I talked about this a bit on my Discord, but basically, after a certain point some routes will just close off because it doesn't make sense for them to continue. Like, if you didn't take the dark path with Character X at junctures A or B, then why would you at C?
Like.. Let's take Gabby's friend path, as a neutral example. Let's say you've played the last several chapters only being friendly with Gabby. I don't think it'd make sense to then have your character suddenly have the option to be a raging dickhead. Buuuut, it may make sense for the player to see her in financial need and say, "Hey, maybe it's not your thing, but I'm doing this calendar, and I could pay you for it. You just need to be naked." Or, "Well, if you ever wanted to make some extra money, I could use someone to accompany me on dates. And if you wanted to make even more money, well.."
Both of these scenarios could lead to the player having a 'corruption' style relationship with Gabby, where the dynamic is really one the player is taking advantage of his wealth in a way that's morally dubious, but not really capital-e Evil.
Likewise, if you've had a purely romantic relationship with Ashe, with no pushing of her boundaries or anything, the character likely won't turn on a dime and decide, "Well, now that we've been dating for a month, I can be a real jerk." I feel like that time's basically come and gone -- either you've decided to have a toxic relationship with her, or not.
I want to keep the freedom for players to adjust in good and evil ways, but there is a limit, both in terms of workload, and what the narrative will support. There's going to be a little time-skip in the game soon, and I want to have a few characters pretty firmly established in their feelings towards the MC, by the time that happens.