Most depictions of Our Lady of Sorrows highlights the agonizing pain that Mary suffered when witnessing her Son's passion.
At times her tears can comfort us when we are crying, showing us that she too suffered much in this world.
However, sometimes when we suffer it is more beneficial to see Mary's smile, knowing that she is with us and desires to comfort us in our pain.
Seeking Mary's smile
Pope Benedict XVI meditates on the desire to see Mary's smile in a homily he gave on the memorial of Our Lady of Sorrows in 2008:
The psalmist, seeing from afar this maternal bond which unites the Mother of Christ with the people of faith, prophesies regarding the Virgin Mary that “the richest of the people … will seek your smile” (Ps 44:13). In this way, prompted by the inspired word of Scripture, Christians have always sought the smile of Our Lady, this smile which medieval artists were able to represent with such marvellous skill and to show to advantage. This smile of Mary is for all; but it is directed quite particularly to those who suffer, so that they can find comfort and solace therein.
He explains that looking for Mary's smile is not something sentimental, but is something we should all desire in the midst of our suffering:
To seek Mary’s smile is not an act of devotional or outmoded sentimentality, but rather the proper expression of the living and profoundly human relationship which binds us to her whom Christ gave us as our Mother.
Pope Benedict XVI particularly mentions how the Magnificat can be a channel for this smile:
To wish to contemplate this smile of the Virgin does not mean letting oneself be led by an uncontrolled imagination. Scripture itself discloses it to us through the lips of Mary when she sings the Magnificat: “My soul glorifies the Lord, my spirit exults in God my Saviour” (Lk 1:46-47). When the Virgin Mary gives thanks to the Lord, she calls us to witness. Mary shares, as if by anticipation, with us, her future children, the joy that dwells in her heart, so that it can become ours. Every time we recite the Magnificat, we become witnesses of her smile.
When our own life is shattered, we can rest comfortably in the arms of the Virgin Mary and look up at her and see her smile comforting us in our time of sorrow.