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Re:After GDPR, The New York Times cut off ad exchanges and k... by semi-extrinsic on Wednesday January 16, 2019 @12:59PM (#18923145)
Oh they definitely do this. At least the traditional loyalty-card/coupon-enabled physical targeted ads do add enough random stuff that you find it non-creepy, after they had a few high-profile cases back in the day where they started targeted advertising of baby products to teenage girls, and parents got mad. The kicker was they turned out to frequently be real cases of teen pregnancies.
Re:After GDPR, The New York Times cut off ad exchanges and k... by noir_lord on Wednesday January 16, 2019 @03:12PM (#18924585)
I remember that, it was Target wasn't it and they inferred her pregnancy status because she started buying unscented deodorants and stopped buying sanitary products.

Funnily enough when I'm discussing the dangerous nature of large datasets in the hands of companies/bad actors (sometimes the one and the same...) and the "creepy" effects this is one of the examples I use, I've found that if you know a little about the person and couch the argument in a way they can personally respond to, they understand even if they don't know the first thing about technology generally.

EDIT: https://www.forbes.com/sites/kashmirhill/2012/02/16/how-targ... for anyone who hasn't seen it.