That is weird and would definitely be outside my comfort zone. I did cry at work once when reporting sexual harassment, but I have never seen my supervisor cry.
I did have a problem a while back when my boss was sending criers to me because he thought I handled them well and they made him uncomfortable. I handled them by addressing why they were crying (feeling overwhelmed or upset about returning from maternity leave) and ignoring the emotional aspect. I told him to suck it up and handle them himself.
I stand and rejoice every time I see a woman ride by on a wheel...the picture of free, untrammelled womanhood--Susan B. Anthony