As such it wasn't "reading other people's messages". That's according to the OKC founders description of what they did, pre-acquisition. Since they were reasonably upfront about what they did, and since that functionality worked even for free users and they didn't aggressively push premium or gate the features, I believe they were being truthful. Furthermore, after the 2011 acquisition and when they stopped being active on OKC itself, there was a palpable degradation in site quality. (And post-2014, IAC went on to sell personal information about users' substance use etc. to insurers, to which users had never given informed consent).
So I think your date explained things badly and you picked up the wrong end of the stick. It's trivially easy to write a script that strips usernames and identifying information. And it's not too hard to distinguish "Hey baby" or "DTF?" from more meaningful messages. For the platform to do that with an intent to improving matches was strongly positive, not negative.
> For the platform to do that with an intent to improving matches was strongly positive, not negative.
Do you realize how much work that OkCupid has put into their product to make matching intentionally worse (through analysis!)? Take off your rose-tinted glasses!!
Edit: aaaand there's a new article about OkCupid giving facial recognition data to 3rd parties.