At the risk of being tautological, I think it's chilling because if he told the 10 girls he "doxed" about what he had done, I'm pretty confident a sizeable number of them would have the chills.

People don't like to feel like they're being taken advantage of, which would be a pretty common reaction to finding out someone had done all of this profiling on you to get you to go out with them.

It's not outright nefarious, because, what is he really doing that's different from a dating site filtering results by your criteria; except that these aren't people who have joined a dating site.

This sounds like the kind of thing Tim Ferris would recommend doing; asymmetrical information warfare in the battle of the sexes.