Why do you think that's the complaint? [...] And here's where I think you go really wrong. I'm not all that good a telepath
It's not telepathy. Those are the complaints voiced above. You'll even find the "amateur social engineering" bit I quoted in this thread.
If Cortana doesn't behave right unless I treat it as I would a female colleague, that's a problem with Cortana
This is where we differ. The program is designed to simulate a personal assistant. Why would it act in any way contrary to that purpose? Why would you want it to act any other way? If I go to the store and buy a video game, should I complain that it makes a lousy word processor because of some belief I have that software should do what I want, regardless of its intended purpose? I don't understand this complaint.