I believe you're thinking of
Charm School from
Hanako Games. Unfortunately, many of their early games are
no longer supported, and I'm trying to figure out if they can still be bought. If not, well, I'm sure there's some other way of playing the full version.
I know Charm School is later than you said (2003), but most Western-made games in the vein of Princess Maker and such didn't start appearing until after the turn of the century. I suppose it's possible you're thinking of some very early RPG Maker title or something even more obscure, but I'm fairly confident with this guess.