Disclaimer: I don't own RWBY.
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Monday
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Monday morning begins with Jaune gets pulled aside by not only by Envy, but also Pride. Pride intends to challenge Jaune to a spar and to test him on his ability. Ruby's supportive of the splitting up with Jaune at this time, confident he'll be able to prove his ability and earn Pride's respect. Jaune fights and trains with Pride all day long, with Envy as a cheerleader and watching in awe and naked admiration.
Ruby spends the morning watching with Sloth and Gluttony, gathering intelligence and working on her gameplan of how to address all the other sisters. Sloth and Gluttony are willing enough to help, once prodded.
Gluttony is bribed by Ruby cooking and sharing strawberry pancakes, and helps explain the Arc family traditions (such as the Arc Words motto of never going back on promises, how their father raised them all on the importance of family first, and the tradition of coming together for dinner as a family no matter the arguments) and the family dynamics. Said family traditions also include the Top Ten- something Gluttony, who's been raised with it her whole life, sees as utterly uncontroversial. To her, Top Ten is just a formality on what she assumes everyone else does as a matter of course (putting family first). To Gluttony, who keeps the genders together for her Top Ten, being 10th (the only spot open if Nicholas is included) is an honor rather than an insult, since it means you're on the same tier with family. When Ruby says that Jaune is the most important man in her life, Gluttony first assumes that her father and uncle are dead, and then finds Ruby's prioritization of Jaune odd- though she rationalizes it that Ruby must already be thinking of marriage. It's the demonstration of the culture clash between Ruby and the family-first Arcs. Being the uncomfortable subject that it is for her, Ruby soon changes the subject gracefully and gratefully.
Sloth is a bit put off at how hard Ruby is working towards this, and bemoans that Jaune isn't the slacker he used to be before he ran off to Beacon. Sloth is a bit more understanding when Ruby explains what Leandra told her- about how she'd only approve if Ruby won the approval of all the girls. Sloth finds Ruby's answer about her Top Ten more romantic, fitting Sloth's own feelings towards her mystery boyfriend. Sloth, who has a secret boyfriend at school, is impressed by how earnestly Ruby is working towards the future, and touched by how Ruby and Jaune are trying to be together. Due to Lust's disastrous dating history, and some bad encounters of the other sisters as well, Leandra is notoriously protective of her children's hearts- hence why Sloth is hiding her own boyfriend until she's sure enough to bring him over for the familiar family interrogation. Sloth finds Ruby's placement of Jaune first romantic in a dirty-secret-don't-admit-I-admitted-this sort of way, and sees Jaune's bringing of Ruby over as proof of his faith in her. Sloth can tell that Jaune is serious about Ruby if he's biting the bullet and bringing her over.
Sloth's assurance of Jaune's interest is appreciated, even if the term 'risk' isn't, as is hers and Gluttony's concern about the broader Arc trial. Ruby waves it aside as Ruby entertains them with the story of what Yang did, tried to do, and threatened to do to Jaune when she found out they were dating.
Ruby is able to 'win' Sloth and Gluttony easily, and caps it with a promise each, a reoccurring thing with the sisters. Gluttony makes Ruby promise to uphold Arc traditions, of the family dinners if nothing else, so that she and Jaune and whoever else would always share home and hearth no matter what. Sloth makes Ruby promise to appreciate the time she has with Jaune, to slow down and enjoy life with him in the present rather than just look towards the future. Ruby's able to easily make these promises and garner their support by early afternoon.
Late afternoon is taken by Pride, who calls Ruby out for the same sort of training and sparring she gave Jaune. Despite having been sparring with Jaune all morning, Pride is barely winded, and it's soon clear that Pride is above Ruby's level- possibly on the level of Winter or Qrow. It's a grueling pace, with Pride offering multiple opportunities to quit and Ruby refusing to.
As they spar, Pride and Ruby talk. Pride was impressed by Jaune's strength and fortitude, and asks if Ruby was responsible for it. Ruby denies it, crediting Pyrrha- and passing a first test of character, since Pride was seeing if Ruby would lie and take credit. Pride remains unconvinced about Jaune- strength of body is one thing, but strength of character is another, and the Arcs need both. Pride also questions Ruby. Ruby's strong, sure, but does Ruby respect Jaune? And why did she like him before he was strong? Why wasn't she honest at Beacon, and see Jaune expelled as a fraud?
Ruby proves her strength by keeping up, and tells how she first started falling for Jaune (or at least respecting him deeply) when he was brave enough to wear the dress at the ball. She'd given him a nudge to stand up for himself during the Jaundice arc, but the ball was the moment he impressed her. That he'd been a true friend to Pyrrha and risked humiliation because of Arc Words. It was the start of what would turn into her attraction. Ruby justifies letting Jaune stay in Beacon because it reminded her of her own pride in her mother Summer Rose, and because of his desire to live up to his family name.
Pride is surprised at both Ruby's parallel and that Jaune took such pride with him to Beacon, allowing Ruby to get a match-winning blow. Pride approves- of both Ruby and Jaune separately, and Ruby and Jaune together. Pride gives Ruby a pass, speaking well of her and Jaune both at dinner, much to the chagrin of the older sisters when they start passive-aggressive bad-mouthing her. Pride also plays disciplinarian in Ruby's favor when Wrath and Avarice re-raise the question of Ruby covering for Jaune at Beacon, forcing them into silence and preventing a repeat of the previous night's fight.
It's a good first day's progress- three sisters down for both Jaune and Ruby, just four more to go- and that night Pride visits Ruby's room to give her advice and foreshadowing for the next day's trial. All Pride asks for in return- Ruby's promise to Pride- is that Jaune and Ruby both hold their head high in their relationship, and never be ashamed to be together.
Ruby is happy to, and goes to bed with happy thoughts... and stays awake long after, as something keeps waking her up.
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Author Notes:
Monday begins the main plot. As viewpoint character, the primary story is Ruby spending time with the sister(s) of the day and trying to win them over. The B-plot, parallel and in the background or the subject of the evening dinners, is Jaune's progress. Jaune being pulled away by the sisters means he has less time with Ruby during the day. The family dinners provide the summary and reflection of progress of each day. A final occurrence is that each evening, the person Ruby 'won' that day and/or Jaune comes to Ruby's room and has a moment of support.
At the end of each chapter, I'll point some thoughts on the OC Sister(s) of the day, including the elements they borrow from the Teams. The sister's aren't direct expies of the canon cast, but they have elements borrow on some level
Gluttony (Nora): A cheerful-spirited, somewhat chubby girl who likes eating 'so that there's more of her to love.' The elements she takes from Nora are her good cheer, hunger for pancakes, and support of her friends (or, in this case, family). Not the brightest person, but smarter than she comes on, the family tradition of eating together as a family no matter the argument has a special significance for her. To gluttony, Food = Love, and so sharing food is sharing love and leads to reconciliation after a fight. Hence why it's important to share dinner no matter what. It's her surprisingly deep moment.
Sloth (Blake): A pretty girl who gets by in life with as little effort as possible. The only reason she has a boyfriend is that he put the effort to ask first. Enjoys lazing around, never wasting time because she enjoys every bit of it. Also a closet romantic with her romance novels. The Blake parallels should be obvious- if Blake were human, had a loving and protective family, and was kept far enough from the world that she could ignore it. Sloth is the Arc sister who comes closest to breaking the mantra of family first- though she (comically) approaches the prospect of liking her boyfriend more than Dad as if it were taboo.
Pride (Pyrrha): A mature, stern, powerful champion of the Arcs. A visual mix between a gender-flipped Jaune and Pyrrha, if Pyrrha smiled less and was the Champion/fighter persona most of the time. And had a thing for pants and pockets. Pride is a contrast to Pyrrha's style but with the same intent- hard and challenging rather than soft and supportive, but with the same intent of building you up by giving you a chance to prove yourself and push your limits. Once you break the stern shell, a somewhat sillier side emerges- proving there's a blond goof within the armor, and someone who's had her own unrequited love.
In truth, Pride as a sibling-character came before Meet the Arcs: her real name is Joan, and she's the oldest sister/major OC from the eternally unfinished project of mine 'A Family Friend.'