Crying's a funny one for me. I really wear my heart on my sleeve and am a very demonstrative and emotional person at times and yet I rarely cry. Probably no more than half a dozen times in my adult life. I certainly don't see men crying as a weakness; quite the opposite. I should cry more than I do really, but these things can't be forced.
Last time was in 2012. Over a girl, as has pretty much all those other half dozen occasions. Partly out of self-pity and remorse, but also out of genuine sadness at love lost. I always bounce back though. I think that's probably my greatest quality.
There is certainly something therapeutic about crying: est quaedam flere voluptas.