“Yeah, I know.” Despite the awkwardness he still smiled at her. She was his first love after all and without her who knows where he and Y/N would be now.

“How’re you doing?” Dean asked, not wanting to dwell on the past.

“Me?” She asked, not waiting for an answer, “I’m doing ok.”

“Just ok?” Dean asked, concern in his voice.

“Well things are changing for me at the moment, I’m still trying to figure it out. I’m writing a book.” She announced.

“Well, you’ve read em all so what else you gonna do?” He asked with a chuckle.

“It’s actually about my mom and me and our life.” She nodded at Dean’s questioning response.

“Can I put you in it?” Rory asked. Dean looked confused for a moment, not knowing how to respond.

“Um…” He trailed off and Rory cut in before he could make a decision.

“I mean I’m changing the name to protect the guilty but you’d know it’s you.” She spoke, hoping the man she had once loved would agree.

“Uhm, I uh, I don’t know. What’re you gonna say?” He asked her, not shutting the idea down straight away but not fully loving the idea. Who knows what Rory could write about him.

“That you were the greatest boyfriend alive.” Was the first thing you heard Rory say as you walked into Doose’s with two take out cups, you could see Dean from over the shelves and debated joining them before deciding it was best to just let them talk. She wasn’t wrong about Dean being the greatest boyfriend though, she just hadn’t appreciated it enough at the time, not that you were complaining, you thought looking down at the ring on your finger before pressing your hand to your stomach.

“That you were um, generous and protective and kind and strong and as much as I wish we'd met when I was older and more mature, I know that if I hadn't had you with met when I did I wouldn’t be the person I am today. That you taught me what safe feels like.” Rory’s words were honest and you found yourself relating, safe was wherever Dean was, home was wherever Dean was.

“Ok.” Was Dean’s only response and though you wanted to go to him you knew he needed this.

“And that you had a disturbing obsession with Lord of the Rings-” Boy did you know that all too well, “that you did a terrible Sméagol impression…” Here she was cut off by a laughing Dean, in his defence the impression had gotten slightly better over the years.

“It was not terrible. It was pretty damn good. There were hand gestures.” Like you said, only slightly better.

“I know, I remember. I remember it all really well.” She laughed with him.

“Good luck with the book.” Dean told her softly.

“Thank you.”

“Dean!” She called. “Corn-starch.”

“Pay for it this time.” Dean chuckled before turning away and spotting you. You smiled at him and held a cup in his direction.

“Hey.” He kissed you in greeting and the two of you headed to the gazebo before taking a seat on the steps.

“She’s writing a book?” You confirmed.

“A book.” Dean nodded, playing with the cup in his hands.

“Well she got one thing right. You are the best boyfriend alive.” You laughed, Dean quickly leaning over and kissing you.

“So you want some news?” You asked staring ahead as the two of you stood up.

“News?” Dean asked in confusion. You turned to look at him, smiling nervously and playing with one of his hands.

“You’re gonna be a dad.” It took a few moments for the words to sink in before a grin broke out on the mans face. He took you into his arms and spun you around before placing you down and cupping your face with one hand.

“You’re pregnant?” He asked.

“I’m pregnant.” You confirmed and he pulled you in for a kiss, deepening it quickly. You wrapped you arms around his neck and when the two of you pulled back panting and grinning, you knew this was it, you couldn’t think of any other way you wanted to spend your lives.

No Kissing at the Counter

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Prompts -  Can you do a fluffy Dean Forester x reader?

You let out a sigh as you collapsed into a chair at Luke’s. The entire day had just gone from bad to worse in a matter of hours, starting with your alarm not going off causing you to over sleep and then a fight with your parents that caused you to storm out without the books you needed and then you’d received not one but two surprise tests that would affect your overall grade and you had just known you’d done terrible in. Then at lunch there was the regular high school drama that you had somehow been dragged in to before you could get away to the library and your class just before lunch had announced there would be a group assignment. Those were the worst, you ended up taking control and doing the entire assignment alone and putting the others names on it otherwise you knew without a doubt your grades would plummet.

You were glad to get a few moments alone and sat with your head in your arms for a second before sitting up straight.

“Rough day?” A gruff voice asked.

“Understatement.” You sighed, looking up at Luke who wore a sympathetic look.

“The regular then?” He asked and you nodded, thanking him as he walked away.

Being in Luke’s had always managed to calm you down, the atmosphere of the place worked to soothe your anxiety and troubles and in here with the smell of food, coffee, tea and hot chocolate you could forget about the world beyond those doors.

“On the house.” Luke said, a hint of a smile on his face, as he set your regular drink down and a muffin which you hadn’t ordered. You told him as much.

“Yeah, well, you look like you could use it.” He said before walking off.

“Thank you!” You called to him but he just waved a tea towel in your direction.

You had managed to drink half your drink and eat your muffin in peace before you were interrupted by a tall kid. You recognised him as the new kid from Chicago but couldn’t place his name, though you had heard about how supposedly dreamy he was from most girls in school.

“Um, hi.” He said as he approached your table hesitantly.

“Hi?” You asked, looking up at him.

You could see what all those girls had meant when they called him dreamy. He was the perfect poster boy for a high school crush, tall, fit, probably played sport. The hair looked perfect for running your fingers through and his smile made him look adorable.

“I’m Dean.” He introduced himself, taking a step closer. “I missed class today but I stopped by after school to get the work and Miss Collins told me that we’re partners for an assignment.” You barely held in your sigh, the entire day had been exhausting and now you had to talk about this assignment rather than do what you wanted to do which was sit alone in Luke’s for half an hour more before going home and collapsing in to bed. Instead of doing any of that though, you smiled and gestured to the seat across from you.

“I’m Y/N.” You introduced yourself as he sat down and beamed at you. Even you had to admit it was a pretty smile. “So, I already made a plan up for what we could do but I’m open to suggestions.” You lied. You had spent your break in the library once you finished up in the cafeteria and made a plan for yourself, believing that your group partner would bail on you.

You watched as Dean read over your work, eyes scanning every bit of the page before he looked back up at you.

“This is great.” He told you, “You pick whatever bits you’re happy to do and I’ll take the rest.” Dean told you causing your eyebrows to shoot up. Never in your many years in the education system had someone actually offered to do the work with you, by now you had a reputation of taking over so much so that people wanted to work with you just so they could slack off. “I’m guessing not a lot of people make that offer.” Dean prompted with a laugh.

“The complete opposite actually, they tend to expect me to do the work, which I do because I care about my grades and college is important to me.” You told him, causing him to nod.

The two of you sat together and went over the schedule you had produced, going through who wanted to take each sub topic and dividing the work amongst you. Luke had stopped by to swap out your cold drink for a new one and gave Dean a coffee.

Eventually Dean had to excuse himself as he had work. Your eyes widened as you realised, you’d been sat there for an hour and a half, the schedule long complete and the two of you moving on to talk that was not school related. The two of you had gotten to know each other, you knew he had a sister and why they had moved to small town Stars Hollow, he knew you couldn’t wait to leave and go to college, though you would miss Luke’s. You spoke of your favourite shows, books and music without realising how much time had passed.

“I liked hanging out with you, Y/N.” And the way he said your name made you smile softly in a way you couldn’t recall doing before.

“Me too.” You told him and meant it. It had been a while since you had actually enjoyed spending time with someone your age, finding most of them too immature or too concerned with their image. You liked to be by yourself but something about Dean made you want to spend more time with him.

“Maybe we can meet here tomorrow after school?” He asked shyly, reaching up to brush his hair behind his ear causing your smile to grow.

“Yeah, that’d be good.” You told him, concerned by how true those words were.

The two of you said your goodbyes and you watched as he walked out of Luke’s. Identical smiles playing on both your faces.

“Seriously, that guy?” You jumped when you heard Luke snort from next to you as he began cleaning the cups away and you scooped your papers into your bag.

“What do you mean that guy?” You asked with an eye roll, “There is no that guy, we’re partners on an assignment.” You told him as you stood up, swinging your bag onto your shoulder.

“Whatever you say, kid.” Luke laughed as you left throwing a goodbye over your shoulder.

-

-

-

And so it went with you and Dean meeting each other after school. The meetings went from every other day to finish the assignment, though admittedly that got pushed to the side after an hour of work and the two of you ended up talking about one another, to daily occurrences. The two of you would meet up after school and walk over to Luke’s to enjoy each other’s company. The two of you sat in there for hours and if it wasn’t for Dean’s shift at the market or your shift at Luke’s where you actually had to work and ‘not sit and talk to the pretty boy’ according to Luke, then the two of you would’ve stayed there for the whole night.

At some point you started spending time at Dean’s house and him at yours. The two of you had movie nights and were content to relax in each other’s company, either enjoying the peaceful silence or asking five hundred questions as the movies played, forgotten in the background.

“This is so bad; how do you watch it?” You laughed as you leaned against him. The two of you were laying on his bed as he played some movie you’d long forgotten the name off. All you knew was there were badly edited monsters and a whole lot of goo.

“What are you talking about?” He exclaimed with a grin, “This is a masterpiece!”

“Dean, I can see the microphone in the corner of the screen and I’m pretty sure that’s a stick that is moving the monster in the other corner.” You continued to laugh as he shoved you and grumbled under his breath.

“Fine, fine.” He said, stretching until he grabbed the remote and handed it to you. “You pick something but please God do not put another film like the one you had on the other day.” He begged you with his puppy dog eyes.

“First of all, that was a classic and I’m shocked you’ve never seen it.” You said as you pointed the remote at him causing him to grin. “Secondly, shush.”

You quickly put on a random movie, both of you admitting you hadn’t seen it before. Dean lay down slightly, shifting as he got comfortable, and you didn’t hesitate before laying your head on his chest and cuddling close to him.

“Hey.” He whispered half way through the movie. The two of you were laying fully on the bed now, rather than just reclined, and the room was dark, the only light coming from the tv.

“Hey.” You whispered back, watching as he lifted a hand to your face and felt as he brushed a strand of your hair away.

“Y/N, I really like you.” Dean confessed into the darkness. You could see him biting his lip, his eyes wide as he resembled a puppy, nervously awaiting your response.

You smiled and lifted your hand to rest on the one that was cupping your cheek. You felt him tense and then relax and your hand didn’t push his away.

“I really like you too.” You admitted, butterflies dancing madly in your stomach. You watched as Dean’s face lit up, a smile playing on his lips before he leaned forward. You leaned in too but stopped when he did.

“Can I kiss you?” He asked in a whisper and all you could do was nod before he brought your lips together in a soft kiss.

It was your first, but definitely not the last for that night, kiss. It felt like all the clichés rolled together, fireworks, butterflies, nobody else in the world, all of them described the kiss perfectly.

“Will you please be my girlfriend?” He asked as he played with your hair, bringing you in for another kiss. You managed to breath a ‘yes’ out before he kissed you again and again.

That night the two of you fell asleep with wide smiles and bruised lips.

-

-

-

You and Dean walked into Luke’s the next afternoon just after school had finished hand in hand with matching smiles. As you entered Luke looked between your locked hands and rolled his eyes at both of you as you sat at the counter.

“So, you two finally realised you’ve been dating for months?” Luke asked as he started on your drinks. You rolled your eyes and Dean laughed and wrapped an arm around your shoulders.

“Yeah, I guess we did.” He answered before leaning down to kiss you.

“Hey, no kissing at the counter.” Luke interrupted as he turned around to give you your drinks causing you to laugh against Dean.

“Technically that’s not a rule.” You said pointing to his list of rules with a smirk.

You watched as Luke scowled at you but you could see the hint of happiness behind it.

“I say it’s a rule, it’s a rule.” He told you, pointing a finger at you causing you to raise your hands in surrender.

“No kissing at the counter.” You agreed with a laugh.

You and Dean stayed at the counter for an hour, laughing and talking before Dean had to go to work. Since tomorrow was Saturday the two of you decided it was the perfect time for a first date, though apparently it wasn’t technically the first as you had both been dating for months before realising. Dean told you he’d pick you up tomorrow at 12 before giving you a kiss and leaving.

“No kissing at the counter!” You and Luke shouted at the same time causing Dean to laugh his way out of the door.

You watched as he left with a smile on your face before turning to Luke who was smiling at you.

“I’m happy for you, kid.” He told you honestly.

“Thank you.” You smiled before getting up to get ready for work, already thinking about what Dean had planned for tomorrow.

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.

-

-

-

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.

-

-

-

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.

-

-

-

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.

.

.

.

“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.

.

.

.

“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. 

.

.

.

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.

.

.

.

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.

.

.

.

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.

.

.

.

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. 

Masterlist

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Gilmore Girls Masterlist

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- Why Can't This Be Real? (Part One)

- I'm So Glad This is Real (Part Two)

- No Kissing at the Counter

- Opposite's Attract