#jess mariano headcanon

[bealovesmarauders]

Heyyy! You said you were writing for Gilmore Girls, are you writing for Jess? If so, could you please write headcanons for him or anything you want to write really. If you don’t want it its okay ofc💕

grumpy x sunshine / jess mariano

⋆ ࣪.      ⁺⑅     ⋰˚     *.ﾟ    .˳⁺⁎˚     ˚⁎⁺˳ .    ༺ ˖

jess mariano x reader (headcanons)

wc: 700

a/n: thank you so much for requesting!! yes i do write for jess!! one of my fave bfs other than james potter and gilbert blythe. they’re all so<33  i’m absolutely obsessed with the grumpy x sunshine trope rn and jess with that seems perfect so that’s what im gonna write about if thats ok!!

⋆ ࣪.      ⁺⑅     ⋰˚     *.ﾟ    .˳⁺⁎˚     ˚⁎⁺˳ .    ༺ ˖

jess has always been the bad boy of stars hollow since he moved. that is a fact. and when he meets you it completely throws him off because how can someone be so happy and sweet, and so beautiful at the same time?

obviously he’s not known for being optimistic… so when you meet him while working at luke’s, you try to make it your personal mission to have jess smile at least once a shift

luke thinks it’s great that you two have to work together because jess badly needs a good influence, and you’ve known luke since you were young so you’re completely and entirely trusted with the shop when luke goes fishing and whatever

jess is astounded

and then the way you treat the customers

even kirk likes you- he thinks you’re a wonderful break from whatever the hell luke’s attitude is

you’ve memorized everyone’s regular orders and never fail to serve someone without a smile on your face

at first it kinda pissed jess off tbh because he thinks it’s an act and not genuine

but as he gets to know you better he realizes that you’re just a really lovely sunshiney person no matter what, and hey, maybe you’re rubbing off on him a bit after all

one time he leaves his book at the counter while he’s on a break and you run up to the apartment to give it to him, even though there’s a backlog of customers

“you forgot your book downstairs”

he kind of stares at you, a smile creeping up 

“thanks”

“you’re welcome”

more awkward pauses

“you should really use a bookmark, you know, it’s bad for the pages if you bend them like that”

“you read?”

“yeah. you should really start a new book, though. that one had a super unsatisfying ending”

“oh yeah?”

that’s when everything changes for him

the next shift he comes to work on your day off and you’ve left him a small package beside the coffee machine with his name in cursive on it

it’s a book

your handwriting is inside the front cover with a little note to him

‘for jess, this is my favorite book, don’t bend the pages please :)’

and then there’s a homemade bookmark

from then on you guys start trading books 

and he starts smiling at you more

you guys get closer and more attached, working perfectly in sync at the diner- you’ll have the fries done at the same time he’s grilled a burger, so that everything stays warm for the customers

jess also starts doing more little things for you: wiping down the counter, helping clean up so you can go home earlier, giving you all the tips in the tip jar even though technically he deserves half

until one day you come into work late, eyes rimmed with red, furiously blinking tears away

he’s never seen you like this, so obviously he has to fix it

because you’re y/n l/n. you’re the sunshine of stars hollow

lorelai and rory are there, and so he asks lorelai to help man the coffee 

jess takes you upstairs to his room, away from prying eyes, and asks you what’s wrong, cause he can tell

you just burst into tears

“hey hey hey, you’re okay, what’s wrong?”

cue protective jess.

through the tears you tell him how you’re overwhelmed with school, homework, the pressure to get into a good university, and how you feel like you’re supposed to handle it all by yourself

jess knows it’s not the time for wisecracks

so he wipes away the tears from your cheeks and listens as you talk

when you’ve calmed down, you hug him as a thank you

jess has never really been hugged before. luke and his mom aren’t very affectionate, especially physically

when you finally pull away, his touch lingers

and you kiss him on the cheek very quickly

that’s when jess knows you’re the one

you’ll always be his sunshine, even through both of your worst moments

and he knows he’s going to spend the rest of his life with you, and devote his days to hearing you laugh

but that’s a story for another time

i hope you like this!! thanks so much for requesting, sorry if this got a bit long or if it’s not what you're looking for. likes and reblogs are appreciated! <33

[blueathens]

Idk if I'm doing this right but can you write something with Jess Mariano just being really cute and soft? Submissive isn't the right word but just how you'd think he'd be when he's really comfortable with someone and they're playing with his hair or something.

My Soft Boy

Summary: In which Jess only likes Y/n playing with his hair.

A/N: Okay so I did this as a headcanon instead! I hope you don't mind!

Masterlist//Main Masterlist//Agape Masterlist

It should be known that Jess hates anyone touching his hair

Like no one but him can touch that hair of his

He styles it to perfection

But somewhere down the line, you came along

And it made him rethink it all

Apparently you had been working at Luke's Diner for a long time, and Jess has been surprised he hasn't seen you around in the few weeks he has been there

But then he finds out that you were on holiday

First time he had thoughts about you playing with his hair was before the two of you got together

It was a boring day at the diner

A Tuesday

Hardly any customers

And the two of you (now quite good friends) were playing cards, sat on either side of the counter

And there was a moment where Jess just focuses on your hands

Watching as your fingers fiddle with your own hair

And it brought a weird sensation to Jess and gave him that sudden craving of wanting your hand in his hair

He knew that you knew about his hatred for people touching his hair when you saw one of his dates/hook-ups try touching his hair and him telling her to "get off."

She stormed out the diner and he stormed off upstairs

Stating that he needed to wash his hair now

He came back down with wet hair in his face to continue his shift

And very cautiously you moved to stand in front of him to move a few strands of hair out from his eyes

He didn't tell you to 'get off' like you thought he would

Instead a soft smile appeared on his face and eyes fluttered as the smallest of touches

A few weeks after that, Jess found you reading a book under a tree

He came over to you - completely tired from school (he actually attended because of knowing you would be there)

And without any words he just sat down next to you

And laid his head down on your lap

Guided one of your hands away from your book to his hair

Closed his eyes

And smiled softly when he felt your hand very softly playing with his hair

He never fell asleep so quickly - and he never felt so calm before either with your hand in his hair

He was just falling in love with his best friend - and he knew after today he would have to tell you his feelings

(Especially if he wanted you to continue playing with his hair)

Writing Rule||Character List||Navigation||Masterlist

[youwanttopushmeinthelake]

Headcanon that the reason Jess likes books and reading so much is that, when he was kicked/locked out the house when he was younger, he'd walk to the local library where the attendants would fuss over him and let him read as many books as he wanted before Liz showed up and dragged him back home.

[magewritesstories]

[ ᴊᴇꜱꜱ ᴍᴀʀɪᴀɴᴏ ] ᴍᴏᴛɪᴠᴀᴛɪᴏɴ

summary: Luke doesn’t understand where Jess’s sudden motivation to do well in school is coming from TW: none note: i love him sm, but it’s a pretty short fic

“I’m leaving!”

Luke looked up, astonished at the sight that greeted him. Jess stood in the doorway of the diner, with a book bag slung across his shoulder, headed towards the library.

This had been happening for about two weeks now. Every Wednesday at 15:45 on the dot his nephew— his school despising nephew— had been leaving to go to the Stars Hollow Library

The older brunet had made sure that he was actually going to the library and not off to Walmart to pick up some extra shifts.

Jess made his way across the townsquare towards the local library. Everyone who knew the boy in the slightest would know he had no business there— his habit of annotating books meant he couldn’t borrow any, and he despised the quiet— so why was Jess Mariano going to the Stars Hollow Library?

The answer was very simple; Jess had a crush.

You were always there. Sitting in a faraway corner, of the library, working on homework or reading for an assignment. 

A few weeks ago he’d gathered the courage to walk up to you when you were reading Wuthering Heights. He was surprised when you remembered him from your english and biology classes (mostly because he was rarely there.)

You were sitting in your usual spot when Jess arrived. It was a small wooden desk, with enough place for two people. The edges of the table were worn, just like the fabric of the pillows on the chairs. There was small yellow-light over the table that blinked every now and then.

The black-haired boy made his way over to the table, letting his bag fall onto the floor with a loud thump. 

The sudden sound made you look up from your math assignment, “Oh, Jess, hey,” You gave him a bright smile, “Didn’t think you were gonna make it today.”

“Oh please, I am nothing if not consistent,” He quipped as he tried to ignore the feeling of his heart hammering against his chest.

You rolled your eyes, “They only thing you’re consistent in is bailing, Mariano.” Jess shrugged, “Doesn’t really matter what it’s in, I am consistent.”

“I heard you missed the math quiz yesterday?” You asked, turning back to your homework, “And I missed you in english.”

The teen shrugged, grabbing his books, “I had some stuff to do.” You raised an eyebrow, “Stuff?”

“Yeah, stuff.”

“Well, you missed Ms Bledel handing out our assignment,” You continued. Another thing Jess loved about being around; you didn’t push too hard on things that weren’t your business.

You handed him a copy of your notes, “It’s a two person assignment, and since you weren’t there I made sure we were paired up— so you better not choose next week thursday to be consistent.”

Jess laughed, taking the papers, “I make no promises.”

It was a busy day in the diner when you stormed in. Jess was refilling Rory’s cup of coffee, when the bell rang and you shouted his name.

He looked up in surprise, along with Luke and Rory. “I got an A!” You shouted, running over to him. The black-haired boy wrapped his arms around you in surprise when you jumped towards him, “Thank you!”

You were referring to the fact that he’d helped you with the english assignment and you’d gotten an A for it— which was practically unachievable since Ms Bledel never gave A’s.

Jess rolled his eyes, hoping that the tinge of red on his cheeks wasn’t obvious, “It’s not a big deal,” He shrugged as you pulled away.

“It’s a huge deal,” You countered, “She never gives out A’s, I don’t think I’ve ever gotten an A for english in my life.”

Rory, who was watching the scene amusedly, nodded along, “Yeah, even I haven’t gotten an A in her class before.”

Having heard the commotion Luke walked over to the three teens, “I heard someone got an A?” You nodded, proudly holding up your’s and Jess’s copy of the assignment— bit with a red A on them.

“Oh this is so going on the fridge,” Luke smirked, which made the black-haired boy groan, “Please don’t...”

You giggled slightly at the scene in front of you, before realising you had other places to be. “I have to go,” You said, “But I’ll see you at the library tomorrow?”

That’s when it clicked in Luke’s head; the sudden motivation to do well in school had nothing to do with his threats of kicking Jess out if he failed, it was simple puppy love.

The brunet watched in amusement as his nephew’s eyes followed you all the way to the end of the street.

You had become Jess’s motivation.

word count → 782 words links → gilmore girls masterlist

[munsonsfairy]

nephew with emotionally unavailable parents 🤝 uncle who feels the need to take care of said nephew

[amongemeraldclouds]

✩₊˚.⋆ Welcome to emerald clouds ☾⋆⁺₊✧

Lay on a cloud, it's soft and fluffy. Let's watch the stars sparkle and go on adventures with fictional men in magical realms.

Explore your wildest dreams from cute stories that will have you kicking your feet, to toe curling smut (18+ only), and some angst for when you are in your feels.

Who will you venture with?

Masterlist: ♡ The Slytherin Boys ♡ Lorenzo Berkshire ♡ Mattheo Riddle ♡ Jess Mariano

Starlit notes

✩ Requests are closed ✩ Asks are always open, let’s chat while gazing at the stars and be friends ✩ Spam likes are welcome, you could never be 'too much'

Glittering emeralds

Other links: ✿ About me ✿ Sideblog: @moonlit-witch19 ✿ Tags: 💌 mail | 💚 thoughts | 🌸 games

[scarlet4rose]

Sleepless without you

Jess Mariano x reader

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story: your boyfriend Jess wakes you up in the middle of the night cause he can't fall asleep, he's too busy thinking about you

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It´s 3 am and Jess lies awake in his bed. Every time he closes his eyes, he sees your face before his eyelids. He turns around in bed, but he can't get you out of his mind. Jess sighs, thinking about you all the time without you with him is driving him crazy!

When he dropped you off at your house at 10pm, you said you were super tired, so he didn't want to ask you if he could stay over. So he had decided to go to bed early himself too, but now he couldn't find any sleep no matter what he tried. Dammit! One thing was clear, despite of what he had set out to do he just had to see you!

A few minutes later, he had crept to your house in the dark of night and was now standing in front of your window. He knocks, at first gently, then louder.

"Y/n", he whispers your name and fervently hopes you hear him and have not yet fallen into a deep sleep. After a while he hears noises in your room and you open the window a crack.

"Jess?", your sleepy voice couldn't sound any sweeter to Jess and he starts to grin "Yes, it's me babe, as I live and breathe"

You open the window all the way to let him in and he doesn't let a second pass before he joins you in your room.

"What are you doing here?" you ask confused, "I thought we were both going to bed early?" Jess pulls his left leg through the window and is immediately right in front of you, he puts his hands on your hips and gives you a quick kiss on the cheek. "Change of plans, I guess."

"Oh nooo, Jess, I'm really tired," you sigh.

"Yeah, me too, angel"

"Then why the hell didn't you stay home in bed?"

Jess smiles guiltily and lets out a small chuckle "I couldn't sleep without you. I just... I couldn't help it, I had to come here to see you" Your knees go a little weak and you notice his gaze, which he hasn't yet taken away from you for a mere second.

You sigh again "Alright Jess, then stay, I guess" Jess leans in and kisses you deeply, he pulls away from you and then gives you a second kiss. he really can never get enough of you.

"Thanks, babe, I was hoping you'd say that" he then laughs suppressedly "Without your mercy, I probably would have died of insomnia tonight" you roll your eyes "Oh please! The way I see it, I'm the one now who's gonna die of insomnia tonight instead"

Jess shakes his head as he gently twists your body around so that your back is now pressed against his chest. He slowly walks you back to your bed in the corner of the room. "Nah, no way Y/N. You`re gonna get your sleep, I promise".

Standing in front of the bed, he slowly lowers you onto the mattress and pulls the covers over you before getting in bed himself. He wraps his arms around you and whispers softly "Y/N, angel, I swear I came here just cause I needed to see you. Needed to be with you, alright?" You can't help but smile while you lean back against him "Oh Jess, I guess you`re growing soft. My Jess, my poor Jess..."

Jess frowns slightly "whatever that means. I snuck out and came here to see my girl, that`s not... well- I thought you wanted to get some sleep. You wanna start arguing now?" You grin and turn your head around to kiss your boyfriend on the cheek

"No need to argue, baby, you´re the toughest guy I know, really. well, and...", you can feel his heart beating faster behind you, "and I love you"

Jess presses a kiss on your forehead and hugs you even tighter.

"I love you, too, Y/n"

you snuggel into him and the two of you drift off to sleep.

Good night ˖⁺‧₊˚♡˚₊‧⁺˖

[anxiouspotatorants]

I cannot believe that Lane and Paris would live with the information that Jess worked at a Wallmart and not run over to his place of work at least once a week to terrorize him

[iscahmckrae]

So... how many people here suspect that Gypsy had a secret soft spot for Jess?

[not-with-you-but-of-you]

So,

We all know Jess wears this lovely coat to the infamous dinner with Rory’s grandmother:

But then,

The maid takes it before dinner:

And Jess ends up leaving without it:

And we never see him wear it again…

So the question is:

[emmafallsinlove]

thinking about the hunger games literati!au where lorelai was born in the capitol but ran away to district 12 the minute she realized she’s pregnant with baby!rory and how rory grew up in district 12 without knowing about how the gilmores are respected and loved and how her mom just gave up all of that at 16 without a second thought really when she ran away and how rory saw jess at school but they never spoke with each other very much and how her life are basically perfect - she has a mom who loves her, a boyfriend (dean) and everything according to plan until she gets chosen to the games and with her, jess is being chosen as well and how her perfect life doesn’t seems so perfect anymore because she’s going to die (but also, so does he. she just wishes he’d make it out alive)

[pettydollie]

jess mariano headcanons bc i finally think they’re worthy enough to post

bought your basket omg

he’s like a little kid he loves laser tag it’s so cute 😭

gives you a book filled with annotations of his as a gift

holds your books and your backpack over one shoulder, the other hand holding your hand and walking you to class, leaving you with a kiss on the forehead and lips before wishing you a good class :,)

whenever you get hurt (like a bruise or a cut), he always comes to you like “aww baby, did you get a booboo? its okayyy” like obviously he’s teasing but it’s still cute🤭

always going on drives together

you two get a puppy eventually

nicknames: angel, pretty girl, babe, honey, baby, sweet girl/sweets, sweetheart, snookums (as a joke alr)

when you two walk together, he’s attacking tickling your face in kisses and his hand in your back pocket, arm around your waist, or shoulders

TOTALLY points out when something funny happens in public. like if kirk splits his pants LOL. or even better, if taylor TRIPS AND FALLS (very rare). like he’ll walk by him and purposefully be like “it’s a lovely day today isn’t it sweetheart?” and kiss your cheek ignoring taylor

inside jokes WOWOWOWOW the best i’m telling you. ONE time you couldn’t open the door to luke’s apartment (you were having a very off day) and he would not stop pestering you about it omg. now every time he opens a door, he pretends to forget how to open it just to mess with you

PDA>>>

naps together <33 normally he’s the big spoon but sometimes he’ll be the little spoon. he doesn’t necessarily have to be upset or anything, it’s just a nice change for him every once in a while. and plus, he likes feeling your hands in his hair

insane reflexes!! most of the time when he’s looking at you and you throw something at him, he can catch it. no biggie. sometimes even when he’s turned around just because he knows you so well ;)

you guys trade books allll the time! it’s like a system honestly and sometimes you’ll forget whether a book belonged to you or him first. but if you’re not really into reading, he will definitely try to get you into some good authors!

ugh i’m so in love with him❤️❤️❤️

[saltygilmores]

@frazzledsoul's poll about the worst possible people Rory could choose to babysit her child inspired a headcanon. I need there to be an episode where the teens of Stars Hollow High/ Chilton are assigned Flour Sack babies for a school assignment. if you're not familiar, it was a common trope in 90's and 2000's sitcoms to have a teacher pair students together for an assigment where they'd care for sack of flour or an egg like a child. Mostly you would just have to carry it around with you at all times during school and not break it, there isn't much else you can do with a bag of flour or an egg child. I think you also had to do some written work to go along with it. I went to a weird alternative school and didn't have anything like this so I don't know everything about it. But it was definitely a real thing that happened in high schools, although these days I think they assign more technically advanced dolls that actually cry and record how long you ignore it's crying and all kinds of other stuff. Someone on the sitcom would invetiably drop the egg or split the sack of flour open leading to hilarious hijinks. Anyway -Paris and Rory would naturally be coupled up to care for their FSB, there would be heated and sexually tense debates over which author to name it after -Paris is already charting FSB's future college plans -Madelyn and Louise decorate their FSB with makeup -Dean would be jealous that Rory was giving her FSB more attention than him. -Dean and Jess would be assigned to parent a FSB together because deep down inside I find the idea of Dean and Jess having to grudgingly tolerate each other at school to be rather amusing. -Look, I'm not gonna Jess-Worship here, Dean and Jess would both neglect the hell out of that thing. I want Dean and Jess to fight over who had to carry it around at school before one of them just abandons it under the bleachers at the football field.

-or, hear me out, Jess and Lane. Lane knows Mrs. Kim would be absolutely scandalized if she got word of this project about REPRODUCTION with a BOY so J&L have to hide it from her and make sure the FSB stays in Lane's locker and meet in secret to write their parenting reports, anyway they end up realizing they have more in common than they thought and like a lot of of the same music, and they grow closer and then make out a lot. If you can think of some more FlourSackBaby headcanons please share them

[eminems-skittles]

(3. how they act when they have a crush) with Jess Mariano :)

3. how they act when they have a crush

here you go anons who were so excited for jess content

he’s always hanging around you

if he sees you walking around town, he’ll just jog up to you and start chatting to you about your day

definitely tries to impress you, either with his smarts or over all attitude

likes to take you on little dates

does not keep it a secret that he likes you

memorizes little things

if you offhandedly mention what your favorite flower is he’ll have a bouquet for you the next time he sees you

probably reads your favorite book and annotates it as a gift for you (all i want)

he’s a sweetie <3

[magewritesstories]

[ ɢɪʟᴍᴏʀᴇ ɢɪʀʟꜱ ] ᴅᴀᴛɪɴɢ ʜᴇᴀᴅᴄᴀɴᴏɴꜱ

ᴊᴇꜱꜱ ᴍᴀʀɪᴀɴᴏ — ᴛʜᴇ ʙʟᴀᴄᴋ ᴄᴀᴛ ʙᴏʏꜰʀɪᴇɴᴅ

♠  Jess is the black cat boyfriend no debate

♠  his favourite activities are browsing bookstores in New York to find the most ridiculous books and having movie nights at with home-made pizza

♠  his gifts are usually consist of annotated books and/or CD’s he’s burned for you

♠  so touch starved, like so touch starved, his love language is definitely physical touch

♠  would do just about anything if you just bat your eyelashes at him

ᴘᴀʀɪꜱ ɢᴇʟʟᴇʀ — ᴛʜᴇ ꜰɪᴇʀᴄᴇ ɢɪʀʟꜰʀɪᴇɴᴅ

♦  study dates, study dates, study dates

♦  probably mistook your flirting for picking a fight until Rory told her that you were flirting with her or you just straight up told her you wanted to kiss

♦  loves to do things for you just because, carrying your bags, making you coffee/tea when you working, because you deserve to be pampered, her love language is acts of service no doubt in my mind

♦  when it comes to gift giving it’s usually offhanded like, “Yeah I saw it in the store and bought it, no big deal.”

♦  she’s pretty stubborn so getting her to do things is hard but she ends up doing them because it’s you, and she would do anything for even if she complains 70% of the time

ʟᴏɢᴀɴ ʜᴜɴᴛᴢʙᴇʀɢᴇʀ — ᴛʜᴇ ᴀᴅᴠᴇɴᴛᴜʀᴏᴜꜱ ʙᴏʏꜰʀɪᴇɴᴅ

♣  he takes you to so many places, sometimes it’s places he’s been other times he spotted a new restaurant on his way and he decides to take you there next time the two of you go out.

♣  his favourite thing to do is go shopping for you, particularly enjoys buying you clothes and accessories and then seeing you wear them

♣  Logan’s love language is definitely gif giving, and more often than not the gift are expensive (read: birkin bag.)

♣  whenever he plans dates it’s the out there stuff he thinks you’ll enjoy doing, but he doesn’t mind having dinner at home with a good movie or some music either

♣ he would also do anything for you, even the things you ask him to do halfheartedly or jokingly

ʀᴏʀʏ ɢɪʟᴍᴏʀᴇ — ᴛʜᴇ ᴋɪɴᴅ ɢɪʀʟꜰʀɪᴇɴᴅ

♥  her favourite kinds of dates are the calm ones, like browsing bookstores and going to museums

♥  she loves to sit with you on the couch until ungodly hours just talking about random things or having deep conversations, although the ones about the future are her favourites

♥  love language is words of affirmation, mainly because growing up Lorelai thought her how important communication is in all her relationships

♥   Rory doesn’t really like dates in crowded places, she enjoys the occasional concert or outing to a busy place, but low-key dates will always be superior in her opinion

♥ getting her to do something she doesn’t want to is impossible, she’s very stubborn and when she doesn’t want to do something it’s very hard to convince her to do it

[frazzledsoul]

Hello friend...what do you think Jess Mariano is up to right now?

Not fucking an extraterrestrial pig, that's for sure.

Unfortunately, my 2024 headcanon for Jess Mariano involves him married to Rory and having a handful of kids, so I'm not sure how slutty it is. It also involves Doula getting her GED and either living with or near him and going/planning to go to to some sort of trade school.

However, there are two events I could see him being at tonight: The Fillmore is having a Metal and Beer Fest this weekend with a bunch of hardcore bands playing. It's kind of pricey and I'm not sure he's into that at 40 (or that Rory would want to come along). The kids couldn't go to that, of course. The other thing that's happening is something called the Philly Otaku fest, which is this huge anime/video game festival. I actually think Rory's son (now almost 7) would be all over that and he might need to be there for work reasons. So they'd probably be there at least some point this weekend.