A nice observation for you ​ did any tears fall from his eyes? If so did he allow them to fall? Did you see a tear even if only briefly. Can't really answer your question given that I am male but I have talked about crying with a woman. Both in term of my tears and her tears.

A friend of mine is very open about the fact that he cries (about normal human stuff, not just the stuff that is Socially Acceptable for Manly Men to cry about, ie dead dads or the team making the playoffs). He'll be like 'oh, I'd need to watch that movie alone, I'd just cry the whole movie long', or 'at the time I was having a really tough go of it emotionally, I'd be hiding in the bathroom crying'. And he's a friend I can go to for moral support and advice on how to deal when I'm crying and can't stop, cause i know he's been there.
 

Wow, you are quite the lucky one. It is merely a dream of mine to meet a guy that open about his emotions to me.