It is suggested when praying the chaplet to say an Act of Contrition at the very beginning, recognizing the role our sins had in Our Lady’s sufferings.
One method that helps facilitate the meditation on Mary’s sorrows is to announce each sorrow before praying the seven Hail Marys. Here is the text given by the Church in the 1910 version of the Raccolta:
With this confidence in my heart, I meditate on the First Sorrow, when Mary, Virgin Mother of my GOD, presented JESUS her only Son in the Temple, laid Him in the arms of holy and aged Simeon, and heard his prophetic word, “The sword of grief shall pierce thy soul,” foretelling thereby the Passion and Death of her Son JESUS.
The Second Sorrow of the Blessed Virgin was when she was obliged to fly into Egypt by reason of the persecution of cruel Herod, who impiously sought to slay her well beloved Son.
The Third Sorrow of the Blessed Virgin was when, after having gone up to Jerusalem at the Paschal Feast with Joseph her spouse and JESUS her beloved Son, she lost Him on the way back to her poor house, and for three days bewailed the loss of her only Love.
The Fourth Sorrow of the Blessed Virgin was when she met her dear Son JESUS carrying to Mount Calvary on his tender shoulders the heavy Cross whereon He was to be crucified for our salvation.
The Fifth Sorrow of the Blessed Virgin was when she saw her Son JESUS raised upon the hard tree of the Cross, and blood flowing from every part of his sacred Body, and then beheld Him die after three hours agony.
The Sixth Sorrow of the Blessed Virgin was when she saw the lance pierce the sacred Side of JESUS, her beloved Son, the nails withdrawn, and his holy Body laid in her purest bosom.
The Seventh and last Sorrow of the Blessed Virgin, Queen and Advocate of us, her servants, miserable sinners, was when she saw the Holy Body of her Son buried in the grave.
V: Pray for us, Virgin most sorrowful.
R: That we may be made worthy of the promises of CHRIST.
Let us pray.
GRANT, we beseech Thee, O LORD JESUS CHRIST, that the most blessed Virgin Mary, thy Mother, may intercede for us before the throne of thy mercy, now and at the hour of our death, whose most holy soul was transfixed with the sword of sorrow in the hour of thine own Passion. Through Thee, JESUS CHRIST, SAVIOR of the world, who lives and reigns with the Father and the Holy Spirit, forever and ever. Amen.
The Chaplet of the Seven Sorrows is a beautiful tradition in the Church and allows a soul to walk the via matris, following Mary who kept all of these sorrows in her heart.