Thus the tears of compunction which are born as a result of someone’s reaching the state of purity and dispassion lead him to the perfection of the love of God. The sign that a person has reached the love of God is his ability to shed tears every time when he remembers God:
Question: And whence does a man know that his has attained to the perfect love of God? Answer: When the recollection of God is stirred in his mind, straightway his heart is kindled by the love of Him and his eyes pour forth abundant tears. For love is wont to ignite tears by the recollection of beloved ones. A man who is in this state will never be found destitute of tears, because that which brings him to the recollection of God is never absent from him; wherefore even in sleep he converses with God. For love is wont to cause such things.[11]
Isaac often says that tears of compunction should accompany prayer. Tears during prayer are, according to him, a sign that a person’s repentance has been accepted by God.[12] When the gift of tears is granted to a person during prayer, the delight of these tears should not be counted as idleness.[13] A multitude of tears is born to a person in the life of stillness, ‘sometimes with pain, sometimes with amazement; for the heart humbles herself and becomes like a tiny babe, and as soon as she begins to pray, tears flow forth in advance of her prayer’.[14] According to Isaac’s testimony, tears during prayer were experienced by the majority of good monks of his time: ‘(A monk) may receive the gift of tears during the office - something which the majority of right-minded brethren experience - tears which so compel that brother with their quantity that he is unable to complete the office, even though he struggles greatly to do so: instead, he has to abandon the office because of abundant weeping…’[15]
We see that Isaac does not regard tears as an extraordinary gift, as a special charisma, of which only very few are counted worthy. On the contrary, he considers that the experience of tears is necessary for every Christian, not necessarily a monk.
Isaac does not always distinguish between the bitter tears of repentance and the sweet tears of compunction. Rather, two types of tears are the two sides of one medal, two aspects of one and the same experience. The tears of compunction, which are born from mystical insights, from the love of God and from deep humility, are joyful tears. At the same time they are accompanied by repentance, by the awareness of one’s own sinfulness, by ‘burning suffering’ and a contrite heart.
orthodoxia.org/hilarion/articles/mystisaac/iscont.htm
ST ISAAC OF NINEVEH AND SYRIAN MYSTICISM
Lectures at the Divinity Faculty of the University of Cambridge. Spring 1999