I am agreeing with some things already said regarding our boys, that they have these feelings, but don't show them. They repress them. In Ennis' case, despite the fact that he cried more than Jack in the film, I still think he has more repressed feelings than Jack. Though I can't really say why I feel this way...
The men I know best in my life are my stepdad and my father. My stepfather and father are as different as can be. My father is quiet, reserved, compleely unemotional. The only time I ever saw him cry was at his mother's funeral in 2001. And even then, it wasn't that tears were flowing; as far as I could tell they were still in his eyes. He was stiff and frozen.
My stepdad has never cried that I know of. When he's upset, he launches straight into anger. He's never violent, thank God, or I'd be terrified to be in the same room with him. But he shouts and swears. Sometimes I think he must be very repressed regarding his feelings in general because he will get upset over the STUPIDEST things! Like, for example, if he can't find some bananas or lunchmeat that was simply misplaced. When my mother points them out to him, he flips because he's been proven wrong. That's something that irks me altogether about him. Niether of us like to be proven wrong. When I know I am right, when disagreeing with him, we get into a shouting match that never ends! Thank God I have my own house now where I can go to get away from him, even if it is just next door. That's still a lot better than locking myself in my room for fear he would burst in.
I have an older brother, but he is very much like my father in that he doesn't really show his feelings either.
This might sound silly, but the only time I ever saw a man cry in "real life" would be at Skate Canada in 2005, when Johnny Weir sprained his ankle in the middle of his program, yet continued to skate. After he finished, he went to receive his marks and cried, but he did not show his face; he had his head down. You could hear him sobbing, that of course was from the physical pain, also perhaps the possibility that he might have to be out of competition for a while which might have jeopardized the Olympics...
But I digress. Anyway, that's really the only time I saw a man really "cry" in a real life circumstance.