I guess Cortana could engage with people who do not have personalities, for example: tech nerds, Hillary Clinton fans, Canadians, but there is absolutely no chance it could hold its own in one of the fast moving, philosophically diverse conversations we bohemian intellectuals who regularly convene at the Albion Inn, Blackburn, Lancashire to enjoy.To put that another way, it’s a machine, just a machine, , a software engine — nothing more. It cannot extract meanings from words input to it, only respond to keyword triggers.
It might well be able to reply to a request to turn on the TV by asking, “Which channel would you prefer to watch,” but how would it deal with sombody asking, “Hey Cortana, what do you think of Immanuel Kant’s proposition that while objects exist in reality, only a human mind can surround them with time ans space?”
I guess that unless an author had written a reply to that specific question it might struggle for a primary response, and if an answer had been placed on the database, Cortana would be completely stymied by the follow up questions.
I have no exposure to Cortana but my experience of digital assistants it they’re just plain annoying.