In all honesty, I don't think a man should cry easily. In other words, he should not cry as soon as the situation occurs. He has to at least bear some of the pain and at least put in an effort to not cry.
Why? I believe that when a man is allowed to cry in tough situations, it becomes a habit, and what you have is a man who does so much crying. Crying helps relieve pain, sure. However, a man has to have a better handle of his emotions because life goes on, and there are responsibilities that need to be met. I've done a bit of crying myself. And what I noticed about myself, is that when I'm crying, I have this pity party and it's all about "me me me" and I want others to feel sorry for me. Also, I stop my pursuit of my goals because I'm crying.
Crying has it's place and it's okay to cry, but crying should not be a characteristic a man is known for. He's gotta bear the pain, wipe his tears, be a soldier and handle business.