*shrugs*
To me, it all depends on why someone (whether man or woman) is crying and the motivation behind it. The last relationship I had was with a man who regularly broke out into blubbering sobs, usually when talking about his children. No doubt, he'd had a rough life. He was raising his two youngest kids on his own because the mother had passed away (she had a seizure and drowned in the bathtub, and he was the one to come home and find her there.)
However, his crying was usually done in order to manipulate people. I remember being very, very angry one Christmas season when he proudly told me someone had given him $100, and one of the reasons was because he was using MY life (telling people the background of my adoption) along with his own in order to sway people's sympathies. I was LIVID. Because the part he doesn't tell people is that he doesn't work and uses any money coming in for cigarettes and alcohol, not feeding or clothing his children (he relies on family and girlfriends to do that.)
On the other hand, I have sat with men who have gone through terrible things and shed tears while relating what happened to them or others they were close to. I see absolutely nothing wrong or shameful about that.
One of my favorite characters ever in the Bible is Joseph, the son of Jacob. What people forget is that he was thrown into prison for several years. Having talked to modern men who have been prison for many years, I am always amazed that God kept Joseph's heart from becoming bitter, because I can only imagine what kinds of horrors he probably went through that no one wants to think about. Several years ago I visited a prison in Europe that supposedly once held Peter and Paul. It was basically a cramped hole dug into the ground (even I had to duck, and I'm only about 5 feet tall.) It was absolutely pitch black, with no safety from rodents, disease, complete darkness... or other inmates. And seeing as Joseph was in a prison many, many decades before this, I can hardly fathom how much worse the prison he was in probably was.
And yet, his heart was still pliable enough that when he recognized his brothers standing before him--more than once--the Bible says that he was so overcome that he had to hurry to find a place to weep, and that he wept so loudly that the Egyptians heard him.
Joseph was every bit a man's man in every way, and yet there were times he expressed his emotions through tears, even after his father died and his brothers revealed that they were still terrified of him.
We are all given different personalities for a reason. I myself am not much of a crier (I do cry, but very rarely), but I believe there are times and places when, if that's part of who God made you to be, crying is more than appropriate, no matter what gender you are.