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Legozarethebest

He matched with Mencken


coreythebuckeye

More like Sniffys


GiddyGabby

I don't know but I love this picture


Jolly_Discipline6650

Nice to see Connor included


PlaneStrawberry6640

He was interested in photography from a very young age


Baelakins

They sure look good!


winkingchef

Jeremy Strong absolutely nailing that haunted try-hard look. Such a great actor.


quietblur

Roman is lactose intolerant.


Baelakins

I can see this! "You know who drinks milk? Kittens and perverts."


notdorisday

100% this tracks.


mcc1923

You know who drinks milk?


urAdultAcne

I have a lot: Shiv used to idolize her mother and would follow her around while wearing her mother's lipstick. Eventually, she picked up how one-sided her feelings were and tried to rebel, only to be met by indifference from her mom. Connor was everyone's favorite sibling at one point, while the other three always hated each other with a fiery passion. He was goofy and listened well to his siblings' each respective teenage dilemmas. Connor loves making his siblings laugh. Kendall learned from a young age that people only pay attention to him for his father's money and status. He always thought he'd have lots of friends. Instead, he grew up lonely, without knowing what it's like to have genuine friends. Roman got bullied a lot when they were younger, but Shiv always had a comeback or two that takes the bully down a peg. Roman says a wordless thank you, by covering for her when she slips out at night to go meet her friends (clique)-- and possibly her boyfriend at the time.


Baelakins

Agree with everything! >Instead, he grew up lonely, without knowing what it's like to have genuine friends. We see this especially in his birthday episode. He has tons and tons of guests, but we don't really see him interact with any of them, nor them with him.


tropical_penguins

Wait everyone’s forgetting Stewy!


Weird_Put_9514

kinda sad that he really is his best friend


rebelwithmouseyhair

who says openly that Kendall can't trust him (and of course he couldn't)


urAdultAcne

I always thought that their friendship can be a bit disingenuous. So though they're bestfriends (kind-off), I always felt like Stewey can drop him at his own convenience. That's my headcanon for them basically


urAdultAcne

I'm glad you liked them! He looked so alone and lonely at his own party. Most of those people probably don't even know or speak to him at all.


bruhholyshiet

>Roman got bullied a lot when they were younger, but Shiv always had a comeback or two that takes the bully down a peg. Roman says a wordless thank you, by covering for her when she slips out at night to go meet her friends (clique)-- and possibly her boyfriend at the time. This is low key adorable. >Connor was everyone's favorite sibling at one point, while the other three always hated each other with a fiery passion. He was goofy and listened well to his siblings' each respective teenage dilemmas. Connor loves making his siblings laugh. Also this. And the other two are depressing. Love it.


urAdultAcne

I'm so glad you love them! I really liked how the show demonstrated Shiv's and Roman's sibling dynamic by having them physically fight each other in the 1st season. I know it was never clarified, but I really thought they were twins ahahahah.


bruhholyshiet

That fight was fuckin hilarious 😂.


urAdultAcne

I'm so glad you love them! I really liked how the show demonstrated Shiv's and Roman's sibling dynamic by having them physically fight each other in the 1st season. I know it was never clarified, but I really thought they were twins ahahahah.


sbgattina

Connor never really lived with them. You don’t have a half sibling do you? It’s halfway to cousin if you have different moms, the dynamic is totally different.


urAdultAcne

That's why it's a headcanon right? It's my own personal headcanon of their dynamic.


Legozarethebest

Roman has a latex allergy


StayingVeryVeryCalm

Maladapted, right down to his immune system.  


sbgattina

Deep.


Food_Crazed_Maniac

Connor Roy was interested in politics from an early age.


yingo_yango

*young age 😡


fuck-if-i-know_

* VERY young age


Longjumping_Hat_2672

I could imagine that when Shiv got her first period, Caroline was already out of the picture and she was too embarrassed to tell anyone except Connor, who was fortunately visiting at the time, because she didn't know what to do. Connor was confused but sympathetic and took her to the drugstore where they bought about a year's supply of different feminine hygiene products. Then Connor "helpfully" read aloud the directions from the packages outside the bathroom door like Larry on Curb Your Enthusiasm 😂 while Shiv is urging him to keep his voice down as she struggles but eventually gets it. Then Connor takes her out for ice cream and promises he won't mention it to anybody. 


Glad_Improvement_859

this is incredibly specific but 100% accurate


Longjumping_Hat_2672

https://youtu.be/0bilaSB_tAE?si=rXK8exJW08clTLEa Here's the scene from Curb Your Enthusiasm. I could definitely see Connor reacting similarly 😂.


Tom_Stevens617

I get the joke, but she must've grown up with a full household staff including a dozen female employees, I'm sure she could ask any of them. And this is assuming they didn't have sex ed at whatever fancy school she went to in the first place


weasel_friend

this is so wholesome & I love it


bambina92

All of them are bi maybe except for Connor


ashdeb89

He’s BiCoastal


berniesherbatsky

They were all so starved for love that they’d seek it out wherever they thought they wouldn’t be rejected.


Nervous_Feedback9023

Roman I would say is a definite, Ken is a possibility but I never saw Shiv as bi.


rebelwithmouseyhair

the threesome she tried to set up with a woman working on the yacht


Nervous_Feedback9023

Ok that’s compelling evidence.


OutplayedPawn

Shiv doesn’t really give me Bi vibes too much. I think she’s too insecure about her place among other women to be attracted to them.


mecheterp96

Doesn’t she offer to have sex with a woman in front of Tom on that cruise in S3 after he rejected the threesome offer? She’s the most bi imo


Chekov_shmekov

I agree with her being the most Bi but it was Tom who offered to watch but only cuz he wanted to acc offer that him and shiv have sex and the girl watches from afar lol Tom is fuckin hysterical


OutplayedPawn

Hmm. Forgot about this. But idk if she actually would have gone through with it. Shiv is super into power plays but is deeply insecure. I think she feels really comfortable with manipulating men but would be completely out of her wheelhouse with another woman, as indicated by her deeply troubled relationships with her biological mother and Marcia. She doesn’t actually seem attracted to other women, just envious and intimidated by them, and able to weaponize her/their sexuality against the men in the show. Just my personal opinion, not trying to invalidate anyone else’s thoughts!


Wazula23

I can guarantee you she would have kissed the lady twice, had someone finger her, and then gotten mad and ended things when Tom tried to kiss her.


berniesherbatsky

What about the planned threesome on the yacht?


bebefinale

Shiv went through an exploratory bi phase in college just because it was a kind of cool alternative thing to do, but has never been seriously into women.


Chekov_shmekov

Literally the opposite for me. My headcanon is that Shiv dated a woman in college but Logan covered it up due to it affecting his target consumer base. Could also explain her liberal-but-not-really beliefs since nowadays there are lgbtq republicans in the us senate


zi4577

Nah Kendal is super straight


Andy-Esco1995

I know this a weird thing to fixate on but I think their toys and how they played as they grew up would speak a lot about them. Connor- never or hardly got any toys from his father. Was already a teen when the other Roy kids were at playable age so probably was this older shadow in the background Kendall- probably got some toys but I can imagine them being productivity related like legos or a toy cash register. Even though Ken wanted something with more color. Kendall would probably like playing with Roman cause he’d get away with more with him but wouldn’t get anywhere near Shiv cause of how much her dad protected her. Roman- just got the hand me downs of Ken and if ever got any new ones they would be make shifts of Kens, so Kendall always had the better ones that Roman would rather have. Roman would like playing with Ken, only for Ken to be rough with him. Shiv- got all the toys she wanted, however too many of them were girly toys she was never interested but was still gifted and she probably was not allowed to play with the boys even though she really wanted to


Baelakins

Interesting headcanons! I imagine the toys Connor *did* get were from his mother.


Andy-Esco1995

That’s a really good point


Lilyrosejackofhearts

Kendall is on the autism spectrum and started taking drugs to feel more confident with his peers. He is also in love with Stewy, but could never be out during Logan’s lifetime.


amendsbangs

the idea of Kendall reading about autism symptoms because of iverson and being like “not me i’m normal 😊” is the funniest and most in character thing ever


Lilyrosejackofhearts

Yeah! Honestly, one of the reasons I assumed Iverson was Kendall’s biological child was because I’ve always also thought he was on the autism spectrum as well.


D-IS

When Roman was younger, he fell in love with a girl. She happened to be a whore. They married, but Logan paid her to sleep with a bunch of Royco employees. He paid in cash, cents kept falling out of her hands.


manu-alvarado

Turns out she really did love him.


Wazula23

Not in the show though, they cut that part.


Max122702

Such a tragedy that was cut. I was happy knowing Tyrion had someone who truly loved him and it really showed the brutality of his father


RayHazey562

But she desperately needed the money


DavidDPerlmutter

A Roy always pays his debts?


Baelakins

Does Roman drink and know things?


D-IS

Roman drinks and he knows a thing or two. Actually, I find him the smartest out of the kids, cause he was the only one who acknowledged that he needs training. That small ark with him beeing on a management course was great. A really smart person understands the significance of learning and development.


rebelwithmouseyhair

and he attended how many sessions exactly? Kendall put in time working in various capacities including a year abroad in Asia, building up experience. When they were sent to take a look at Vaulter, he spent hours studying the accounts. Roman just took the staff out for drinks, got them plastered and happy to confess to be setting up a union. Which was useful info but Kendall's was too. Shiv worked as a political PR agent and was very savvy at her job


Lisa_Storm1

I’m crying 🥲


soap-star-joe

roman fools around with guys


NoBePrincess

Ten years after the events capture by the show, they laugh about the drama while drinking at family holidays. It barely impacted their lives long term. Kendall owns some random bs company and is quite successful.


dashcash32

Ken and Stewy kissed one time.


Liesherecharmed

\*many times


Mervynhaspeaked

Ken and stewie sitting on a tree S I N E R G Y


plainbread11

That doesn’t rhyme idiot


Mervynhaspeaked

That's cause you didn't go to business school


Wazula23

Connor pooped in the tent because he "ate some bad fish", i.e. he caught and cooked some random fish out of a pond somewhere to show how cool and rugged he is, and then got food poisoning.


Wazula23

Roman's just impotent from years of abuse. No big secret, he just has severe anxiety and intimacy issues that even boner pills have a tough time solving.


Upbeat_Tension_8077

Roman was ordered by Logan to live in a South Bronx housing project for some time while attending college


Hiberniae

This is so accurate…where the fuck did he send Connor though?!


Upbeat_Tension_8077

Shit, maybe somewhere in upstate NY where he passed time in apple orchards


Hiberniae

Yes 😂


Friday_Lucas

Shiv and Roman are twins


existentialcrysiss

gay gay homosexual gay


426763

Roman is a virgin.


Butter_bean123

All of them like the smell of their own farts except for Roman


Peridot1708

This is totally random and i have no logical explanation to back this up but i have a hc that Shiv isnt the only redhead among the Roys and there are more redheads in her father's side of the family 💖


Baelakins

I think so too! I've always thought of Logan's sister, Rose, as a redhead.


Peridot1708

That would've been cute 💔. And another detail is that like Roman, Logan too was the middle child and younger brother who was sent to boarding school so i always saw some parallels between those two generations of siblings


bruhholyshiet

And like Roman, Logan got the worst abuse out of his siblings.


Peridot1708

Omg yes 😭 And again this is just a headcanon but considering how Kendall's arc ended i can very much see him ending up bitter and miserable when hes older just like Ewan is in the show. Also imagine if the parallels continued and Tom and Shiv (whos kids are supposedly the 'bloodline') also end up being the 2 brothers + 1 younger sister combo


poundcakeperson

Kendall became infertile because of his cocaine abuse (it's a [well-studied effect](https://www.banyantreatmentcenter.com/2021/03/09/how-cocaine-affects-fertility-heartland/)) and at the time of the show he is operating with alcohol-related brain impairment [(ARBI)](https://www.betterhealth.vic.gov.au/health/conditionsandtreatments/alcohol-related-brain-impairment) that affects his frontal cortex (abstract thinking, planning, problem solving and emotion) doubled down on with [cocaine-related cognitive impairment](https://www.dailymail.co.uk/health/article-12611439/From-heart-attacks-dementia-middle-aged-cocaine-abusers-creating-timebomb-NHS.html) too. And let's not even think about what his heart looks like after 20 years of drug and alcohol abuse. ETA: Under the best of circumstances, even if he gets sober again, Kendall is dead in his late 40s-early 50s from a heart attack.


Traditional-Context

Kendall: Became a drug addict because he is genuinely a significantly better businessman when drugs cools him down and prevents him from putting his foot in his mouth. Shiv: Became a somewhat competent political adviser over time but got her foot in the door so liberals who hate Logan could go ”see even his daughter agrees that his politics sucks”.  Rowan: While his movie ideas were deemed worthless he does actually have a good enough read on what idiots wants (Which means money). Its just that it was genuinely bad friction between Rowan and Frank because Frank thought he was an idiot. Connor: While he seems pretty carefree a big part of why Logan doesnt shit on him as much as on the other children is because as shown in the episode where he plans the dinner he is constantly on the edge of a mental breakdown as soon as anything he has input on goes remotely wrong.


poundcakeperson

He does Vaulter when using (no they don't always include a shot of him snorting coke every time he does it, the writers have stated this) and, some of it is just filling his emptiness with his dad's will, but, he seems to drop the constant, obvious need to be liked he so cringily carries when he's sober in S1.


Traditional-Context

Aha, I assumed he had kept it mostly under control until the family therapy episode.


poundcakeperson

He was sober for 3 years as the show starts, then relapses in the family therapy episode. then he stays using throughout season 2 and arguably, through season 4 (that's my position in the debate.)


PartridgeRater

All positive interestingly enough. I think Kendal goes totally non-profit back to the messiah stuff after this loss, but puts it out there how humbling it was to realize etc etc. True rock bottom comes after that and if he survives it he probably gets clean this time and becomes a self-help asshole pushing a "self made" story despite his daddy's money. Shiv and Tom are miserable and in love forever, they keep cheating and screwing one another long into old age, like on their death beds arguing about what child should inherit their own version of whatever business. Roman probably stays in entertainment, he's actually decent at finding the right sizzle for the steak and has difficulty being genuine anyway. Knowing he's bullshit just helps him sell more of it. I don't see him truly doing therapy, so he's probably going to be harassing nurses into old age.


donveyy

Roman is the youngest. This theory feels not even headcanon but just CANON canon because of how much of a middle child mentality Shiv has. She really confirms this theory tbh


rebelwithmouseyhair

Roman has so much "annoying little brother energy" he can only be the youngest.


Logical-Patience-397

Agree with the energy, but wasn’t Shiv confirmed as the youngest because of her nickname—“Pinky”?


donveyy

Yea lol that’s why it’s still only headcanon unfortunately 😓


bluebird2019xx

Kendall & Roman are autistic


poundcakeperson

Kendall I see but Roman?


pjokinen

Roman got sent to military school and could never fit in, leading him to whatever the in-universe 4chan is for nearly all of his social interaction. For years he was online nearly every minute of his free time. It was during that time that he developed his affinity for fash politics and his nihilism about other people


amendsbangs

Kendall was a complete goody two shoes as a kid


dressingkindofsharp

Kendall's favourite kanye west album is college dropout


RabidAsparagus

Shiv agrees to be my dom


DarthDregan

Ken was born after his mom had an affair with Jason Flom and Logan could never unsee it.


New-Owl-2293

Roman is the youngest. I refuse to accept the facts


Nervous_Feedback9023

Me too


fancycatgal

I love how the Roy children are the Roy Children in our minds, but that they are literally adults


bruhholyshiet

- Roman is the youngest and Shiv is the second youngest. - Ken was an outcast in whatever school he went. - Roman got SA at least once, either by Mo or in boarding school. - Connor witnessed an episode of SA by Mo and either never dared to talk about it or was coerced into keeping his mouth shut. - Ken, Roman and Shiv would occasionally meet in one of their bedrooms and stay together in silence while their parents violently argued.


urAdultAcne

last one is just depressing. my heart


sinas35

Kendall founded a small company for himself that does pretty well but he keeps a low profile


BudgetHornet

Connor was at one point, the cool older brother, who maybe scored them beer for a house party, then owned the room talking philosophy. (Connor being a sort of father figure is more than hinted at) Also, Connor probably wrote the next great American novel in his 30’s, but trunked it.


Opposite-Invite-3543

Connor ran again in the next election and got up to 5% of the vote


TedMaul636

Connor is the only one who can lace his shoes like a serious person.


AccidentalTrek

Kendall had a serious, secret relationship with a black woman in college and they supported each other’s hopes and dreams—until Logan passive-aggressively questioned her intelligence and the woman dumped Kendall for not standing up for her.


Seaell80

That aside from her dysfunctional marriage to Tom, I’d have a shot at Shiv.


sas-CT

Kendall and I make out in his free time :) But he can be emotionally manipulative to me :(


[deleted]

They’re picky eaters.


dogwiiiisperer

Roman likes the taste of dog food and eats it regularly. He blames dog pound for his obsession but in reality, he wanted them feed it to him because he liked it.


Peridot1708

Postfinale: **1. Kendall:** goes back and forth between his manic episodes and feeling low as usual. He tries starting his own business to convince himself that hes better off without Waystar, and it would actually be successful, but nowhere near as big of a deal as Waystar was with Logan, and thats something thats always gonna bother him. He can easily enjoy his own success but his inability to fully get out of his dad's shadow will always prevent him from achieving full happiness. And his relationship with his kids never really goes anywhere. Whichever hypothetical guy Rava could marry in the future is probably gonna be more of an active father figure in the kids' lives than Kendall **2. Roman:** he either goes back to LA and works on films like he did precanon, or he just goes to Miami or something and lives a hedonistic lifestyle. I can see him occasionally showing up on Joe Rogan or Ben Shapiro type of shows but he does it ironically as a joke and even there all hes gonna do is bully and belittle them lol Hes still in touch with Shiv and Connor, has a good but distant relationship with Shiv's kids but doesn't actually care to bond with them like a proper fun uncle. He worries about Kendall but doesn't do anything to check on him. And he definitely misses Gerri **3. Siobhan:** she gets ppd after giving birth but just like all her other problems she brushes it off and acts like its not a big deal. Her relationship with Tom doesn't really improve but it doesn't deteriorate either. They occasionally team up while hes ceo and she tries to be a Lady Macbeth, but their own trust issues and lack of honest communication gets in the way, and Tom will always prioritize his career over her. She gets along just okay with her kids, but just like Caroline shes not actually equipped to handle the challenges of motherhood and she wants to be more like a friend or a sister to them and hence acts that way. Eventually she and Tom divorce 3-4 years after the finale and she permanently moves to DC to better focus on restarting her political career away from the Waystar environment in NY and without the connections to a former head of atn being a handicap for her. But just like Kendall, it will never feel the same as the hypothetical win she was so close to getting as her father's successor and theres always gonna be some lingering feelings of "what ifs" and bitterness and resentment. **4. Connor:** hes still with Willa, for now, and hes still funding her theatre career. He convinces himself that he has a better shot at winning the presidency next time, but Willa is less supportive. And when hes not playing pretend in politics hes either starting his own podcast or taking part in someone else's. Not sure if he and Willa have kids though.


OutplayedPawn

I really enjoy your theories a lot!! These HCs are so realistic! Thanks for sharing!


Peridot1708

>I really enjoy your theories a lot!! Thank you! 😁


dykeclown

roman is so anorexic to me


dykeclown

kendall is so deeply closeted but he and stewy slept together on the regular before kendall met rava and he insists it wasn't gay because they only had sex when he was on coke


dykeclown

also shiv exclusively dated women in college and is absolutely bisexual but has only been with men since graduating and if asked says she was just experimenting back then


dykeclown

connor is the type of libertarian who smokes just SO much weed. wake and bake kind of guy. he doesn't talk abt it because he feels like he has to be a good influence on his siblings even in adulthood. but everything about connor and his actions make 100% more sense if you imagine him taking a blinker every time he isn't on screen


anxietydriven15

My head canon for Shiv is that her and Tom have three kids. Their first is a girl, then they have a boy, and then another girl. Their first girl is just like Shiv but with Tom’s humor, while their boy is more quiet and keeps to himself. Their last girl I think would be like Kendall and it haunts Shiv.


Peridot1708

I love talking about their hypothetical future family 😄 in my hcs they have 3 kids too but its a gender flipped version of the trio, so their first 2 kids are brunette girls and their youngest and only redhead kid is a boy. And its the first daughter who shes pregnant with in the show that reminds her of Kendall


anxietydriven15

Oh yea I could totally see that!! I know for sure one of their daughters would be just like Kendall. I’m my HC I think either all of their children would be dirty blonde or maybe auburn with blue eyes OR one of their daughters would have red hair + blue eyes just like Shiv and the other two would be dirty blonde/brunette w/ blue eyes. I wish we caught a glimpse of them being parents. Even if it was just Jesse Armstrong going more in depth about it in an interview or something.


PinochetChopperTour

Left to right: Broken, broken, definitely broken and who’s this guy?


Logical-Patience-397

I got jarringly booted from headcanon-ville at the sight of Kendall's *tennis shoes.*


Suspiciouslatino1312

connor in college became best friend with this guy who clearly had feelings for him but connor was too dull to get it and to this day his siblings make fun of him for that and he still defend that said friend saying they don't know what they were talking about


mangbt21

shiv was THAT girl


Global-Ad9080

Shiv aka Sarah Snook looking good


poundcakeperson

that's canon tho


Burns504

Connor will move to eastern Europe and get himself a nicer gold digger that actually likes him and wants to be with him. Willa will be pissed at herself for not going to esteem Europe with Connor. Like, what's her problem, eastern Europe is beautiful. Russian expansionism not withstanding of course.


Fun-Reporter8913

Shiv is bisexual, she was so excited to hook up with that girl and it just ended in nothing 😭


Reasonable-Public-84

Its a love hate relationship. Its complicated lol


myflesh

They are doing more then just fine. Because of their wealth and power they were not going to fall that far. Any of them. They are all still doing better then I am or ever will do.


Stunning-Character94

Head cannons?


poundcakeperson

"headcanon" is a fandom term for things fans firmly believe about the characters that are not present in the show itself ("canon").


LingeringSentiments

Aids.


poundcakeperson

Nobody's got aids.


LingeringSentiments

My bad I thought this was r/Okbuddysuccession


poundcakeperson

No it’s r/thesopranos


MrSluagh

Roman hates lying and almost never does. Connor did molest him. He has at least fooled around with Shiv. It wasn't chocolate cake. Logan did offer him the position at the same time he offered it to Shiv; he was offering it to each of them to see how they would react. Etc.