I find it interesting how this game is set up where even if you choose to take the "Good route", you'll constantly be reminded that it's a lame thing to do, based on the character interactions. It's as though the dev herself has some preconceived views of what is and what isn't inherently boring, despite it all being rather subjective.
Ashley feels more like a valley girl who forces herself to confirm to social norms, not because she herself believes in them (whatever the dialogue might say), but because she is too afraid to go wild. It doesn't feel like you are playing a goody-two-shoes character who goes 'bad' over time. Instead, the character is probably naturally more perverted and you are simply removing her chains one by one. That is a big difference.
The male characters are portrayed to be what many people assume men to be rather than how they actually are. Take Jack for example, he's pretty much a more intelligent version of what modern society considers to be an "alpha male". The reality is that there's so much more to these types of guys than even they claim about themselves.
I was stunned when I joined a popular bodybuilding forum and found that many jock-types weren't really dumb muscleheads with a one dimensional personality. They were actually deep critical thinkers and concerned with how hedonistic society has become, etc. Sure, some are total playboys, but even they say the reason for this is because that's the way "the system" works, so they just play along.
This is merely my analysis, I'm not really judging the dev in a negative light. It's just some food for thought.