It can be both, like the annoying coworker who won't shut up about how much sex he had over the weekend, or the guy who raves about his favorite scotch at an AA meeting.

A correct observation does not shield it from being inappropriate or in poor taste.

I never minded OkCupid because it's sort of a game anyway. It's all online, and whether you meet someone there or not is up to you to tell OkCupid.

Uber is mining information about people's movements in the real world, which feels ickier.

Interesting. In the more socially-aware fora I'm familiar with, what's called "tone policing" or "tone trolling" is seen as a major faux pas, an aggressive act designed to shut people out of the conversation.