I don't know if this will help or not, but if you need to cry more, I think you should do so. If you need help getting this/these sad feelings out, so maybe listen to very sad songs, all you can think of. My fave (but not really) sad song is "Old Shep" (I think that's the name) by Elvis Presley. Listen to the sad songs, lament why you feel sad and cry, cry, cry. Try Pandora.com where you can make your own radio station and request songs and singers, musicians. Think of the times your heart was broken, painful memories, etc. Despair is hard, but it you can perhaps get 'cried out,' maybe you will end up not in despair. Holding in feelings we are afraid of or dread is very harmful. Do not despair, there is/are always hope and love and friendship and beautiful things in this world.
For myself, I cannot cry because of the prescriptions I am taking. Haven't been able to cry for years with one exception: when I've had to put down one of my beloved cats. But not even when my mother died could I cry.
I very much wish I could cry. I know it would help me to feel better.
This is just a suggestion, but may be worth trying, I don't think it can't hurt if you know what your intention is...
PrairieCat