Yep, I agree. It all depends on the relationship as well. Yeah I never bring up the loss of someone a coworker has lost since I'm not really close to them. If they come out and say they have to attend a funeral or that someone they know passed away, then I'll give condolences. But other than that, I don't say anything. The way I see it, if you ask someone how they are and they say pretty good despite the obvious, then I take that as a sign that they prefer to keep it private which is totally understandable.

I'm the same way. In some cases, the only reason I found out a coworker lost someone is because they told someone else and that person spread it to others in an email or text. So I would think, well, maybe this person doesn't actually want me or others to know so I'm not going to say anything. Just because they told one person doesn't mean they wanted everyone else to know. Or that they only wanted a few people to know. It would be awkward to give condolences only for them to say, how did you know, I didn't tell you.