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St. Gabriel and All Angels

I believe that the suppression of emotion is one of the main culprits is keeping our inherent spiritual nature root-bound. By now it is commonplace to know about the medical and health benefits of "a good cry", but other lingering social conventions (and even spiritual teachings!) denigrate the natural feeling of sadness and the shedding of tears. (see: Health Benefits of Tears)

Of course most of us would prefer to feel joy, but denying, suppressing, or avoiding sad feelings when they naturally arise is a sure way to prolong the lessons and healing that stand before us. Rather than assuming an attitude of feeling joyful when healing is needed first, wisdom suggests that we find a way to accept the cup that has come to us. But remember, while we must do our own healing, we need not do it alone.

Some of the most difficult tears to face come when life presents us with the recognition of our own mistakes and failures. Not merely failing to earn money or gain respect, but those mistakes we make which hurt those we love.

And how counter-intuitive it can be that the one who created us is the most ready to overlook and forgive those things which we are least willing to forgive in ourselves. However comforting and easy that is to accept intellectually, the experience of redemption in the eyes of our God takes a genuine spiritual transformation. Mystics and lovers of God have always known that, and known the benefit of tears in the process.

Here is a wonderful reference on the recognition of the place of tears in the spiritual life:

The Gift of Tears
In The Ladder of Divine Ascent, Bishop Kallisto Ware believes that John Climacus discussed three levels of tears:

1. Contranormal tears which arise when our will is thwarted, for example tears of anger, jealousy, or frustration
   
2. Normal tears which arise in response to emotional and physical suffering, whether such suffering is experienced by ourselves or by others with whom we feel sympathy. Examples are tears of grief, pain, or compassion. These tears seem to contribute to our healing.
   
3. Supranormal tears are what mystics are referring to when they speak of the gift of tears. In the passage which follows, St. Isaac of Nineveh likens these tears to the tears wept at birth. The mystic who experiences such tears is being reborn into the age to come, and as such is experiencing a foretaste of heaven:
   

   The fruits of the inner man begin only with the shedding of tears. When you reach the place of tears, then know that your spirit has come out from the prison of this world and has set its foot upon the path that leads towards the new age. Your spirit begins at this moment to breathe the wonderful air which is there, and it starts to shed tears. The moment for the birth of the spiritual child is now at hand, and the travail of childbirth becomes intense. Grace, the common mother of us all, makes haste to give birth mystically to the soul, God's image, bringing it forth into the light of the age to come. And when the time for the birth has arrived, the intellect begins to sense something of the things of that other world -- as a faint perfume, or as the breath of life which a newborn child receives into its bodily frame. But we are not accustomed to such an experience and, finding it hard to endure, our body is suddenly overcome by a weeping mingled with joy.
   (Kallisto Ware adapting a passage from "Mystic Treatises by Isaac of Nineveh" ET A.J. Wensinck, p. 85, quoted by Ware on pp. 26-27 of The Ladder of Divine Ascent)

   Somewhere between normal and supranormal tears are the tears shed in mourning over one's sins. Like normal tears, these tears bring healing. However with reconciliation, tears of sorrow begin to mingle with tears of joy and take on a supranormal quality.