What I have been reading and dreaming are scaring me

In preparation for our impending trip to Tokyo, I have been reading guide books and street blogs. The book began well enough, but when it got to the shopping and the bars, it became clear that the book and the city may be too overwhelming for me.

Overwhelming because Japan, with all of its high tech inventions and freedom of expression, is still a feudal society where the women and the poor are left at the margins. For instance, certain bars only patronize a certain clientele and women are forbade at certain areas and institutions. People operate through introductions and who they work for. They rarely interact outside of their small circle of family, friends, and coworkers.

I can't understand how any society could choose these rules- so limiting, so stiffling, but all societies do and I can't help but question, where can the tender-hearted, the idealistic go?

If it is not New York (too loud and too expensive), Paris (where is the literati?), or Tokyo, where is it? Is it Austin, where the self pronounced "hipsters" could annoy anyone to death? Is it Detroit, where a single female can buy a house for $25, but cannot walk the streets alone? What about Portland or Seattle? Is it the buzz of Berlin or Budapest?