Hi love, could i request maybe a Jameson version of your childhood friends to lovers with Grayson. Maybe in Jamie’s version reader is like the daughter of Tobias’ tailor or something like that.
jameson hawthorne childhood friends to lovers head cannons
thankyou so much for the requestsss, this is a longgg one but def one of my favs i’ve written so far
warnings: swearing, use of y/n, kissing, i think that’s it
wc: 4.9k
being the daughter of one of tobias’ close friends, who was also his tailor, meant you were often at the hawthorne house.
when your dad needed someone to watch you when your parents would go out, tobias would always offer for you to come over to the House and play with his grandsons.
at 7, you didn’t have much in common with any of them, but talking to them was still the best part of your day.
one of them in particular made your day better, jameson.
the first time you met him, you were 7 and he was 8. you and your dad were standing outside the front door. a maid opened it, and jameson being the curious child he was, was standing not far behind.
“who are you?” he asks whilst holding a pen, an apple, and a usb stick in his hands. you later learned jameson holding random miscellaneous items was a common occurrence; he practically lived for games.
“i’m y/n”
“hey buddy,” your dad jumps in, crouching to meet jamesons height. jameson already knew your dad and thought of him as a funny uncle he never had. “this is my daughter, i’m gonna be dropping her off with you lot while i’m out running errands, that okay with you?”
“does she like playing games?” he asks
“she loves playing games, right honey?”
“yeah…” you say, looking at your feet. jameson sees that and smiles to himself.
“good,” he says with a wide grin on his face “i love games,” he continues.
“great, you two will have so much fun.” your dad says as he pats his shoulder, “have fun, alright sweetie?”
you and your dad say goodbye, and you’re now standing in the foyer with 8 year old jameson. “hi. what’s your name?” you ask, realizing he hasn’t told you his name yet.
“jameson. do you wanna see my favorite secret passage?”
“you have secret passages?!” you ask, dumbfounded because you thought that stuff only existed in movies.
“so many of them,” he says dragging the “so”. jameson had a slight lisp because he lost one of his top two teeth, and it made you laugh slightly whenever he spoke.
jameson sensed your nervousness at the start and was by your side all day, doing all the talking and getting the awkwardness out of the way.
you swore he was like your white knight in that moment.
in 10 minutes, you were best friends—well, as close as you could get to a random boy you just met. but as kids, all you need is one thing in common in order to be besties for life.
he then introduced you to his brothers.
grayson was standoffish with you at first, but soon enough, he warmed up.
nash was 5 years older than you, so he didn’t really see a reason why he would need to be friends with a 7-year-old, but he was still always polite and never failed to make you laugh.
you and xander got along great; he was like another younger sibling to you.
jameson was just something else. even at 8 years old, he still managed to make little you blush. maybe it was because he was the first one you met; who knows? all you knew was that you absolutely loved talking to him, and you were devastated when your dad came and it was time for you to leave.
“if you want, i can carry your toys outside." he said to you, when you were struggling to pick up all your things and your newfound treasures you and jameson had found in the backyard.(random rocks and stones)
“no it’s okay. i’m a dependent woman,” you say, sticking your chin up high.
jameson grins at you. “isn’t it independent woman?”
“i don’t know... i just heard it on tv” you say with an honest shrug as you both laugh.
ever since that day, you were always over at each other's houses.
jameson brought you so much out of your comfort zone
one day you were talking about how you wanted to have a tea party, but you didn’t want jameson to think it was silly.
“what would you think of a tea party? hypo-hyporectically” you ask, unsure of how to say the word you heard some adults say.
“i don’t really think of tea parties,” he replies, as he’s taking apart a pen, seemingly looking for something.
“but what if you did? like, if someone asked you to one?” you ask again, your voice pitching higher at the end of the question.
“do you want to have a tea party?” he chuckles while raising his eyebrows, looking away from the pen and up at you.
“yeah..? it’s okay if you don’t want to.”
“who said i didn’t want to? i’d love to.”
“oh” you say, and a small smile starts to creep up on your face. “that’s good. we should have one”
“you’re right, let me go call my brothers!" he says halfway through running towards one of the many secret passages.
“wait, no!” you exclaim, and you start to chase after him. “they’re going to think it’s stupid!”
he shouts as he continues to run . “no they won’t, they’ll love it.”
“please please please please don’t ask them, jameson.” you’re practically begging him not to ask them. you were extremely comfortable around jameson, but for some reason, the idea of asking the others to join made you feel silly.
he finally stood and turns around, and he’s extremely out of breath. “fine, only if you beat me in a race.”
“what?! no way!”
“i’ll give you a head start,” he says in a singsong voice.
he stays true to his word and gives you a head start; but he still wins.
looking back, you’re so glad he asked them because they all ended up agreeing, and the whole night was filled with laughter and fun.
it was definitely one of your core memories. grayson was crowned the moodiest tea party princess - there’s a legit certificate of it somewhere in the house signed by all 5 of you.
soon enough, you started to participate in the saturday game mornings, and there was always a friendly fire between you and jameson.
you’d agree to work together, knowing fully well that you’d both end up double-crossing each other at the end.
jameson made a few nicknames for you: the most used one was sewing machine, but it later shortened to “machine”; he said it also worked because ‘your brain worked as fast as a machine’. jameson and his reasoning...
as tweens, you and jameson were a nightmare to adults.
you would always make up the craziest random competitions on the spot:
“who can skip backwards whilst also saying the alphabet backwards without messing up”
“who can close their eyes and win tic-tac-toe 3 times in a row first.” spoiler alert: none of you won that one.
“who can annoy grayson the most today” usually, jameson would win that one.
as you grew older, your dad would ask you to drop off some of tobias’ suits at the house and then come back home.
yes, you would drop off the suits, but you’d spend another 5+ hours there hanging out with jameson.
your dad obviously knew this, but he was fine with it. he knew jameson was a good person, and he had a hunch that you felt something for him.
you and jameson went through all the phases together.
he will never admit it, but he did have a pop music phase for a while with you...
tell anyone, and he’ll deny it like his life depended on it (katy perry, lana, and taylor swift carried him through 2014).
you also had a very short-lived grunge phase. he still has his ears pierced from when you pierced them at home for him.
you both only wore black for a week, but ultimately decided it wasn’t for you.
you also went through a gaming phase. jameson had a whole room built purely for games, which you barely used after that short lived era. it didn’t go to waste though; xander transformed it into his designated robot room.
you guys didn’t go to the same school at this time, so practically every day after school you’d meet up somewhere and talk, or one of you would go to the other's house and hang out there.
you’d usually go to the hawthorne house to talk about your day with jameson, while discovering new secret passages and puzzles in the house.
the thing is, you weren’t like this with anyone else. but when you were with jameson, you never had to pretend or try, being yourself with him was as easy as breathing. you never had to worry about being judged. you always thought this was just because you knew him for so long.
at 14, you had your first real crush (or so you thought).
the guy sat next to you in english, and every time you would need ‘to discuss your answers with the person next to you’ you’d talk to him, and you guys would always go off topic.
talking to him sort of felt like talking to jameson.
whenever you mentioned him to jameson, he would suddenly seem uninterested. you figured it was because the topic of crushes was more girl talk. you soon stopped talking about him.
you two ended up getting into a relationship with him at 15; it was 2 weeks (2 weeks too long) and extremely boring.
he clearly felt the same way, because he’d always be late to your hangouts or have some dummy excuse. one time he blew you off for the mall when you were already there.
you decided to roam around anyway and do some shopping, and there he was, walking hand in hand with some other girl in your school. then he leaned in and kissed her.
you didn’t even know what to do. you froze. it's like your brain was on autopilot, and the only thing it knew how to do was call jameson.
“hey machine, what’s up?”
“hey, um, are you free right now?” you ask, biting your bottom lip and hoping for a good response.
“i’m always free for you. is something wrong?”
“no, nothing's wrong!” your voice begins to waver, and you pray he doesn't notice.
“i know you well enough to not believe that lie. where are you?”
“it doesn’t matter, can i come over? i’m fine, just…” you pause, looking for the right excuse, but you come with nothing.
“just what, y/n?” he says softly.
“i can come over right?” you avoid his question by asking one of your own.
“of course you can,” he says, with a hint of confusion in his voice.
“okay, bye”
“wait wh-“
you shut your phone off and take a deep breath, closing your eyes and pinching your nose bridge. “what am i even doing?” you think to yourself
as you arrive to his house, you notice that some of his friends are just leaving. you start to feel guilty on top of what you’re already feeling as you realize he must’ve gotten them to leave for you to come. it’s like, at any second, you’re going to break and pour out all your emotions.
when he opens the door for you, he immediately does a once-over on your outfit and realizes you were meant to meet up with that guy from your english class. he knows this because whenever you hang out with him, you dress like the type of people he likes. not what you like.
“you wanna tell me what’s going on?” he asks, looking down at you with soft eyes.
you shake your head, looking at your feet, and when you make eye contact with him, the strong facade you put on in front of everyone else cracks, and your eyes start to water.
he pulls you in for a hug and you try your hardest not to cry.
”you don’t have to be strong around me.” the second he said those words it’s like a dam broke out in your eyes.
a few minutes later, no one could even try to stop your ranting. “he’s always- he’s always blowing me off, and whenever he does show up- he’s always so, so, so late” you say in between hiccups and sniffles. you knew future-you would be mortified from the ugly crying on his shoulder, but in the moment, you just needed to be with jameson.
you continue to express your feelings, and when you mention the fact that he was hanging out with another girl today, and kissed her, he pulls back from the hug and places his hands on your shoulders.
“i’m sorry, what?” he says with his eyes narrowed.
“he had you, and he was with someone else? you have to be joking.”
when you don’t respond, he turns his head away from you and mutters under his breath, “im gonna kill this guy”
he turns to face you again.
“what’s his name again? full name”
“jameson.” you warn seriously as you tilt your head.
“his name is jameson too? what a coincidence! we can have a lovely chat about what it’s like to be called jameson.” he remarks sarcastically, with a tight-lipped smile on his face.
you half-roll your eyes and say, "his name isn’t jameson. ive told you his name before”
“i don’t store unnecessary, wasteful information in my brain. it messes with my aura,” he jokes to make you feel better as he moves his hand and gestures around his face, then places it back on his shoulder. “now though, his name is very useful to me. his name?”
you tell him his name, and you can practically see jameson store it away in his brain.
"let's get you inside, yeah?"
the rest of the night, jameson was being extra unpredictable and funny to make you forget about recent events, and he was literally doing anything you asked.
he always complains and groans when you want to watch old timey movies, but that day he had no problem with watching little women & pride and prejudice.
he was still himself though.
“i don’t understand how you like this movie; it’s so... boring.”
“this movie would be so much better with action cars and sound effects.” that one earned a half-chuckle out of you.
“it’s like you don’t even have to guess or predict anything; it just happens?”
midway through his complaining, he looks over at you and sees you're fighting to stay awake.
“oh, that’s why you weren't responding” he murmurs
he told himself off in his brain to stop talking so you could sleep, and at the end of the movie he carried you to one of the many guest rooms and put you in bed.
in the middle of the night you woke up, in an unfamiliar room. you remembered that you were last watching a movie with jameson, ‘did he bring me here?‘ you thought as you got up out of bed and stretched.
jameson heard a knock on his bedroom door and opened it, he was shocked to see you awake.
“what are you doing here?” he says, his voice low like he hasn’t used it in a while.
“um, i woke up, and i couldn’t go back to sleep,” you say as you scratch the back of your neck
“you wanna sleep here?” he asks with his classic jameson smile, even when he’s half asleep.
“if it’s alright with you” you say, starting to smile back at him.
“all yours,” he says as he opens the door fully to let you in first, then closes the door behind you and follows you.
you asked him what time it was, and he answered. but his mind wasn’t focused on the time. it was like every single moment you two had spent together was crashing out of his mind, and all he could think of was you. he laid on his back, staring up at the wall with you next to him, laying on your side, already sleeping.
he knew he loved you. he had known that for a while. he knew you weren’t only a childhood friend, you weren’t only some girl whose dad was friends with his grandfather, you weren’t just a girl who he’d laugh with sometimes. you were it. you were everything to him. you’d seen him through everything he’s been through, and you still always stayed. you were kind and forgiving in times when no one, not even him, deserved it. you were everything and more.
but in his mind, he wasn’t.
“compared to your brothers, your mind is ordinary." the old man’s voice rang through his head.
he looked over at you and realized that he didn’t deserve you. not one bit. he couldn’t bear to see you hurt again, and it would tear him apart if he was the reason for it - because he wasnt good enough. being just friends with you was safer, but it was also tearing him apart every passing day.
he needed to be better, for you.
over the next few weeks, jameson started to distance himself.
you were so confused. “did i do something?” “was the crying too much?” “i messed everything up” were thoughts that clouded your brain for months.
jameson on the other hand, was thinking this was all for the better.
“i’ll get better at this, i'll be perfect for her, and then ill come back”
he just kept striving to do one more thing, but it was never enough for him. he felt like he’d always be one step away from perfect.
but he had to be perfect, so he kept trying.
you and jameson turned into strangers who happened to know everything about each other. you’d still text each other sometimes, pretending like nothing happened and wishing the other a happy birthday.
your birthdays didn’t feel the same without him.
your favorite birthday was when he gifted you a riddle box you had to solve when you were 14. once you solved it, there was a letter inside titled “to my best friend." some spelling mistakes here and there, but you still treasured it like it was worth all the money in the world.
it was the summer before you started 11th grade, and you were going to be attending heights country day that year.
you went downstairs to get a cup of water, and as you were standing looking at the fridge, you noticed an old drawing you made at eight of you and your family hung up on the fridge. on it, there was little jameson next to you and labeled it “my best friend”.
your mood was instantly dampened, and you started reminiscing about times long gone.
you went to reread the letter in the riddle box that he once gave you. you knew that moving schools would mean you’d have to face jameson much more frequently.
you wanted to remember what you once had. “maybe if i don’t mess up this time, i could have that again.” it was putting salt on an open wound.
you sat down on your desk, placed your water next to you, and opened that riddle box once again. the familiarity of the whole process from how many times you’ve opened it made it no longer a riddle. it was practically muscle memory now. you took out the letter, and reached to turn on your lamp, accidentally knocking the cup of water in the process.
you immediately got up from your chair as the water spilled all over your desk and picked up the letter.
“shit shit shit shit,” you repeated as you tried to salvage it.
“no no no, this can’t be happening,” you murmured as your voice started to shake.
you brang it up in front of your face and noticed the back, and you started to see writing appear that you'd never seen before.
“am i tripping?” you questioned, and turned it around back and forth, then you started to chuckle. “there’s no way.”
you then realized he used one of many hawthorne classics - invisible ink.
you sat down back at your desk and took a picture of the letter, just in case it disintegrated later on.
you started to read through the new writing that you had just discovered.
“hey machine, i know you’ll never read this, but i’m writing it anyway. that’s something i do a lot—things that are useless just for that rush of excitement, for that risk. mother says im “hungry”. im starting to think she’s right.
in all seriousness though, i'm actually not hungry. i just did a scone eating competition with xander. not our brightest idea. i think i wont have to eat for the next 10 years of my life.
okay, in actual all seriousness, i love you. i should’ve probably done some big lead up to that, but honestly, thats all i know. all i know is that i love you. you make me feel a feeling that’s unexc unexpli unexplainable—that’s love, isn’t it? whenever i’m with you, i never feel like i need more, like im "hungry." you’re it for me. you’re everything and more. the old man once said to me, “there’s men like us only love once, fully, wholeheartedly. it’s all consuming and eternal." i think he knows—hell, he probably knew before i did—that i love you. how could i not? everything about you is so perfect. i knew you were going to be someone important in my life since the second i laid eyes on you. i just never knew how much.” your hand covered your mouth as you continued to read, as you got to the end, you swear your heart broke in two. “…what i'm trying to say is, i would carry your toys for you any day if it means i get to see you smile - if it means you’re happy. i would go through any phase in the world, as long as it's with you. i would discover every secret passage if it meant discovering it with you. i'd climb every mountain, i'd watch every rom-com, i'd read every book, i'd do anything, if it was you asking.
i love you, machine.
endlessly and eternally yours,
jameson”
by the end of the letter, you were in shambles.
he loved you? for all this time? and you never even knew? if he loved you, why’d he leave?
you knew the letter was old, and it was written before you two drifted apart, but something inside of you was itching to call him and tell him what you found—what you know now.
you called him, waited, and waited. you were just about to hang up and forget all about it when he picked up on the 5th ring.
“jameson, hi”
“machine?” he sounded almost in shock. he cleared his throat and spoke again.
“y/n, hi. to what do i owe the pleasure of this call?” he seems to have regained his composure quickly.
a smile found your face. he still talks the same.
however, it quickly fades when you remember the premise of which you’re calling.
“i know this is extremely random, but um. i was rereading a letter you once gave me, the one from that riddle box.” you pause and wait for his response.
“yes?”
''and water spilled on it." you continue
“oh.” you hear him shuffle for a second, and he continues, “i’m sure you enjoyed 15-year-old me’s spelling mistakes."
“there weren’t that many, actually,” you say with a small chuckle.
jameson hated talking to you like this, like you weren’t practically the same person split into two. but he knew it was his fault.
“yeah, i'm pretty sure i used a grammar checker. or i asked grayson. same thing”
you laugh. and your laugh has him regretting every single decision he made that didn’t involve you. he was such an idiot for leaving in the first place. he needed to make things right.
“that’s grayson for you,” you reply, and he’s brought back to reality.
he lets out laugh, and then says, “you know, i heard from a little birdie that you’re moving to heights country day this year.”
“yeah, i am actually,” you reply with a small smile.
jameson hears your smile in your voice. the things he would do to be able to see that smile.
the rest of the conversation goes smoothly, and it ends with jameson asking you to come over for a rundown of what to do in school. what he was really asking, was for you to come over so you could talk about the letter.
you arrived at the hawthorne house exactly on time.
jameson opened the door and smiled at you. in that moment, you swear you actually felt your heart skip a beat.
a few hours later, when you’ve gotten back into the rhythm of talking with jameson and laughing with him, he actually started to help you with school. he gave you some of his books from last year for you to catch up on.
he was on a ladder, reaching for one of the books in one of many libraries, and you were behind him basically ogling at his arm and back muscles that were peeking through his white shirt. he really had grown.
he suddenly says “my feelings didn’t change, you know.”
“what?”
“the letter.” he says when he turns around with the book in his hand. he pauses for a second, searches your face, and continues.
“i feel every single thing for you now than i did then, probably even more if it’s even possible. i could never forget about you. every corner of this house has memories of me and you. so does every corner of my mind. i love you.”
he puts the book down, takes a step forward, and you look up at him.
“jameson i..” you trail off, trying to find the right words. i’ve loved you since i could remember. every good memory i have has you right next to it. since the second i went through that first passage with you, i had a feeling that i never felt before, and it kept growing with every step i took. every step we took, together. i love you." and after a second, you continue. "but why’d you leave?” you say that with your eyebrows slightly furrowed and a light shake of your head.
when you say those last words, a flash of hurt passes through his eyes.
“i’m sorry. i wish i could give you some great reason why i did, but i cant." he takes a deep breath in "i wanted to be better for you. i didn’t want to be ordinary with you.” that was the first time he ever confided in someone about that feeling. ordinary.
“jameson. you’re everything to me.”
“i wasn’t enough.”
“you’re more than enough” you tell him truthfully, and you reach your hand up to his face.
he does the same, and somehow he steps forward to be even closer to you than he already is.
"i love you, jameson, more than anything in this world. i'll spend every day of my life proving it to you if that's what it takes for you to see that you're not ordinary, you could never be. you're everything."
he looks down at you for a few seconds, and his eyes flicker from your lips to your eyes.
he murmurs in a low voice, “if i kiss you, i don’t think ill ever be able to stop.”
“who says i want you to stop?” your voice comes out barely audible.
and with that, he kisses you.
it was a slow, passionate kiss. one that said all the words you two weren’t able to. it wasn’t rushed; it was love.
your arms moved to wrap around the back of his neck, and his moved to your waist, drawing you in somehow closer than you already were.
for the rest of the night everything was normal between you two, like no time had passed at all. except you were extremely giddy, and jameson had his flirt on 100x more.
later on, you two are lying on the couch with your head on his chest. he was playing with your hair when he broke the comfortable silence.
“you know that one guy, from your english class?”
“ugh, don't remind me of him,” you groan.
jameson chuckles, and you feel the vibrations coming from his chest.
“i’m sorry, i’m going to have to,” he says through a smile as he pats your arm, and he resumes.
"whatever," you grumble through a small smile. "continue?" you add on.
“after you left that day, i told grayson what happened—not everything, but enough. he was the only person at the time who knew i liked you. back to the point, we went to the mall, and lucky for us, that guy was still there. his little lady friend seemed to be somewhere else. but there he was.”
“oh my god,” you mumble as you turn your head to face him, “what did you do?”
a smirk starts to appear on his face as he looks down at you. “what makes you think i did anything?”
“well for one, that smirk on your face,” you say with a laugh, “and secondly, well, i know you.”
he looks up at the ceiling and smiles.
“me and grayson had bruised knuckles for a week or two, but it was worth it.” he chuckles as looks down at you.
“oh my god,” you mutter for the second time that day as you turn your head to the side and look away from him. you look back at him with raised eyebrows and a finger pointed at his face, “you’re insane.”
“you love it.”
after a beat of silence you respond, looking into his eyes with your voice barely audible.
“yeah, i guess i do.”
this was so longg, honestly idek if these even classify as head cannons anymore. atp they’re whole stories.
sometimes writing for jameson is hard for me because i have no idea how to think like him, so i apologize if this is out of character 😭
anywayy i hope you enjoyed, lmk if you did! 🤍
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