Personal Shopper
It just struck me that a lot of the more superficial privacy concerns (e.g., Facebook knows what kind of coffee I like!) would be considered positives in a personal assistant or a personal shopper. Although I suppose a personal shopper who then sold that intelligence to junk mail companies might be the better analogy to what goes on online.
But if you think about it, there are some similarities with the sort of romanticized small business owner who knows your order and when you like to come in. And I really find depersonalized or swing-and-miss advertisements online to be more annoying than properly keyed ones. Like, I don’t want to see a week’s worth of livestock medicine ads because I did a search on swine flu.
It’s especially annoying when I buy something on Amazon and then they advertise it to me for a week afterwards like I didn’t really buy it. I know this stuff is hard to do at world-scale, but come on, you made the sale already.