"I'll go with the Bad Boy! I want long hair, and stubble that isn't quite a beard." He does not have to take this time thinking about this question, instead answering immediately.

"Excellent, excellent… Okay, our next role option is for your fiance. The male options are the Prince Charming, the Dark Rival, and the Noble Prodigy. The Prince Charming is earnest, sweet, and upstanding; the Dark Rival is, well, a bit of a dark rival to the Prince Charming - less earnest, more mean, though not truly cruel, more dangerous - and the Noble Prodigy is - mm, a little out of place, compared to the others? He's already graduated the Royal Academy you'll be attending and made somewhat of a name for himself. He'll be hardened from his past and reluctant to open up emotionally, at least at first. There are also female options, if you'd like to hear them - technically, the role genders all count as one thing for the purpose of Flexibility."

"Since it's not an extra cost, I wanna hear the female options before I make my choice."

"All right. The female options are similar enough to the male options - you've got Little Miss Sunshine, the Social Climber, and the Action Girl. Little Miss Sunshine is optimistic, friendly, and idealistic. The Social Climber is soft-hearted deep down, but has a determined, cool exterior. And the Action Girl is - well, it's all in the name, isn't it. You can have her be a distaff counterpart to the Noble Prodigy or you could have her be attending the Academy at the same time as you. If the incentives line up right, she may have a history of disguising herself as a man in order to be allowed into the military, but that's not a requirement."

It is time for the paper and pencil to come out again! Alistair spends a while scribbling out a pros and cons list, scratching out options, erasing and rewriting things, and so forth.  Eventually, he reaches a conclusion and sets his scribbling aside.

"I think I'll go with the Action Girl, and have her be in school at the same time as me."

"Great. Now we've got the options for your rival's Role, and honestly, they're pretty much the same between the male and female forms. There's the Poor Prince-or-Princess, the Hero's Daughter-or-Son, and the Extraordinary Commoner. The Poor Prince(ss) is - royalty, but not in a way that means they have any power. Maybe they're from a different kingdom, maybe they're the half-sibling of the Crown Prince but their mother was executed for treason, maybe there's some other equally compelling circumstance that keeps them from being able to inherit. The Hero's Daughter/Son was born to a common family, but their father or mother accomplished some heroic deed that posthumously elevated their whole family to a noble rank. And the Extraordinary Commoner is someone talented, clever, and determined enough to get into the Royal Academy on merit alone."

"I'll go with the Hero's Child... Let's say Hero's Son, even though I'm not actually attached to gender one way or the other."

Nod.

"Okay. There are a couple other characters to make decisions about: your trusted Allies! So, you get two to start with, but you can have more as many times as you want to take the advantage for it. The types are Servant, Butler, Classmates, Admirer, Animal Companion, and, since you've got an appropriate Time Period, Artificial Intelligence. They're all pretty much what they sound like. Your family will likely have multiple servants, but the Servant ally is yours: your age, loyal to you, and a cut above in skill, both in their actual job and in extracurriculars. The Butler works for your family, rather than for you - they're older, for one, and are more a source of advice and support than an instrument of your will. The Classmates are two people who mechanically function as one unit - they can be your ears and eyes when it comes to picking up gossip that people might not want to say in front of you, or in doing social maneuvering that it'd be suspicious for you to engage in personally. The Admirer is a classmate who carries a torch for you - unrequited, and they know it, but that doesn't stop them from being putty in your hands. Since your Villarosa is High magic, your Animal Companion can be either a particularly well-trained creature or nearly as intelligent as a person. And if artificial intelligence is common in your Villarosa, the Artificial Intelligence ally will be superior in some way."

The papers have more details. 

"I want an AI." He says immediately.  "As for my other ally..." he trails off, finding the relevant page and looking it over for a moment, occasionally scribbling on his paper.

"I think I want the Classmates for the second allies." he says eventually.

"Solid choice. Do you have any flavor preferences for the AI? By default it's like a fusion of the Butler, Maid, and Classmates - loyal to you, inclined to do your bidding but not overly servile, excellent at collecting information - but there's lots of directions you can go with it. You can also decide if you want it to be an upload or a true AI. As for the Classmates, those will by default be indebted to you in some way, but it can also be the case that you just charmed them with your natural leadership skills."

He takes a moment to think it over.

"I think I want the AI to be mostly a strategist, although I would appreciate some information retrieval ability.  And I want it to be sufficiently loyal to me that I never have to worry it will be turned against me by persuasion.  Indebted classmates are fine."

"Don't worry, while it is possible in theory to alienate any of the Allies, their personal loyalty is assured at the start of the story. All options are fond of you on top of any practical obligation such as employment. I'd say the Butler, Admirer, and Classmates are most likely to make decisions that displease you in some way, but it'll almost certainly be because of human error or them trying to protect you rather than a betrayal. And - hm, this is less of a guarantee, but they are allied with a villainous character, so while they can certainly have principles, typically they'll be aligned with your own, or less important to them than their relationship with you. Again, this applies less to the Butler, but - ah, I'm rambling."

Sheepish smile.

"Shall we move on to the matter of your Fate?"

"Yes, assuming that begins with an explanation of what, exactly, you mean by Fate."  He sounds distinctly concerned as he answers.

Nod.

"Fate is, in this case, the bad ending for your canonical counterpart's route. There are six options, the most severe of which earns an additional advantage and the least severe of which necessitates an additional drawback. There's a more detailed explanation on your paper."

Disgrace: The least severe option. You retain your rank and status, although your reputation is permanently in tatters. You probably won't be invited to rub shoulders with the upper crust, but you still have your money and title. Requires one extra drawback.

Nunhood: Yes, that's totally a word. After your fiance calls off the engagement, you are forced to stay in a convent and become a nun, taking vows of chastity, poverty, and service. 

Exile: Whether you're unceremoniously married off to a foreign noble in a last-ditch attempt for your parents and family to save face or simply shown the proverbial door, this Fate means you'll be banished from Villarosa, never to return to your homeland.

Poverty: As though it wasn't enough to simply lose a valuable engagement and watch your fiance marry somebody else, you lose your title and riches and are forced to work for a living starting from next to nothing. Although it's very much possible for you to make the best of this and have a happy, successful life, you'll never be rich or noble again.

Servitude: In addition to being stripped of your title and wealth, this Fate forces you into the service of your rival. This can range in severity from being a paid member of her staff to slavery, and much of your treatment at her hands will depend on her personal preference. Keep in mind that if your Villarosa has the right technology or magic, this may be used to ensure your obedience.

Death: Whether you're executed for your crimes, murdered by your rival or fiance, or suffer karmic retribution as the result of your own schemes, by choosing this Fate, you wind up dead at the conclusion of the story. Entitles you to one extra advantage.

"I think it's worth noting that you can't declaw the canonical versions of the Fates. I've seen some reincarnators set up their escape from the canonical timeline to have an event that superficially resembles the canonical Fate, but that's tricky. To use an example, while it's possible to set oneself up to temporarily die and then be revived, the actual Fate of Death means that you stay dead - any people you arranged to use resurrection magic will be convinced or forced not to, any artifacts you've set up to recapture your soul upon your death will fail, and attempts to revive you will fail. It'll be up to you to avert this. Does that make sense?"

He relaxes some as he listens.

"So, my Fate is what happens if my fiancee chooses the hero over me, but will be averted if I win.  I suppose that gives ample motivation to ensure I win, then."

He reads through the list, writes on his scratch paper for a moment, and then looks up at the angel.

"I'll go with exile, of the non-marrying variety."

"Okay, I think that of the purely mechanical choices, all that's left is your set of advantages and drawbacks. Remember, you get four advantages free - I've already marked you down as a Magical Prodigy and my supervisor approved substituting one of the free advantages for being an Enhanced species, so after two others you'll need to take drawbacks to balance them out."

The paper has a list that's a lot like this, although without Yuri Heroine and with less gendered language ("Goddess of Beauty" and "Feminine Wiles," for instance, are instead "Supremely Beautiful" and "Master of Seduction"). There's also Flexibility, which the angel described earlier, and something called Vending Machine:

By default, all non-you characters are either new souls or reincarnators selected for being able to fit well into the plot. With this advantage, you may pick any character, including but not limited to your fiance, your rival, your parents, and your Allies, and select any person, real or fictional, to fill their role. Real people will be drawn from the moment of their death, while fictional characters may be slightly different from the fictional version as they will be drawn from the closest matching universe to the canon you specify. This person won't retain their memories - ask your representative about past life recall options if you're interested. You may take this advantage more than once.

As far as drawbacks, there's no Patriarchy or Matriarchy option. The drawbacks Ditz, Jealousy, No Compromise, and Spoiled Rotten are absent as well, instead being replaced by one called Flawed Personality:

By default, your own personality is preserved as closely as possible. With this drawback, you can choose some sort of unappealing or otherwise undesirable trait, such as stubbornness, jealousy, bossiness, impatience, or anything else you think of, to be applied. Note that, while no personality trait is always a disadvantage, if you take this drawback, whatever trait you select will come back to bite you more often than not. You may take this drawback more than once.

There's also Wrong Genre Savvy:

Go back to the list of potential Genres and choose an option other than the one you picked, and your memories of this planning session and of The Roses of Villarosa's canon will reflect that new Genre. No matter how many times events contradict your memories, you'll be inclined to chalk the discrepancy up to having misremembered the events or something having failed to go according to plan.

He spends a while looking over the paper, taking notes and drawing diagrams as he goes.

"I definitely want Battlemaster, Bad For Her, Unearthly Instinct, and Silk Hiding Steel.  I'll take Dark Secret and In Character as flaws- unless In Character is much worse than it sounds."

He considers his page again.

"How would Save The World and Off The Rails interact?"

The angel thoughtfully laces their fingers.

"The compulsion to stay In Character doesn't directly affect your thoughts or force you to undertake specific actions, but there's still a lot it can do even without that. It acts mostly on Fate, and - it isn't quite the same as Ghost in the Flesh in that your canonical counterpart is literally inside your head with you, but it can certainly remind you how he would feel about things or what he'd be tempted to do in your stead. It can also make certain actions or inactions feel more difficult. On the plus side, it relaxes based on how alone you are - it's less prominent when you're with your trusted allies and absent entirely when you're completely alone. But, well, a lot of people who take this drawback experience a little of the 'fake it until you make it' principle."

As for the next question:

"Well, Save the World poses a threat - not necessarily to the world itself, although since you're in an Epic it's more likely to be on a massive scale, and Off the Rails means that it's much easier to divert events from the plotline, for better or for worse. So you might be able to kill or incapacitate your rival where in canon this would be nigh-impossible, and this could either allow you to take his stead as the hero of the conflict or it might doom your entire kingdom. Or any number of possibilities, of course."

"Oh! That's not as bad as I'd expected! I'll definitely take In Character.  How different from me is my canon counterpart, anyway?"

He hums thoughtfully, growing more serious as he looks over his notes again.

"How much of a disadvantage is it to lose the guidelines provided by knowing the plot, if I take Off The Rails?"

"Well, that's part of what we're deciding now. Obviously his childhood and background will be different, and he'll have to be the kind of person who could organically make the choices that support the plot, but for several reasons we don't want him to be so different that, if you weren't taking In-Character, people would suspect that you had gone insane or been possessed or something when you regained your memories and started acting more like yourself. It's not a strictly mechanical choice, but you can definitely decide details of the story so long as they don't contradict the required plot beats and how exactly your canonical self will slot into it."

The angel thinks for a moment.

"It depends. The knowledge of specific events and when they'll happen will be thrown off, of course, but most of the information about the world that you'd learn from knowing the plot will still be true. So - to take the plot of Star Wars as an example, you might divert the actual confrontation between Luke Skywalker and Darth Vader at Cloud City, but Luke would continue to be Vader's son."

"I'll take Off The Rails and Save The World as well, I think.  As for what my canonical counterpart will be like... well, lets start with my Dark Secret."

He pauses for effect.

"My father is not merely a merchant, but the owner of the largest and wealthiest trading company in VIllarosa.  He did not start this company- ownership of it has been passed down through the family for generations.  All of this is well known- what is less well known is the source of our vast wealth.  The family has used dark magic to eliminate the competition and direct the minds of potential business partners, and even to cover up our involvement in the criminal underworld and trade of illegal goods.  There is an ancient family tome of dark magic, which has been passed down through the generations, and with my departure for school, this tome has been given to me.  If the tome is discovered and I was able to hide it's origins, I would be expelled from school and risk the dissolution of my engagement, but were it linked to my family and the means by which our wealth was gained discovered, the company would be dissolved, my father put away in prison for life, and my mother and I would both be left destitute."

"Speaking of my engagement- I understand the personality archetype my fiancee has, but is her background pre-determined?"

The angel nods along.

"That works well, especially since there are multiple failure modes associated with it. And no - you mentioned you wanted her to be roughly your age instead of having already graduated the Royal Academy, so there's that, but if you've got ideas I can certainly pass them along."

He considers for a moment.

"She is, actually, a noble- the third child of a Duke, who's duchy is a prosperous and beautiful planet.  The engagement was set up in large part to solidify a deal between her father and mine, though we knew each other prior to the engagement and like each other- she's not looking for a way out of it.  Being the third child may lessen her political influence, but it meant her parents gave her more free reign, and she's been getting weapons and combat training since she first started showing an interest, and has recently been allowed to go on unsupervised adventures across her home planet, at least one of which I accompanied her on."

He looks over the notes and papers in front of him.

"Bad For Her, Good For You lets me choose the hero's bad ending, from the same set of options as my own bad ending, right?"

"Okay. You'll want to keep in mind that regardless of how much your fiancée likes you as a person, she's still going to, or at least highly likely to, fall in love with your rival. And we can't push her regard for you all the way to romantic love at the start of the plot without you taking the associated advantage. But ensuring that you know each other well is smart."

The angel beams.

"I was just about to get to that! So, yes, you can choose any of the Fates to subject the hero to, with the exception of Disgrace. I'm honestly not sure why - my best guess is that he simply has less to lose than you do, but it might also be that Disgrace is the least damaging of the Fates and the anticipation is that most people who would choose this advantage in the first place aren't interested in that."

"Oh, I know, I just figured that it would be easier to keep someone engaged to me if she only wants to leave for the other guy than if she was actively looking for a way out of the engagement." he replies.

"As for the Hero's fate, let's go with Servitude."  This is a much less nice smile than his previous smiles!