Roman Roy Headcanon - Blog Posts

Succession Preference: Handmade Presents From S/O

Requested: Preference: How the Siblings react to their S.O giving them a handmade gift? (maybe a bouquet of flowers they thoughtfully picked out at a florist themselves, baked goods, a coffee/tea mug they decorated or a homemade meal?) i hope this sounds good!! ♡ - anon

A/N: This is so cute my love!!!! Thank you for requesting!!! I really hope you like it!!! Feedback is always appreciated!!! 💜💜💜

Connor appreciates your home cooked meals to no end. He thanks you forever. It doesn't matter if it took hours or thirty minutes, Connor won't let you live it down. He brags to his siblings all the time about how thoughtful and caring and considerate you are. You try to shrug it off like it's nothing, but he won't have that. Seriously. The only time he ever got anything home cooked was when he was a little kid, maybe once a year if his mother made him eggs or a grilled cheese. You go above and beyond when you cook. You never mind, you love sharing it with him. He compliments everything, making you laugh. Food is how you show your love. Sometimes, when you have the time, you make extra and send it with him to give to his brothers and sister. They love it, too. It's like they've never eaten before. They're all full of compliments and it makes them like you even more, which doesn't hurt either.

Kendall loves when you bake anything, but especially when you bake something he loves. You've been doing this since you were dating, but now that you're married it's become a rare occurrence. With work and life you don't always have the time. When you do, you like to send him to the office with everyone's favorites. Logan's blueberry muffins, Gerri's lemon squares, Karl's cinnamon rolls. You make extras of Kendall's favorites so he can have them at home and at work, surprising him when he gets home and the Tupperware is empty. It makes him feel so loved, so appreciated. He's a menace in the kitchen, always wanting to taste the raw batter and lick the icing. When you do it, it means you really thought about him, what he likes, what makes him happy. Not many people have done that in his life. But you? You make time for him and his happiness and that is priceless. It reminds him that he is capable of being loved.

Shiv isn't sure what to say. It's perfect. A bouquet of all her favorite flowers and colors in a vase she didn't even know either of you owned. Next to it is a little card with her name wishing her a good day. It sits on her office desk, just waiting for her. No one had ever done anything like this for her. Not her family, not Tom. She wasn't even sure he knew any one of her favorite flowers, and yet you had them all. You didn't sign the card, but you didn't have to. Tears well up in her eyes, but she's quick to blink them away. It's beautiful. She doesn't want to touch it or move it out of fear that petals might fall off. Once word spreads that you got specialized flowers sent to the office, the jokes start flowing in. She doesn't care what anyone has to say about this, especially her father and brothers. She feels so loved and seen, the most she's ever felt in her life. When she gets home she talks lightly of it, thanking you, but you can see the smile she's trying to hide. This small act means the world to her.

Roman is shocked. He doesn't know what to say. You start to feel insecure, like this wasn't something he'd like let along love. Under the ribbon and wrapping paper is a handmade mug with the date you officially became a couple. It was a little misshapen, but other than that it was perfect. You'd picked out the perfect color palette, too. All his favorite colors. No one had ever done anything like this for him before. No one has ever thought about him so thoughtfully. Roman holds out his hands, careful, scared he's going to break it. He looks it over a few times and holds it close before realizing who he's supposed to be. This fucking thing, it's, it's- thank you. That's the last thing he says about it. You catch him using it almost every day, holding it with both hands, hand washing it. He truly loves it. So much. It's his most prized possession. He never says anything about it again, though you catch him going through every cupboard looking for it, mumbling to himself. It's right in front of you, Rome. He breathes a huge sigh of relief. If he lost it or broke it he's not sure what he'd do.

Random Headcanons About Baby Roy:

Warning/s: addiction, addiction mention, drugs, alcohol mention

A/N: I think about Baby Roy all the time, lol. I just love them. I thought some fun headcanons would be nice :) Based on these headcanons and this fic series!

Baby loves screamo. Anything and everything screamo. Also any alternative artist! The more raunchy, the better. Any car or room they're in, they're listening to it or humming it or playing it in their headphones. Everyone's come to expect it and ignore it as best they can. Especially Karl and Frank, they hate it. Gerri just shrugs. it's not hurting you or anyone else, leave it be

It absolutely drives Connor insane, especially when you and Roman gang up on him and recite verses. Roman doesn't love your music, but it's so worth it to watch your other siblings cringe and get all uncomfortable

"That d*ick tastes like yankee candl-" I love Ashnikko lol

"Y/n, please."

"You wanna hear a so-"

"No."

Baby unironically plays Where's My Juul?? by Lil Mariko in front of Connor who has no idea what a juul actually is lol

Baby has a wicked sweet tooth. Kendall's been sneaking them candy since they were little, but it seems like you always have something sweet. A lollipop, gumballs, gummy bears, etc.

"You'll get a cavity."

"This is my one vice, let me be."

Shiv is always holding out her hand for whatever you've got. She doesn't ask, she just expects it. You never mind, it's nice to share with her. Besides, it makes her feel like a little kid, too

Baby loves gory movies. Growing up, when all the kids were together, they'd have movie night. When it was your turn, you always chose the goriest thing you could find. Rome would sit with his hands over his eyes and Connor would hold a pillow, But you, Ken, and Shiv would be totally into it

"Just wait! His head gets ripped off!"

"This can't be appropriate."

Baby is actually very smart. Despite all the partying, their grades were perfect. Logan had no need to worry. Maybe you weren't showing up to class, but you were there for tests and that's all that mattered. You throw your intelligence in your brothers faces

"Can you even spell egotistical?"

You make endless jokes about your sobriety that none of them like except for Roman. The others shoot daggers at you with a look that says "not funny" You think it's funny though, and that's all that matters

"I'll be at the bar, you guys chat. Kidding! I was kidding, jeez."

"Does anyone else need a strong drink right about now?"

"They say the food is like crack, but I know crack and this isn't that."

"I used to take handfuls of pills to this song. Now look at me, I've become a monster."

Connor is horrified. Every time you say anything, he's speechless. Shiv gets very serious and Kendall spirals, but Rome likes it. If you can't joke about it, what good is it?

Baby has lots of tattoos and piercings. It's the only socially acceptable way to self harm that isn't drugs and alcohol. Logan hates them and Connor thinks they're unsightly, but you don't really care. Gerri always wants to see the new ones you got, though she prefers they be covered up in the office

"I like that one, that one's very cute."

"Thanks, Mommy."

She hates when you call her that. For you, your and Gerri's relationship, it's not at all sexual like it is with Roman. She is genuinely your mother figure. She is warm and caring and only wants the best from you. She can always tell when things are getting bad again

"Oh honey, you don't look so good."

"Mommy, I don't feel so good."

She really does love you. Someone has to. She knows your mother and Logan don't. Someone has to be there for you

Both Karl and Frank are afraid of you. Between the music, the addictions, the tattoos, the piercings, everything is intimidating to them. You're not competing like your siblings, that scares them the most. You want nothing to do with the company

"Think they're rabid?"

"Might be."

You love it, the way they always back away when you get too close, like you're demonic or infected

Baby, I think, would write a lot. Not just your feelings, which are so hard to put into words, but good things that happened, reasons to stay sober

You have a notebook or something that they use to write in. You've brought it to every rehab you've ever been to and constantly reread it over and over. No one knows about it, and if they notice, they don't bring it up. It's yours

Reasons To Stay Sober: Connor, Kendall, Shiv, Rome. Connor, Kendall, Shiv, Rome. Connor, Kendall, Shiv, Rome. Connor, Kendall, Shiv. . .

You have a sobriety birthday and every month you bake a cake. It always turns out shitty, lopsided, and burned and runny at the same time, but decorating it makes you feel like a kid again

You're always wearing your siblings clothes. You're always stealing someone's jacket or socks or shirt or sweater. You like it. It makes you feel close to them

They've just come to expect it

"You look better in that shirt than I do, keep it."

"I was going to anyways."

You have those moments of deep regret and embarrassment and self-consciousness that always end up in tears, but your siblings are there to pick up the pieces

Connor especially will just hold you as long as you need and listen to everything you have to get out

You feel so deeply sorry for hurting them and scaring them so much. You just wanted it to stop. You wanted not to he angry anymore

They tell you they understand, but you know they don't. Not really. They can't unless they've felt the way you have

Baby falls asleep on all the siblings. Even Roman will let them get away with it, but no one else. You snuggle into them and have the best sleep of your life

"Quit moving."

"Don't use me as a pillow, then."

You get away with (mostly) everything because you're their baby and they love you so much. They love you so much it's gross

Connor still prides himself on the way he raised you. There were bumps in the road, but you ended up perfect. Absolutely perfect

They all pride themselves on how they raised you. It wasn't always good, they weren't always there, but they're making up for all that now. Logan is gone. Slowly they're breaking the cycle, for you and for them

Things will get better. You've hit rock bottom so many times and always found a way out. This is that. This is your out

Being Roman's Favorite Sibling Would Include:

Requested: I looooved the "being connor's favourite sibling" headcanons and I was wondering if you could do some for bwing roman's favourite sibling as well? :) xoxo - anon

A/N: He is so baby boy. He is so little man. How much I love little man. Lol anyways!!! I hope you like it my love!!! Thank you for requesting!!! Feedback is always appreciated 💜💜💜

Being Connor's Favorite Sibling Would Include:

Roman didn't like that you were born. There were enough of you running around, he didn't need another sibling. Especially not one as young as you considering he was almost a teenager by the time you were born

Still, there's not much he could do. Like the rest of your siblings, he looks after you. He starts to like you when you're about six months old. That's when you start to look and act like a little person and not, in his words, some gross little flesh monster

You immediately love him from the start. Roman is your everything. He's the one you want when you cry. He's the one you want to sit next to. To play with. To follow around and copy. He secretly loves when you'd take his sunglasses and a pair of his shoes and walk around your little toddler walk pretending to be him

"I'm you, Romey."

"You're not as cool as me."

From a young age you call him Romey. Everything is Romey. Even when you're upset or fighting or anything, he will always be Romey

He likes you now that you can walk and talk and go to school. When your other siblings can't, he'll walk you home from school

"Guess what I learned today?"

"Brain surgery."

"Noooooo Romey, I learned how to multiply."

"That's helpful too, I guess."

All you wanna do is hang out with him, be his little shadow

You know that your father is not a good man. When you fall off your bike and get hurt you don't run to Logan, you never have, instead you go to Roman. He's not very sympathetic, but he'll sit you on the counter and clean you up

"I want the dinosaur bandaid."

"You can't always get what you want."

He gives it to you always, not wanting you to be upset

You're the only one who can go near him after Logan's hit him or berated him. He tends to self-isolate and pushes everyone away. Only you can open the door and come inside and wrap your arms around him. He doesn't push you off, he can't. That would be like acting like your father. He lets you stay as long as he needs and when he's done, he tells you he's okay. Somehow you always know when he's telling the truth and when he's lying

"I'm sorry about Daddy."

He makes it very clear if Logan ever touches you like that you go to him. Not Connor, not Kendall or Shiv, him. He has this terrible feeling that Logan can't differentiate between you two, that he sees you as an extension of Roman instead of your own little person

The older you get the closer you become. You pick up on his sarcasm, his wit, and annoy your siblings to no end when you gang up on them

"Kendall's gone crazy."

"He's been crazy for a while, you're just noticing?"

"Can you guys please stop talking about me?"

"You're forgetting I grew up with him."

As a joke, and maybe not as a joke, he has you in his phone as Mini Me. Mini for short. He'll call you on the phone and text you and you're always Mini

"Mini, where's Shiv?"

"How should I know?"

"Mini get out, the adults are talking."

"I'm an adult!"

"Not with that attitude."

You guys tend to stick together. Roman was right after all. Logan goes after you like he does with Rome. You're a teenager the first time you show him what's been going on since he left the house. Your eye is bruised and swollen shut. You try to put ice on it and get rid of the swelling, but it's too late. When he sees you, he loses his cool. You have to hold him back from going to your fathers study

"Please don't go after him."

"Y/n-"

"Please. It'll only make things worse. You lnow this."

"Fine. Fine, okay? Fine."

From then on you have more sleepovers at his apartment. He makes up a bed on the couch and you stay up and watch movies with snacks

"Isn't it past your bedtime?"

"Do I look five years old?"

"Four and a half."

"Fuck off."

Your first word was a swear courtesy of Roman. It was most likely fuck, but he swears he can't remember. It was the best day of his life listening to you say fuck over and over again, giggling in that little baby voice. He tries to play it off like he doesn't care abut really, it'll be etched into his memory forever

"Are you sure you're okay?"

"I'm fine, Romey. Dad does it all the time."

It makes him feel sick knowing you were going through all that and he wasn't there to protect you. You protected him and you're the baby sibling. It's his job to look after you, to protect you

You guys fight all the time. Not in a mean way or a serious way, more like calling ewchother stupid and dumb and pushing and shoving. You never go too far, you never do anything to hurt one another, just as a means of disagreement

"You're so fucking stupid."

"Me? Are you kidding?"

"See! Can't even tell when I'm being serious."

"You're never serious, Romey."

Whatever you accomplish, he's always quietly cheering you on. He's not going to be as outwardly affectionate as Connor is. It's just not in his nature. When you get your degrees and find your place at Waystar he visits your desk multiple times a day

"Look at you becoming a corporate pig."

"I learned from the best."

You and Roman actively make fun of Tom and Greg

"Did you see what Tom was wearing?"

"Fashion disaster, I know."

"Why is Shiv even with him?"

"Daddy issues. Mommy, too."

You stick up for Roman when your siblings make fun of his lack of dating/sex life. It's none of anyone's business

When you do start to date and bring people home and find that someone special, they know they have to get through Roman for things to be serious

"Where'd you find this one? A back alley?"

"Please be nice, I really like them."

"Are you paying them? Are they paying you?"

Say what he will, he's happy you're happy. It hurts watching you grow up. You were his Mini Me not so long ago. Now you're taking part in the company and finding love and you've got your own place. You showed everyone that despite being the baby of the family, you're a force to he reckon with

He loves you. He loves you more than he loves himself. He doesn't say it, and when he does it never comes put right, but you're his baby. You always be

Succession Preference: Baby Introducing Their First Date

Requested: 2nd preference: how would each sibling react to their baby sibling (reader) introduceing their first date (gn neutral if possible) - anon

A/N: This is just too cute to imagine!!! I love it!!! I hope you like it my love!!! Feedback is always appreciated!!! 💜💜💜

Connor is so excited to meet them. Unfortunately for you, the whole family is over for dinner and insists on meeting your date before you go out. You were hoping to sneak out after drinks, but before dinner. Connor won't let you get away with that, though. He's eager to meet them. Really. Unlike the rest of your siblings, Connor fears no ill intentions. He truly wants to see the best in people, even the people trying to date his baby sibling. When they get there, they're immediately taken into the living room. You have no time to warn them at all. He doesn't intend for it to be an interrogation, but Connor asks them a lot of questions. Are they in school, what do they do for work, do they have any siblings, pets, what is their family like, what are their intentions with you, etc. This is just a first date. You like them, you want things to go well, but this is definitely not the type of deal where they should be meeting your family. This is not going well, not if they're with Connor the whole night. Your date just smiles and nods along. When your brother is satisfied, he winks at you before you go, telling you "they're a keeper". You thank him, getting the hell out of there before he asks anything else.

Kendall doesn't like this at all. He goes to your father, asking if he's heard about this little date you've got planned for tonight. Of course he does. Why would Kendall care? No, no he has to put a stop to this. He thinks his father has lost his edge. He tries to bribe you with money and alcohol and shares in the company for you not to go. You try to remind him that you're an actual, legal adult. That you can see whoever you want when you want and he can't stop you. You also remind him that this is a first date, it could be nothing special. It definitely won't end in marriage. You don't know that, he warns. What are you talking about, Ken? You were never this way with Shiv and Rome. He wants to tell you it's because you're his baby. Shiv would date whoever she wanted and didn't care what anyone thought. Roman rarely dated and when he did it was never that serious. But you? You're his baby. He watched you grow up. He can't let you go that easily. He just can't. He doesn't care if this person is some supernatural genius or the next president or the bringer or world peace, he will not let you go with them. You're just a baby, his baby.

Shiv accidentally and not so accidentally crashes your date while you're on it. You and your date go to a very local, very popular cafe that just so happens to be near Waystar. You didn't even think about if you would run into your family, you just picked it because it was a nice place. Shiv spots you laughing and smiling across from someone who most definitely is not a friend, at least not a friend she's ever seen. Hey kid, she says, dragging a chair over with her. Who's this? Wanna introduce me? If you could crawl under the table and hide, you would. Instead now you have to sit and smile as your sister quite literally interrogates them. What do they want with you, what are their intentions, do they respect that no is a complete sentence, do they know who your father is, etc. You want to die. They have this look in their eyes that screams help me, but you can't do anything. Every time you try to get her to go away and move on, she blatantly ignores the hints. When she's done, you swear it's taken forever, she leaves with her coffee and a wicked grin. Your sister doesn't like anyone wanting to date you. As far as she's concerned, you're too good for them. You'll always be too good for them. All of them.

Roman doesn't like them at all. He doesn't even give them a chance. He makes fun of them, he points out their flaws, he picks on them. They come up to meet Logan just for a second before you go to dinner. You don't know that Roman is there until you come out of the bathroom and see your date being taunted by him. Immediately you defend them, hissing at your brother to stop it. You send them down to the lobby, needing to talk to your brother. What the fuck are you doing? You ask, ready to kill him. He was going to scare them off forever. You really liked them, you wanted things to go well. Them? You like them? Are they paying you? That earns a slap to his arm. What is wrong with you? He laughs. How much time do you have? You just roll your eyes. You'll have a big fight about it after, but for now you have to go downstairs because your date is waiting for you. Roman would never put this into words, but you dating means you're all grown up. He doesn't like that thought very much. What happened to the baby he used to rock to sleep and the toddler he held on his shoulders? Suddenly you wanted a partner? Nope, not on his watch.

Succession Preference: Youngest Sibling Fainting

Requested: I would love either a preference of how each succession character would react to there S/O fainting around them or a baby roy sibling fic were she faints around some of their siblings ❤️Thank you ❤️❤️ - anon

A/N: I combined some of the ideas, I hope you don't mind!! I love this so much it's not even funny like they would all freak out internally I love it. I wanted to show different reasons for the fainting from each sibling, so that's why I chose the preference btw! I hope you like it my love! Feedback is always appreciated 💜💜💜

Connor is so worried. You're sitting outside his ranch when you go pale. It's been pretty hot out, but today takes the cake. You excuse yourself, getting up to go to the bathroom, when you faint. Immediately he's calling out for Willa, his heart going into his stomach. He loves you more than life itself. He's scared beyond belief. You wake up to the two of them above you, each of them using a tone they'd use to hush a crying baby. What happened? What the hell were they doing? Slowly, they get you up, walking you inside, getting you water and an ice pack for your head. You're burning up. Connor can't help but apologize over and over again. Of course it's not his fault, of course, but he won't hear it. It was the sun you tell him, but he's not listening. It's his job as big brother to take care of you, to make sure you're okay. When you're not, and he doesn't notice, that's on him. Connor banishes you to the inside for the rest of your stay, asking you every fifteen minutes if you feel okay, etc. He won't have you fainting again, not on his watch.

Kendall had no idea what happened. It was a side effect of a medication you were taking and telling no one about. Ever since your father passed you hadn't been able to sleep. Every time you closed your eyes, you saw him, his body. You'd been on the plane, you'd been there through it all. You were dizzy, but only a little. You thought you could manage, that you were fine. You pull up in the car outside of Waystar, getting out, when you faint. Kendall runs around the car, calling your name, trying to shake you awake. You're only out for a minute, but it feels like an eternity. You're groggy, scared, unsure of what happened. He gets security to get you some water, holding on to you despite your fighting. You scare him so much he's gone pale. He doesn't stop asking if you're okay until you're seated in the office, someone checking you out, shining a light in your eyes. That's when you tell him about the pills, the not sleeping. He had no idea, though he knows he should have. He's your big brother, he should be protecting you from everything. He should have been there for you, before this. He makes a vow to himself that he'll be better, he has to be.

Shiv knew something was off. Ever since you'd been officially hired by your father at Waystar, you haven't been eating or sleeping or really leaving the office. You'd been tasked with a minefield and every wrong step would cost you your job. You were in the middle of presenting to your father, in front of everyone: Logan, Shiv, Gerri, Karl, Frank, Hugo, Kerry. You lose track of what you're saying in the middle of the sentence, so unlike yourself. That's when the dizziness hits, when you clutch the desk, when you drop. You bang your head pretty hard on the floor, though there isn't any outside damage. Shiv steps up right away, getting to the floor. Everyone is calling your name, questioning what to do, she's the only one who works. She fans you with her hand, calling your name. You're awake before you know it, terribly embarrassed, apologizing to your father. She doesn't let you get up though, not right away. She doesn't care how much work you have or what your father thinks, you hit your head pretty hard, she's surprised it's not cracked open. She needs to take care of you now, cursing herself she hadn't noticed earlier, hadn't stepped in and intervened earlier. You definitely feared losing your job now.

Roman had no idea how to help. You'd been there with him, before the funeral. Unlike his overly enthusiastic demeanor, you couldn't stop from freaking out. You were hyperventilating, feeling sick to your stomach, calling to him from the bathroom doorway that you didn't think you could go. That's when you faint, from getting all worked up. He drops his cards, running towards you. You look dead. Roman is shaking you, yelling your name, about to be sick himself when you open your eyes. He breathes the biggest sigh of relief, doing something so unlike himself: he hugs you. Hard. You have no memory of falling, of the last few minutes. He makes you stay there so he can call someone, anyone, unsure of what to do. Shiv gives him instructions. Through it all he cracks a few jokes, his heart still racing. You scared the shit out of him. He gets you water and gets you up slowly, bringing you to the couch. Shiv and Ken both on their way, coming to check on you, already in the same car. Awkwardly, he pats your leg, threatening to never scare him like that ever again.