> That to me is by definition judgmental.

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.