Ive tilted at this particular windmill many times and it’s a bad habit of mine to assume meta reasons for storybeats I have an issue with rather than it being done with good intentions.
Like Maya/Josy allowing him to date other people. Being “casual”...to me that wasn’t a character choice it was to put them in a holding pattern. It kicked the can down the road for explaining why they were in a relationship halfway through the plot but ok with him sleeping with anyone. Messy to write two paths so just have them be in an open relationship and always having hidden encounters (Maya in the library? Public sex in bushes? Pantie peaks under tables?) easier to write and isolates them from other girls.
Tybalts blackmail was dubious at best and her response was out of character. I personally (and as I said, I’m jaded and always assume the worst) think the blackmail was a tool to explain why you’re not public with Jill. To ease the writing and keep public opinion uniform. Going forward you’re either functionally broken up or pretending to be. Easy to write and again isolates her.
Bella coming around on the MC, letting him call her Bella, after the Cathy incident is easier to write than having Bella dislike the MC if you didn’t pass her check earlier in the story. She now likes all MC’s. Sage becoming your friend out of the blue if you entirely ignored her because she respected you don’t wanna bang her...
It’s cynical as fuck but a lot of my problems with this stories writing isn’t because DPC can’t write, it’s because I personally think he has bitten off a whole lot more than any solo Dev could ever chew and has to cut corners to ease the writing.
there are plot requirements that we have to accept.
all the LIs between the fourth and fifth chapter tell MC that he can have appointments with others (except Bella, who can't expect anything), even Jill tells him that she doesn't like it but accepts it (out of character).
this naturally served to leave history free to go in any direction.
but now things have already changed quite a lot.
we have gone from a phase in which the LIs were more or less aware of each other, to one in which the circle of those who know has widened considerably.
all DIKs know about Bella, all HOTs and Jocks know about Sage.
furthermore, through that unlikely twist of Tybalt's blackmail, MC either lets go of Jill or declares himself. and feelings of guilt arrive and Derek goes to MC to lecture him on his sister's happiness.
it is a highly unstable equilibrium.
DPC has moved on to a MUCH more ambitious story than AL, and is struggling with it in keeping the various stories up to date. we must have a little patience.