Fra Angelico’s painting, The Conversion of St. Augustine, offers a great insight into the spirituality of the Doctor of Grace. At the forefront of the painting, commanding the immediate attention of the viewer, is the figure of St. Augustine sitting and weeping. The painting portrays the moment of St. Augustine’s conversion as it is described in his Confessions (book VIII, chapter 12).

In the garden of his friend’s house in Milan, after long struggles with “old attachments” that kept him from embracing the life of continence, Augustine gave way to the “storm” of tears that had been welling up inside of him, expressing his great remorse for his sinfulness, which proved to be invincible to his own strength. He wept because he felt he was the “captive” of his “sins,” and while crying, he kept repeating, “How long shall I go on saying ‘tomorrow, tomorrow’? Why not now? Why not make an end of my ugly sins at this moment?”

Augustine’s tears signify a moment of recognition as well as an articulation of “inexpressible groanings,” of sentiments that are too profound to be expressed in human words (Rm 8:26). He recognizes his ineptitude and powerlessness when dealing with the consequences of his wounded nature. This recognition makes him look for a different source of strength through which he can overcome his weaknesses. He lifts his gaze to God and discovers the mystery of grace, which alone has the power to change the hardest of hearts and heal the most festering of wounds. Tears are the beginning of the road to holiness for this hopeless sinner.

These “inexpressible groanings” communicate to God the soul’s deepest yearnings for salvation. On the one hand, these yearnings are mysterious and difficult for us to put into words. They are often tucked away or covered with the meaningless noise and clamour of our transient and worldly cares. On the other hand, the Father hears these yearnings from afar. He catches “sight” of them while they are “still a long way off” and sends the Holy Spirit, Who “comes to the aid of our weakness” by translating them into a prayer consisting of “inexpressible groanings,” which communicate to the Father our deep-seated longing for heaven (Lk 15:20, Rm 8:26). The visible sign of this communication is torrential tears, tears of repentance that wash away our past and urge us on to a new beginning.

St. Augustine’s tears were not without important parallels. To the left of Fra Angelico’s painting stands the figure of a man whose posture also denotes an emotional moment that is related to the one experienced by the main character. This figure is Alypius. At the same time of Augustine’s conversion, Alypius also experiences the voice of God in his life through a scriptural passage that he reads in the Letter to the Romans. When they both disclose to each other their desire to commit their lives to God and take up the life of celibacy, they go to Augustine’s mother, St. Monica, and inform her of their decision. In turn, Monica is overjoyed at this news because she sees her son’s commitment to the celibate life as God’s generous response to her many “prayerful tears and plaintive lamentations.”

St. Monica is very closely connected to her son’s conversion. She spent 17 years shedding tears over his waywardness, begging God for his soul. When her son embraced the Manichean heresy,  she asked a Catholic bishop to speak to him and refute his errors. The bishop told her it was unwise to have that conversation with her son because he was “unripe for instructions,” and that, in time, he would discover the truth simply by reading the Manicheans’ books. This answer would not pacify the mother. She was relentless in her visits to the bishop, incessant with her tears for her son’s conversion. Finally, losing his patience, the bishop said to her, “Leave me and go in peace. It cannot be that the son of these tears should be lost.” He was correct; the son of tears discovered the Truth and offered his life to Him.

image: The Conversion of St. Augustine by Fra Angelico

Editor’s note: This article originally appeared on Dominicana and is reprinted here with kind permission.