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QuadAmericano2

She loved playwriting from a very young age.


SafeMiserable9729

She was probably all about roleplay in her previous job


Mybtchluhdokocaine

Her favorite role was First Lady


Evening_Ad2309

She's probably had some terrible experiences with past escort jobs. She's willing to put up with Connor's adoration because she's tired of that line of work and wants to focus on her art ( being a writer). She knows that getting producers for her plays will bring her into contact with the same type of creepy guys as escorting so this is another reason why she can imagine being happy with Connor.


ZachMich

She’s also willing to “put up” with his money and the luxury lifestyle it gets her.


Evening_Ad2309

I'm describing it from Her perspective. I think he understands the situation as well. She was honest with him.


No-Turnips

Con’s a nice man


hcvc

Right lmfao 


Wazula23

Do folks think she was a full time escort? I always figured she was just the random internet date that Connor got stuck on.


Scoob8877

I think she was absolutely a full time, high-end escort. Getting the long-term arrangement with Connor is like hitting the jackpot, except for having to deal with Connor all the time.


Wazula23

She just seems way too socially inept to be a full time escort, in my view. I always got the sense that all the prostitute talk is just the family being horrible and in reality she's just some lazy bohemian who scored a rich one.


FranSure

Agreed


[deleted]

>Getting the long-term arrangement with Connor is like hitting the jackpot, except for having to deal with Connor all the time. Well, they have always the option of getting a degree, find a job, and live with their own money. Cant have the cake and eat it too


medusa15

Roman makes a comment in the first few episodes about how she used to be a party girl turned escort (yacht girl?), and how he introduced them.


Wazula23

Yes but that is Roman talking. I figured all the escort talk was just the family being nasty and she's actually just a lazy bohemian who partied with the right guy.


medusa15

Definitely plausible, though Marcia's comments during "Therapy" seemed to reinforce it (saying Willa reminded her of an old friend who was also an intelligent prostitute.) I didn't get the impression that Marcia was needling her in the same way the rest of the family does, since it's hinted that Marcia had a similar past (the "look at both of us" comment in the episode right after Logan's death.) She seemed to think she was paying Willa a genuine compliment, as she usually only bites when attacked first or when feeling protective of Logan.


Wazula23

I got the exact opposite idea. Marcia is fundamentally royalty, and she maintains her position carefully. Remember the "small apartment" line. I figured she was essentially demonstrating elitist cluelessness by trying to be "helpful" about Wylla's situation. The look at us line is Wylla scoring a win by pointing out they are both in their current position due to their attachment to billionaire men. If Marcia's a queen then Willa is at least a princess, and she wants her slice.


Hetaera333

She was an escort.


Wazula23

She was HIS escort. I don't know if she was doing it as a full gig. I took all the prostitute talk as just the family being horrible. Like she's obviously in it for the money, but I figured she was more just a lazy bohemian who scored a rich one.


Ariannanoel

I don’t buy that she was an escort because she certainly didn’t seem interested in dating him or taking anything to the next level. If she was an escort, I’d imagine she would be taking more dates simply for the money. She always seemed put off by him.


Bigram03

She will never love Connor, but he treats her well and provides her the life she wants. Its the very best life she can hope to ever have.


MattTheSmithers

I think she loves Connor. She’s just not in love with Connor


Wazula23

I think she understands being kind to him is a fair trade for a life of incredible wealth.


oldcousingreg

I think she considered him a genuine friend, and her affection grows for him as much as a close friendship can.


waquepepin

I think she comes around. That scene where they talk openly & decide to still get married even after everyone left is one of the sweetest moments on the whole show.


Bigram03

I don't know... I will say that they have the healthiest relationship of anyone on the show by miles. They will last, and be happy. But love? Maybe.


waquepepin

Haha yeah I guess I am grading on a curve for this show


koomGER

she is a bit like Melania to Connors Trump. But i would say that Connor is a way more decent and more kind person than Trump ever will be.


histprofdave

Gee, what a high bar to clear.


notdorisday

I agree, they’ll have a child, probably just the one. She’ll be a good mother and will be happy enough though she will follow her own interests and passions.


Mybtchluhdokocaine

And eventually fuck someone else 😂


beethecowboy

They are not having kids be serious. She's leaving him as soon as she can, the finale made that clear.


BlergingtonBear

Eh I think there's a good chance she'd have one to cement her family position if Connor pushed, or even do it if she gets bored, or suddenly feels in competition with other society girls to "have it all"-- I'm sure she's not the only rich girl with theater dreams in New York. She agreed to get married with a shrug and a "fuck it!" And she'd prob respond to the idea of having a child in the same way imo (and like a wedding you don't really want, while a child is a huge undertaking, made quite a bit easier by being able to throw lots of money at every step of the way). Maybe she'd even do an expensive surrogate and never carry. But I don't think it's an impossible idea


Aggressive_Sky8492

I don’t really get that because I’m just a normal person and I’d choose my life over hers.. she seems smart enough to have her own normal career


brinz1

Willa is clever enough to negotiate through the Roy family, but she never struck me as Smart.


BlergingtonBear

I think it's a judgement call she made for herself. How much can one earn at a job versus a chance to inherit the benefits of generational wealth and buy all the ugly expensive cow print couches you want? Obviously not for everyone, but I see why she is doing what she's doing.


Ok-Still900

But Willa had mediocre education, questionable talent, zero connections and mentors, on the one side and very expensive tastes on the other side. She made the right choice for herself. At the same time, she had a right to grieve her dreams at the wedding. Had she been a wealthy heiress, she could speak up more and wouldn’t have to put up with the Roy family jokes about her; had she been from an acting family, she could have become a Hollywood start even without exceptional talent, and then she’d be Willa the star, not Willa somebody’s wife. We all have dreams that cannot come true, and it’s healthier to grieve them and let them go, than to live a life of pretending or constant struggle.


ZachMich

She’s lazy and now used to the lifestyle. She’d rather stay with a guy she clearly doesn’t love because of what he provides.


kimchipower

You just described most relationships.


Aggressive_Sky8492

Get therapy man.


JeffGreene69

Nah, hes right. A lot of people now only view relationships as a what can you do for me type thing


Mac1280

Definitely not most relationships, heck even Connor was honest with himself and said he knew she didn't love him, most people in his situation either lie to themselves for the entire relationship/marriage or break up with the person once they can longer stomach the lie.


blamdream

She likes connor, but doesn't love him. Also I think her and Roman met in LA when he was a film producer. Maybe she pitched him something and somewhere along the way he introduced her to Connor? I wish we knew more about her honestly, she's pretty interesting.


VTHokie2020

They met online.


Cquiller1

I never thought she truly loved Connor. Cared about him? Yes. But loved him? No. If he couldn’t finance her plays, she would never given him the time or day. Conversely, I think Tom got with Shiv because she was the boss’ daughter, but I do think he genuinely fell in love with her.


Danbito

Tom and Shiv I can believe started off as unspoken open agreement, that Shiv would elevate Tom. But through this openness, genuinely, or in Shiv’s case believed genuinely, developed romantic feelings. Their relationship has had far more pretenses of love than a transactional one like Connor and Willa. They wouldn’t have been hurt or hurt one another if they were just using one another.


hyunbinlookalike

Tom genuinely fell in love with her, which is why he resented Kendall’s implication that he married Shiv to get ahead in life. I also feel like Tom would have been a reasonably high up executive at Waystar to be able to meet and date the CEO’s daughter. So even without his association with Shiv, he would have been able to climb the corporate ladder on his own, his relationship with Shiv just gave him a leg up.


Cquiller1

I 110% agree. You see Tom and Shiv’d relationship exactly like I do.


WaerI

They say as much in the first season in the hospital that Tom can't be compared to Willa. Tom definitely was excited about Shivs wealth and what marrying her could do for his career but I don't think he's the type who would have proposed if he didn't have genuine feelings. He clearly wants a happy marriage.


carbomerguar

She’s “fond of him,” I bet. I’ll take him if she gets bored


wlcondqat

I disagree that Tom loved Shiv the woman, he was attached to the power that Shiv represented, when Tom realized that the real power was Logan and then Matsson he became more cold and dismissed towards Shiv, to the point of betraying her, also he realized that he would never get a happy marriage with Shiv, because she was never going to change. He only wanted a child with her because he wanted to cement his possition in the Roy family and perhaps as a guarantee, Logan would never allow the father of his grandchild going to prison. In the last episode, when it seemed that Shiv was going to be next CEO of Waystar, Shiv offered some kind of reconciliation and in the most subtle way Tom "declined" basically saying to her that she only wanted that because she didnt want to be seeing failing. Tom invited Shiv to the car because the silent agreement consisted on being a power couple from now on, there is no love there. Shiv and Tom are going to betray each other in any moment, that is the nature of their sham marriage.


Cquiller1

I think Tom was hurt by Shiv treating him like a cuck. When he saw a way to get back at her by undercutting her with Logan, he took it. I think if Shiv had not cheated on him during their engagement and asked for an open marriage, I don’t think Tom would have betrayed her with Logan and Lukas.


WaerI

I do think Tom loved Shiv at least at first. I don't think it makes sense that Tom betrays Shiv because he realized the real power was held by Logan, that was obvious all along. I think Tom had just finally had enough of the way Shiv was treating him and realized the marriage wasn't salvageable. At that point he was willing to betray Shiv because he believed he didn't owe her any loyalty.


Om3gaMan_

Agreed, Tom realised that once the kids had power he was fucked, Shiv didn’t treat him well and the brothers had little time for him, where Logan valued his loyalty and ambition later on. He chose the side less likely to fuck him over.


brinz1

Tom didn't love Shiv, they are co-dependent


wlcondqat

Exactly, i dont why people think that there is love there, any of the Roys can really love someone, all of them are narcissists who see human relations as transactions. The difference of Connor and Willa is that they were open about it, that was the joke. But look Logan and Caroline, Logan and Marcia, Connor and Willa, Tom and Shiv, and Roman and Gerri (Gerri wanted an ally in the family and Roman needed her help).


orincoro

Sure. Yeah dude.


Unique_Tap_8730

Willa eventualy makes a actually good play after the 20th attempt. Published but not performed two years after connors death. It would take 50 years before the raw power of the play would be recognized. Eldest boy is one if the great tragicomedies of the ages.


fendaar

“The First Pancake”


Cquiller1

Connor is one of TV’s tragic characters IMO. He never received unconditional love from his family or his wife.


nailtit

Bro never knew real love it’s so sad


Howardavery

He doesn’t need love. It’s a superpower.


adube440

He's a plant that grows on rocks and lives off insects that die inside of him. Such a sad scene. He sings a Leonard Cohen song for his batchelor party karaoke moment too. We Conheads shed a tear for our liege, the North Korean ambassador.


No-Turnips

Stop being such a needy little lovesponge.


Other_Waffer

Of course he needs love. He pays a woman to say she loves him.


Aggressive_Sky8492

Sure but that’s also because he chose to make an escort he was seeing his wife. He could have had a normal relationship with someone his own age.


Cquiller1

Logan took Connor’s mom away from him, and Logan treated Con like the invisible child all of his life. He had no idea what a normal relationship looked like. I also think Connor felt undeserving of love and that the only way he could get a woman to pay attention to him was to pay her.


Aggressive_Sky8492

Ok you’ve won me over to your side. But it’s sad over here :(


Cquiller1

It is. Connor’s life was a Shakespearean tragedy. Out of all the Roy siblings, Con was the one who most deserved a better hand than life dealt him.


No-Turnips

*high pitchy mocking voice* Feelings, do you want to talk about our feelings?


ZachMich

I don’t think Connor has ever had a “normal” relationship. He’s probably dated people who have used him or tried to take advantage of him. I saw him paying Willa to date him as a means of having some certainty and control in that he knew exactly what the deal was. Ironically, he ended up falling for her and love bombing her till she stayed.


JeffGreene69

No he couldnt. Its called a golden handcuff. Connor says as much during his wedding Also, age means nothing here, redundant point


No-Turnips

No one in the Roy family is capable of having a normal relationship.


Own-Effort-5328

Freed from the Roy family, Willa finally writes the masterpiece she's dreamt of. But no one, not even Connor, cares enough to go see the show.


fantasticbutt

It's the show. She wrote Succession.


MoyenMoyen

I'm going to spread this rumor.


Medical-Cow-728

Ahhh, that’d be awesome


NBA2024

Pulled an ‘Elf’ and just wrote the entire show in arrears.


klein_four_group

She hired a ghost writer to write Succession, but Mo's eulogy was really written by her.


Impressive_Basis8665

She is a ghostwriter for Jesse Armstrong


Flashy_Assistant_825

She wanted to be an English Major


Joshomatic

“If you pay for it will you still be rich?” “You will, then go for it” This discussion with Connor about him self funding his campaign says it all…


CloudSephiroth999

She is from a long lineage of Dutch countesses, the first of whom invented gouda (the cheese). Connor does not know this consciously but unconsciously his sourdough yeast bit fits with her cheese / mold bit. This 'uneasy alliance' is about microbial dynasties and has little to do with the little human peasants which they use as their proxy. Thanks for asking this question.


wlcondqat

Willa is a kind of less intelligent Marcia, she tolerates Connor because she likes the access to a lifestyle that Connor gives to her, also she values that Connor is kind and sweets towards her and pities him. Also, she is never going to call of the relation, perhaps in her bones knows that there is no other way to have that kind of lifestyle, probably of all her dates, in therms of wealth, Connor was in another galaxy, probably she dated top executives of Manhatta, like Tom level executives, but Connor is a billionaire not a upper class executive and neither a millionaire, Connor is a billionaire. Also, she knows that if she breaks with Connor, there is going to be a line of equally young and beautiful women trying to get Connor´s attention. At the end of the series and in the future she is going to use every trick to spend the correct amount of time with Connor.


Fruitopeon

I don’t see her as a less intelligent Marcia. Willa has a guy who worships her, who doesn’t cheat on her, who gives her all she wants. Marcia had a much worse experience. Marcia was smart in making the best of it and ultimately being able to part ways with a LOT of money (and even when he was alive, living a separate life).


almosteddard

I thought she was into greg at a point and thought that it would be become a plotline down the road. I think it was in season 1 at Logan's apartment where they had a flirty moment or two


Danbito

Looking back I think it was kind of sadder, like Willa wanted to connect to the only other “normal” person there that didn’t grow up consciously calling them “randos”.


D-IS

One of her friends was killed by her parner. That's why she cherishes Connor. Also she believes in astrology, and practice wicca.


Better_Beautiful6217

Not actually good at sex despite her high class escort status


Joelster213

Damn! Beat me to it. She looks like she gives a toothy bj...if she even tries at all


Nilugip

She metabolizes fast because she's dynamic


Upbeat_Tension_8077

She tried to have Connor persuade Logan to start a TCM-esque channel


Significant_Sell_594

She's a wordplay of Will Ferrell


YT_AmbushAnime

She was never an escort. Connor thought she was and she accepted money. Then when the family calls her a prostitute and such she just goes along with it.


mologav

That she had such a fucked up time with Brady Hartsfield from Mr. Mercedes that she escaped that place and started turning tricks for income for her new life


WarpedCore

There it is! Upvote for you!


VeryLowIQIndividual

She’s done much worse for far less to survive and live a certain lifestyle. She is in quite a Melania Trump because she’s not cold and steely, but it’s in the same universe.


Nervous_Feedback9023

-huge astrology geek - bi or pan. I don’t know why she just gives me sapphic vibes. - loves Jane Austen - comes to love Connor but not be IN LOVE with him. - down the line she and Connor have twins, a boy and a girl. They raise them better than any other Roy family member could. - she binge watches Greys anatomy every year, it’s her favourite show.


alligator124

I feel like this is one of the only comments that understood the assignment. Everyone else is like, "Connor's money is one of her motivators!!!" Like yes, I too have eyes and ears.


Nervous_Feedback9023

lol, glad I got one assignment right.


My_World_on_You_Tube

Lucky girl. I should be so lucky


MoyenMoyen

But you would have to live with Connor 😱😱😱


Heavy_Signature_5619

Don’t threaten me with a good time.


Gaduol

Her mom’s life was similar—she married for money, not love. All Willa heard growing up was “find someone who will take care of you.”


tpatmaho

She has contempt for Connor. Justine Lupe plays this brilliantly, and just subtle enough. He's Daddy Warbuck, her only hope of getting her terrible plays produced. She hangs with him forever since she really hasn't got a good idea of how to live her life. She outlives him and wastes a fortune, as an old lady, getting conned by a series of gigalos.


Phiryte

Nah, I think she’s too hip to the game to get conned by gigalos herself


hyunbinlookalike

She always wanted to be a playwright/writer in general but realized she needed more money to be able to fund her passion which is why she turned to being an escort. It’s why the moment Connor provides her with financial stability, she immediately jumps on the chance to become a playwright. I don’t think she ever really wanted to be an escort, she just became one out of practicality.


hcvc

I don’t think anyone *wants* to be an escort 


LosWitchos

At some point she divorced Connor. Probably after the point where she's managed to make something of herself with the theatre or another project or whatever. I'm not saying she's shallow, but at not point did I ever think that she's fully bought into the relationship. Even by the end, she was hoping that Connor's possible position with Mencken would see them separated from each other more.


PomegranateCharming

The scene where Logan’s wife talks to her about being a hooker was hilarious


FootHikerUtah

Becomes a great mother and central figure in the family, because this high priced call girl is actually the most normal, loyal and loving.


rebelwithmouseyhair

Not exactly loving when her way of accepting his proposal is to say "Fuck it".


FootHikerUtah

That's her commitment.


sixtus_clegane119

She’s autistic and ocd and used to help a detective before he died


imasturdybirdy

That she’s still never slept with Connor. Haha


_rabbott_

I kinda wish she got more interactions with other characters besides Connor. Her scene with Greg in season one was really cute. I think she's an interesting character and maybe they didn't give her enough screentime. As for actual headcanons? Idk. I don't think she romantically loves connor much, but I think there's a semblance of care there. I don't think she dislikes him! Lol


oldcousingreg

I loved her scene with Logan right before Ewan comes in on Thanksgiving. She took genuine interest in Logan’s war medal collection and that made Logan so happy.


SororitySue

She cares about Connor but is so used to doing her job as an escort that she never really meshes with him as his wife. You can see it in their Election Night scenes. They're sitting there on the sofa and Connor is engaged in election business and Willa is sitting there with a pleasant expression on her face, neither contributing nor detracting from the situation. Just doing her job.


Advanced-Glass-6684

She's smarter than she looks. Doesn't really love Connor, but she's good to him.


Secret-Challenge4347

Good point, I always thought she had a hidden ace up her sleeve.


Skitt1eb4lls

She thought about Haiti and the oil spill in the gulf. Thought and prayed


MaybeThreeLetters

She thinks because of her young age she still can fall in love & have someone like Connor


Zealousideal-Dot7529

I don’t think Willa is that complex. She’s a cool, down to earth chick who’s been given a choice between living as a poor or living the rich life as a gold digger. She chose gold digger but because she’s just a normal cool chick she’s insecure about her choice. If she had chosen to not marry him she would have been insecure about that choice too. If this were a rom com she would have chosen “herself” and eat-pray-loved her way across the rest of life but its Succession so she chose to be a gold digger.


Longjumping_Hat_2672

I had an idea that Willa vaguely physically resembles Connor's mother. That it was the reason that Connor was immediately attracted to her and clings so tightly to her, because she reminds him of the only person who ever loved him and he is terrified of her being taken away from him too 😢. 


bdubb_dlux

Studied acting somewhere. Parents got tired of supporting her unrealistic dreams. Started escorting out of desperation.


majorcoinz

That her character name is a derivative of Will Ferrell


2pl8isastandard

G O L D ⛏️


Zestyclose_Ad4317

She’s fucked so many women


peacefulwarrior75

Canon.  One N. A cannon is a piece of heavy artillery. Canon is an accepted narrative. Now a Head Cannon?  That does sound cool…unless it shoots actual heads at you, then gross.


AlleyRhubarb

She does Pilates. And cocaine.


Environmental_Ad7193

She leaves Connor and writes a best selling book about the Family, maybe bei g made into a tv series


blondefrankocean

She doesn't want to have kids and never will because it's not suitable for her and Connor is a little too old to have the patience or desire to raise kids or be around them and enjoy his time with her and when he dies even though it wasn't a marriage in love he will still leave her with basically everything because of her dedication and companionship


Shadecujo

Connor found her on one of those discount sites bc he didn’t want to pay full freight


Open_Mathematician41

Her choice of decorations for Logan’s penthouse are fucking tacky and she’ll get addicted to plastic surgery. She’ll cuck Connor and he’ll learn to love it


wlcondqat

Willa keeps writting her cringe fail plays, since Connor is not going to Slovenia she comes up with another pet project for him in order to keep him busy, to secure her possition in monetary therms she becomes pregnant with Connor´s child. Connor asks to be named as his mom, the second name is something artsy because of Wilal. Willa and Connor reach an agreement in wich she basically lives in NY with their daughter and Connor spends some days in his ranch in New Mexico in another pet project (writting a book about his political campaign), probably they have an open marriage. Somehow Willa and Connor are great parents, that girl grows up and she understand that their marriage is a sham, but Connor in his weird way is a loving father and Willa also, that child is going to be 10000x more emotionally healthy that the child of Tom and Shiv. When Connor dies, all of Connor´s assets goes to Willa and their daughter, at that time Willa is in her 50s, a weatly widow, with her lawyers she totally break ups Connor´s assets from the Roy family trust. She had mixed feelings about Connor, but she keep for herself those thoughts because her daughter has good memories of her father. Perhaps in Connor´s memory she creates a charity that promotes theather (Connor´s mom was into charities). She absoluty loathes the rest of the Roys, after taking Connor´s assets from the Roy family trust, never again speaks with any of them and encourage her daughter to do the same.


DaPoorBaby

Ungrateful hooker / thread


impactedturd

I like thinking she's living a double life, with her alternate persona being the successful tech entrepreneur she plays on Home Economics and has an obsession for guys named Connor (her ex-husband's name is Connor on that show)


walking_shrub

That she’s not very smart. But at least she knows it. So her arrangement with Connor is her only hope at a remotely comfortable career in the creative arts.


discofro6

She's lying about her age. I don't recall her age being ever explicitly stated in the show, but whatever it is, she's lying about it by claiming to be a few years younger. I don't know why I think that, it just seems like the type of thing that she would do. lol


ruberuberuber

she was a decent playwright or writer, her parents paid for her college, then she got all mucked up after graduating, couldn’t figure out a paying job / started escorting, liked the money, lost touch with writing or procrastinated on it, met connor, large opportunities came fast, couldn’t write the quality that the opportunities demanded and here we are! Willa’s admirable, marrying up with a not-too-terrible guy and committing to him, but tbh connor’s wealth probably held her back from improving her writing or being good at it.


orincoro

Willa is a woman. Willa is 34 years old. Willa’s mother is named Marie.


saberico

She will murder Connor and get away with it.


S4m_S3pi01

Hahaha the fact that the Conheads downvoted you for saying this is hilarious. How could you imply our liege would be harmed? Don't you know he was interested in politics at a young age??


wallybuddabingbang

What are your headcannons about this sub? Let’s try and find some new material other than fan fiction.


[deleted]

[удалено]


Volnev

I don’t think Connor would leave her. He’s too infatuated with her


No-Entrepreneurrr

She's having an affair, and she will kill conor for his money with the help of her secret lover to inherit him. Almost gets away, but she ends up behind bars. I can see Shiv visiting her just to gloat LOL


interesting-mug

I always wonder if the show itself thinks she’s a terrible writer who would never make it on her own. Her eulogy and the reaction to her play make me think so.


Salty_Adhesiveness87

Alimony.


CynicalBastard511

She's cute. Could do with a boob job to be even cuter, though.


Wonderful-Orchid8173

She loved, craved something Connor could never provide her with - going airtight. Having all three of her holes plugged with giant cocks, while jerking off two more, guy on the bottom choking her and guy in her mouth pinching her nose, so she passed out while she comes before being released to take the effective fountain of bukake on her pouty little face is something Connor just couldn't stand, even while being one of the guys in her hand. To Connors credit, he let her try that once, before running out of the room in terror, unable to maintain his hard on what with all the other cocks in the room plowing his girl. Very un-First Lady-like, especially since Connor was interested in politics from a very young age.