And it's always seemed to me her want to please was born out of obligation more than desire.
or she evolves past this weird sense of obligation to follow her family's choices above her own
This sense of obligation is only weird from a westerner's point of view, but make a lot more sense if you recall she's from a rather traditional family and was sent to a school where she was essentially groomed to be a
Yamato Nadeshiko. Specifically from that page:
Being a yamato nadeshiko revolved around the Confucian concepts of Feudal Loyalty and Filial Piety, which in the latest wave of Confucian revival meant acting for the benefit of one's family and obeying and assisting authority figures (father, husband, sometimes father-in-law or older brothers, as well as older and/or more respected females). Virtues include(d) loyalty, domestic ability, wisdom, maturity, and humility.
According to the Confucian train of thought, the fact that your parents blessed you with life creates an obligation to them that lasts far beyond the age of adulthood. It's essentially a debt you never completely pay off...that's why even many adults in that environment allow their parents to regulate their life in a way most westerners can't imagine anyone putting up with.
On that note, you can call Lilly-route Hisao many things, but an authority figure he was not.
