The point I was making in my initial reply was in response to the trivialization of what someone else cares about ("sad enough to cry over productivity software"). That to me is by definition judgmental.
I don't believe there is a universal list of things that is OK to care deeply enough to cry about. There are plenty of things you would cry about that I would not, but I can understand why you would care deeply about those things. Or maybe you are of the opinion that crying isn't allowed at all. Which is also an opinion.
My use of "judgmental" was to communicate that my intention was not to pass judgment on his worth as a person or his worthiness of respect as a person or professional in me providing honest feedback about his behavior.
> I don't believe there is a universal list of things that is OK to care deeply enough to cry about.
It's not about prescribing when it's OK to cry or trivializing what he's sad about, it's about deviations from average behavior. The vast majority of emotionally well-adjusted men usually only cry at the death of a loved one or during a divorce or serious break-up. Here's data on that: https://yougov.com/en-us/articles/51961-the-who-what-where-w... To find yourself crying in a situation different from those situations should raise a red flag. Yes it may be the case that it's not a sign of anything serious but given the rarity of the situation, it's reasonable to suspect there may be something else at play, e.g. low testosterone.
26% have cried in the last week
39% have cried in the last month
64% have cried in the last year