I don't know if it's entirely a gender difference. My male T is really good at this sort of stuff - certainly a lot better than I am and definitely better than previous (female) T.
Honestly it makes sense that your T struggles with this kind of stuff given the confusing push-pull-ish boundary instructions he gave you regarding the emailing...
The comment about men being dismissive of those who hurt them screams 'unresolved issue' to me. I don't think men are any more dismissive of being hurt than women, they just maybe deal with it differently.