The overwhelming pain of witnessing the destruction of one's surroundings is channeled entirely through the eyes. Sight itself becomes a source of deep suffering and agony. In this state of personal and national mourning, tears are not simply a reaction to loss. They actively work upon the soul of the mourner, leaving a profound impact. The primary approach among commentators is that this constant crying causes direct harm, degrading and dirtying the face with endless sorrow. Others view the weeping eye through the imagery of the grape harvest. Just as a few solitary grapes remain on the vine after the harvest is gathered, the mourner watches relatives face death and exile, feeling that their weeping eye is left completely alone, crying for all those who are gone [אבן עזרא, ביאור שטיינזלץ].
The source of this intense grief is understood in several ways. Some attribute these feelings directly to the prophet Jeremiah. Coming from a distinguished family of priests chosen for God's service, he feels a unique burden, believing his family must weep and suffer even more than the other families of the city [רש״י, צאינה וראינה]. This sense of total isolation and absolute loss is also linked to later historical tragedies, such as the destruction of the city of Beitar. The city once held hundreds of schools with thousands of young students. When the enemies arrived, they wrapped the children in Torah scrolls and burned them. The sole survivor of that massacre expressed the shattered spirit of being the last remaining remnant [תורה תמימה]. It is the crushing pain of an individual watching all their neighbors perish, their eyes filled with tears for everything done to the people of their city [ביאור שטיינזלץ].
A completely different perspective identifies the surrounding people not as the victims, but as the enemy nations. From this viewpoint, the deepest psychological pain a person can endure is watching an enemy succeed. The mourner's own eyes cause him agony specifically because he is forced to witness the prosperity and well-being of these foreign nations [פלגי מים]. Yet, tears also possess a powerful healing quality. Even though God sent these surrounding nations to bring suffering upon Israel in order to correct them, the congregation of Israel realizes that her own flowing tears do more to heal and mend her soul than any affliction caused by her enemies, for the gates of tears are never closed [אלשיך]. Finally, the suffering experienced through the eyes is also seen as a direct consequence of past actions. The darkness and pain striking the mourner's vision are the result of the sins of the women of the city, who once walked with arrogance and looked at others with sinful intent. The injury to the eye is a direct response to those who sinned with their gaze [אלון בכות].