I'm less worried about the creepy factor, and more about the nuance that I think would be hard to encapsulate in a user profile. There are a lot of complex factors that go into a decision. It can't be boiled down to "I always want to fly United, and I must have an aisle seat." Or "Italian is my favorite kind of food." There are a ton of other factors that go into the decisions, and those factors may change day to day. One day I might choose a different airline than usual because they have a nonstop flight. The next day, I might decide to stick with my primary airline despite two connections because I need the miles. When I choose restaurants, I often like to skim the yelp reviews -- not choosing solely on star rating or cuisine, but on the comments. I don't know how a virtual assistant could navigate this kind of stuff, even with tons of data about me.
