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
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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!!
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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
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“HOLDING HANDS UNDER THE TABLE” prompt with jess mariano please and thank u 🫶
SPOIL
this is the first thing i've ever written for jess, so i you enjoy besties <3 also, i am a lorelei and rory stan, so if you aren't or want to say anything mean, say it to a wall.
"holding hands under the table." (from this prompt list)
when you and jess got together, you wanted to keep it on the dl. well, he wanted to keep it on the dl. although you weren’t best friends with rory gilmore, you were kind of friends and he didn’t want to create any animosity between you, so you decided to not tell anyone about it.
before school, you would meet in the back parking lot where no one ever was. jess brought a surprise pastry to share and a cup of hot chocolate while you brought a new book.
"on the menu today, vanilla scones with lemon icing."
"ooh, luke's getting fancy." you teased.
"i'm pretty sure he bought them."
"then disregard what i said."
"and what book did you bring today?"
"kirk told me i had amazing taste when i bought the book."
"kirk told you that? why would kirk be working at the bookstore?"
"who knows? i've learned to stop questioning kirk." you handed it over to him.
"really?" you shrugged, "i am not reading this."
"oh, you're boring. come on, it's a good book." you insisted. he opened his mouth to argue when the bell rang, "are you actually going to come to class today?"
"i don't know, i kind of like hearing you recite everything back to me." you playfully shoved his head and grabbed your stuff, "i'm kidding. we'll see. i have some stuff to do before."
"what could you possibly be doing right now?"
"stuff." he responded, "i'll see you later. promise i'll be there."
"you better." he leaned down and kissed your forehead before he was on his way, "i'm holding you to it, mariano." he gave you a thumbs up.
true to his word, jess walked into class as if he hadn't missed the majority if the day, "you know, when you said you had some stuff to do, i didn't think it would take all day."
"you'll be happy to know i got you something." he produced a flower he had definitely picked from the garden on the way to school.
"awh, that's sweet." you cooed, "how much do we owe taylor for it?"
"he won't even know it's missing." jess rolled his eyes, leaning back in his chair then grabbing your hand and holding it in his lap under the table, "i got you something else too, but that'll have to wait till later."
"ooh."
"not like that." he rolled his eyes, "a cd."
"cd? jess mariano, you are spoiling me." you smiled.
"anything to see you smile." he gave you a sarcastic smile.
taylor's 2.5k celly!
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