There was that (in)famous NYTimes article from a few years ago about how the target supermarket was successful in finding out a teenager's pregnancy before the girl's father did, and sent her coupons for baby items (which is how the father first got wind of the likelihood of his daughter's pregnancy).
So, as the OP says, it gets murky and grey very quickly as you get into "personalised" selling.
We "live in interesting times" indeed.