Short version: I need a plan to humiliate the Jolly Time Girls that's suitable to a Calistrian and not misogynist.
So this went super badly at my table and I'd like advice on how to mediate it.
Basically, I'm actually using the gangs of Old Kintargo to generate plot. The Logrunners will be selling drugs to the students at Alabaster Academy. The Flower Shop Crew will face off with the party Unchained Rogue in recruiting informants and blackmail. The Magical Girl vigilante is trying to enter the Lacunafex. And so forth.
The Unchained Rogue just took a level in Inquisitor to enter the Calistrian religion, with a long-term plan of Evangelist prestige class, which will allow him to advance either the Rogue or the Inquisitor abilities.
So, to connect to that underground faith, I had the hook be that the High Priestess leave a packet at the URogue's drop point: a drawing of the three Jolly Time Girls and the message: humiliate them. The gang of half-orc female barbaraians has been scarifying beautiful women, which has affected the sacred prostitutes of the Calistrian faith. This is sort of an initiation test for the PC.
One male player suggested murder, of course. Another male player suggested a punitive beautifying of the gang: mumus, makeup, etc.. And then the female player said that this plan would be misogynist and transphobic. The male players then recruited her character, a Magical Girl vigilante enrolled at the Docur School for Girls, to teach them what a mean girl would do, which did break the real tension at the table, so there was some discussion of using emotional violence. But she was kind of against those tactics too, not least because of the time involved and the fact that those mean girls are Sarinis and her non-vigilante identity's antagonists. She thinks simply getting them arrested or just murdering them is the best solution.
Things were getting tense as the time for the night was running out. I called it, did some narration, said that the party would reconvene the next morning with ideas.
So, how do I salvage this? Convincing the female player that forcible feminization of the half-orc girl barbarians is not misogynist is not a viable solution here. What plan could work for a religion that uses slander, gossip, humiliation, and public shaming to discipline outsiders?
More generally, how do I role play this faith going forward in ways that can guide the players away from this kind of conflict again?
Calistria os not only about sex. She is also the goddess of trickery and thieves. You can focus your humiliation on this aspect.
If the Jolly Time girls are a gang, ruin their reputation !! Make it so that their allies all get arrested, and then spray the rumor that it is because these girls are telltales. Kill a lieutenant of the local crime boss, and let clues that all lead to the Jolly Time Girls. If you combine these 2 ideas, you can make the crime boss believe that the girls are planning to take his place.
A last option is to try to saw discord among the girls, suggesting that one of the girls is stealing from the others.
Humiliate them by defeating them in combat, but leave them (preferably) alive. Shouldn't be hard at this level (if they're just starting the AP around 4th level they'll need to be more cautious). Preferably this is done primarily by a female character who fits their description as offensively "pretty". Double down on the threat that if they continue their attacks, you'll wipe them out. Leaving them powerless will destroy their credibility as a gang. If they choose to continue or retaliate, make good on your threat.
Sometimes it's best to keep things simple. If that tactic is too combat oriented for your group, you can achieve similar results using social tactics to undermine their credibility and reputation.
This also avoids the area of discomfort your player was having.
I think you're on the right track - whether a rational argument could be made on whether the beautification of the Jolly Time Girls is misogynist is beside the point, it's annoying at least one of your players.
I suggest you steer them away from that approach on practical grounds: How easy would it be to accomplish in the first place? And if they were successful, what are the likely ramifications? Is it at all reasonable to assume such an outcome would dissuade the Jolly Time Girls from the behavior Calistria objects to? That seems highly unlikely - more likely it drives them to do it more.
Part of this came from you (the OP) - you gave the proto-inquisitor an explicit instruction to humiliate. Probably better to have given a more open ended mission: "Put an end to it. Punitively. And send a public message that Calistria does not stand for this behavior."
You could also encourage the group to make this work for the Silver Ravens. The Ravens are there for Calistria worshippers (an outlawed religion that still has adherents in the city) and are taking care of problems that the corrupt and self-absorbed Thrune regime doesn't care to address.
Yeah, I set the conditions necessary for this to be a problem as the DM. In my own defense, I was trying to be authentic to the Calistrian faith, which polices outsiders through gossip, slander, and public humiliation. I was also trying to open up non-combat options, as this Unchained Rogue 3/Inquisitor 1 PC would never win a solo combat against three Barbarian 3s, and a one-on-one fight would be iffy--one crit with those great axes... I hoped this player's lone wolf would either work independently but creatively or go back to the group.
After a day to cool off, the female player's come around to defeating them in combat, as a way of humiliating the combat-focused Girls. It would be especially good if her high charisma vigilante did it, of course, but that wouldn't really fit the design of the encounter, which was to give a spotlight to the Calistrian character and introduce him to his new-found faith. The male PC needs to demonstrate his worth to the Calistrians, as it is his introduction to the faith.
I also agree that the Calistrians are a good organization to reach out to, as does the female player who wants to know why a private vendetta should be SR business, which was not brought up at the table because we didn't have time. It work especially well thematically. This book's adventurers will also be about religion: the Rose delivery was delayed to now introducing the Milanites, the Mahathallah cult, a banker of Abadar delivered the sixth level organization gift of 750 gp per PC, etc.
Sowing discord among the girls might also work.
To clarify, I wasn't suggesting that the other party members not contribute (be it a combat or social encounter), only that the character who most offends their sensibilities be prominent. Never split the party and all that.
I think as described, using social means fits your party well. I assume the gangs of Old Kintargo are viciously competitive, so the party could probably accomplish their goals without rolling initiative. But you know your group best.
Really anything that makes the three specific Jollytime Girls look weak would suffice, even if just to their own gang members. Unfortunately the book doesn't spend much time fleshing out their motivations and such.
Also, as far as I was aware the Calistrans of any note had been driven out or wiped out by BT. Have you created your own faction? I can't see a Thrune tolerating a CN religion, especially the savored sting. They did hand over their temple to Abadar after all. The wasp's nest was abandoned for some time, and that's the only hidden Calistran shrine I can think of.
Once a player showed interest in them, they became merely a very underground group.
Having the gangs of Kintargo go into a gang war sounds like something that would work, although there's two players who're a little too lawful to take that kind of risk.
No need for a full scale gang war, honestly just getting them in trouble with their own gang (if we're just talking about dealing with the three specific members). Honestly the Jollytime Girls may take care of the problem in house.
Since there's really very little information on the gangs, it's kind of up to your discretion. So if you don't mind, what have you come up with?
I decided that those three Jolly Time Girls were the gang, since there can only be a maximum of about 100 half-orcs in the city.
Lacunafex is a ridiculously powerful student council straight out of anime, led by Lady Docur herself as head of the school.
The Diola Brothers monks were going to be bullies and Queensmen, leading to a street war with the Qs.
The fetchling Flowershop Crew were going to be blackmailers and info gatherers for the underdeveloped Nidal faction.
The Logrunners will be straight drug runners, there if the party wants to make the mistake of a War on Drugs.
The Spellcrafters I want to use to spice up combats, but I'm not sure how to use them yet.
Black Eyes will be like mini-Punishers or the low-rent copy cat Batmen from the second Dark Knight movie. Just to irritate the team.
Oh, if it's just 3 of them total (there's a dozen or so in my Kintargo) the PC's don't really need to worry about retaliation from a larger gang.