When you are hurting and feel like crying, then cry. We have many things come into our lives that can cause us to want to cry. People hurt us, we have broken relationships, we have dreams and goals that fail. It can be any number of things. This goes for boys as well as girls, men as well as women. Boys and men tend to hold in their feelings more because of standards and upbringing that make them think it is not OK to express their feelings. This has been known to be unhealthy so let it out.
Crying will help you heal and God sees your tears and will dry your tears. Ask Him to help you get through whatever you are facing. Many times when you hold the crying in, you get angry and mean. Your feelings have to come out and when you hold them in they come out in inappropriate ways. That anger is taken out on others that have not even caused your pain. You will tend to hurt others because of your pain. You will hurt those that may be trying to help you through your situation.
When you cry, there will be others that understand how you feel. There are others that have experienced the same kind of hurt that you are going through. You will get past these hard times and it may be a while before things look brighter but it will get easier. You may be the one that gets to help the next person through their hard time. So go ahead and cry and you will regain your strength.