In my Maya play through I don’t see why the MC needs to tell Josy anything, personally I have 2 positive points with her and refused to buy anything for the dinner, asked why she called, told her to find somewhere else to stay, pretty much everything opposite to make her like the MC less. If she is really that thick that my baseball bat approach to fending her off didn’t work...
I agree that In my neutral paly through it can be difficult for the MC to work this out. Haven’t chosen 1 girl to focus on.