Blessed is the man who always fears the Lord, but he who hardens his heart falls into trouble. Proverbs 28:14

More than once in my life, my heart has fallen into hardness. Perhaps hurt, maybe anger, probably many things led to this. One of the consequences of this was that I felt far away from the Lord, cut off even. Having a soft heart also felt like a weakness to me. I rarely cry. Somewhere along the line, I lost the ability to do it. Tears are cleansing to the soul. It was when I was a teen, and I even remember where I was standing, when I decided that nobody would see me cry ever again. But that extended to being able to cry by myself, too. If the tears came, so did a myriad of words from my own mind telling me how stupid I looked, how I was just feeling sorry for myself, and that whatever it was, was not bad enough for tears. It got to the place when the only time I could cry was for death, and even then, the same little voice would tell me that I was just looking for sympathy. The "little voice" sounded an awful lot like my mom.
I don't think tears are a bad thing...it's just that it is difficult for me to cry myself. I can go months and months with nary a tear on my cheek. I don't think this is healthy, either spiritually or physically. It is WHEN I have been able to cry that I feel closest to the Lord, and more maleable to His Spirit.
So, let yourself cry. It keeps the hardness away. It keeps you human. It keeps you sensitive. There is no shame in tears. What hurts, hurts. Don't let anyone else tell you when you should cry, or for that matter, when you should be "over" something. Cry your eyes out. God hears your tears as they cleanse your soul, and soften the heart inside you.