I remember when I first started looking into Orthodoxy, I thought the emphasis on weeping over sins to be a bit morbid.
But St. Symeon the New Theologian tells us the blessing that comes from this mourning, “Mourning has a twofold action: like water tears extinguish all the fire of passions and wash the soul clean of their foulness; and, again, through the presence of the Holy Spirit, it is like fire bringing life, warming the heart, and inciting it to love and desire God.”
This is why St. Philotheos of Sinai says, “I consider those fallen mourners more blessed than those who have not fallen and are not mourning over themselves; because as a result of their fall, they have risen by a sure resurrection.”