One way of praying the Rosary involves meditating first on how the mystery relates to Mary's love for Jesus, and then on what Mary's love teaches about our own love for Him.
Obviously, this requires a certain amount of imagination. We project onto our meditations our own ideas of what Mary may (or "would have" or "must have") thought, felt, and done.
But it may also involve some psychological projection onto our own thoughts and feelings. With the finding of Jesus in the Temple, for example, whatever reflection I have has to work around the facts that a) I am not nor have I ever been Jesus' mother; and b) I knew all along how the three-day search would turn out.
Similarly, the sight of Jesus carrying His cross "must have" related to Mary's love for Him in a way that it cannot relate to mine. I do the pop Ignatian thing of imagining myself in the scene -- especially this week -- and am sometimes given the grace of being profoundly affected.
But it can't stop there. I am not living in First Century Palestine. I am not, in fact, standing next to the Blessed Mother as she reaches out to her condemned Son. I am actually driving in a car, or kneeling in a church, or sitting in a comfortable chair in a quiet room.
If I get my emotions and my reason properly attuned to the sorrow of Jesus' passion, if I tell Him, "I have placed myself along the Way of Sorrows, and I offer to You as You pass my grief and my support," ... what good does that do Him?
Yes, I've heard people say that they feel, or at least like to think, that their own prayers today in some way helped support Jesus in His suffering. But what did Jesus say to those people who actually did express their grief to Him as He passed?
What Mary's love for her suffering Son teaches us is love for her suffering Son, not as He suffered in Jerusalem in the days of Caiaphas the high priest, but as He suffers today.
When the Son of Man returns in glory and says,
I was hungry, thirsty, a stranger, naked, ill, in prison... Whatever you did for the least of My brothers, you did for Me.
He will not be speaking in a merely juridical sense. If an ordinary king said this, he would mean that, for purposes of reward and punishment, actions toward his brothers shall be treated as if they were actions toward himself. I don't think Jesus is proposing such a legal fiction here; I think that what is done for His brothers is done, really and for true, for Him.
The hungry, the thirsty, the naked, the ill, the imprisoned: these are the people whom we must love as Mary loved Jesus. If we try to love Jesus now the same way Mary did then, we'll only be fooling ourselves -- blinding ourselves, even, to the mission He has given us. "Men of Galilee, why are you standing there looking at the sky?"
This is even true of Mary herself. We think of Jesus' word, "Woman, behold thy son," as proof of His loving care for His mother, who would otherwise be alone in the world, and it is that. But I'd suggest that it is also an instruction to her, that she must now reach out to others with that very love she had for Jesus; given at a moment when all she "would have" wanted to do is look to her Son, it may even have caused her some pain.
But no one, not even the Blessed Virgin, gets to set their own terms as a disciple of Christ. We may wish to remain at the foot of the Cross, our eyes never leaving Jesus. But that grace was not even given to those who physically were at the foot of the Cross. We must take all that we gain from the Cross to others; that's the only way for us to love Him now as Mary did then.