Loving the concept and what I've seen so far of this. Couple minor bugs -- your probably aware of them, but just in case, here's one that leapt out at me:
So I picked the friend's brother route, as the whole step brother thing wasn't my cup of tea. On that path, there was a problem where some of the text seemed predicated towards the step brother path, unfortunately, i.e. this here --> ""His name is Ruin, my mom married his dad a couple of years ago." You say holding your breath a bit at the judgment that the soon to come after, you knew it was wrong to have these types of feels towards your Madison older brother but you couldn't help it."
Also, in the beginning, when I try to set names and such and then use the hyperlinks to do character descriptions, the name becomes unsaved.
Anyway, good luck with the project. The story feels strong and interesting, and certainly relatable for most of us.