Holy persons and holy fools in the Orthodox tradition will often weep, and spiritual counsel is often to be told to go and weep. As one of the desert fathers said, "Whoever wishes to be liberated from sins is liberated from them by shedding tears, and whoever wishes to acquire the virtues acquires them by shedding tears. Tears are the way which Scripture and our Fathers have handed down to us, saying 'Weep.' There is no other way but this."
Another saying from the Orthodox tradition: "A brother asked an old man, ‘What should I do?’ And the old man said to him, 'We ought always to weep.'"
What is the source and cause of our weeping? Two main answers come from the tradition. First, as noted above, there is sorrow for sin and through this sorrow we tame what is savage in our soul. But the deeper reason is love and compassion for the world. The famous description of the merciful heart from Isaac of Nineveh captures this well:
What is a merciful heart? It is a heart on fire for the whole of creation, for humanity, for the birds, for the animals, for demons, and for every created thing. And at the recollection and sight of them, the eyes of a merciful person pour forth tears in abundance. By the strong and vehement mercy that grips such a person’s heart, and by such great compassion, the heart is humbled and one cannot bear to hear or to see any injury or slight sorrow in any in creation.
The vision here is of a heart so exquisitely attuned to the suffering of the world that it weeps in compassionate response.
And so we weep. We weep for ourselves. We weep for the world. We weep for sin. We weep for love. And this weeping washes the heart clean. Weeping is the path to holiness.
Go and weep. There is no other way than this.