This contributes to my distress in dealing with crying people, because I know that if I were in their place, the same actions could make my mood better or worse depending on something the other person couldn't be expected to know about.

Yes! I definitely know that feeling. There are some times where people offering hugs is exactly what I need and there are times where hugs are exactly the opposite of what I need. This is kind of why I kind of think asking people stuff and requesting stuff are really the best policies, even if they don't feel socially sensitive-looking enough sometimes and can be subverted by manipulative people.

I think that men are often at a loss dealing with crying people for this reason.

I think I understand? It's like this unthinkable thing you can't imagine happening to you so you don't know what to do when it's happening to someone else. But thinking about unthinkable things is useful and good for your brain! (One day, you might be around some onions or something.) I still think that specific "distress" reaction not useful, and maybe can be helped by working out a specific procedure and sticking to it like a robot even when you feel weird.

I've been in these absurd situations where a guy gets so upset that I'm crying, that I have to comfort him even though he did the thing that made me cry in the first place. I've also had people assume not crying about something means it's not important. I think it would be nice to demystify crying as an imperfect physical process that doesn't always correlate with importance, clarity, sensitivity, etc.