I don't think the sticky point is whether or not we should be experimenting with people to find what works and what doesn't. It's about respecting users as humans and not simply data points. How does OkCupid know that conversations "went deeper" or how often emails and numbers were exchanged? Were the participants aware of that level of scrutiny or is that tucked away in the ToS? Most people I know aren't even comfortable talking about their OkCupid, they use it as a means to an end and place trust in the service to be discrete. Do these experiments fall in line with user expectations?
I'm not saying you have to find these experiments upsetting just that when people are upset it tends to be about treating users like honorable guests and not about whether or not we should be allowed to tinker with services to find the right solution.
For the emails and numbers, they can probably search for those in the messages quite effectively without many false-positives.
I'm all for the expectations of privacy, but if you type something into a search box on a website owned by somebody else, well, you get what you pay for.
Sure, my comment wasn't to say they're doing anything nefarious. I'm actually not taking a position here either way. I'm just pointing out that people aren't upset that services use data to improve their services which seems to be the tone and premise of OkCupid's post.
I'm not saying you have to find these experiments upsetting just that when people are upset it tends to be about treating users like honorable guests and not about whether or not we should be allowed to tinker with services to find the right solution.