The Theotokos of Vladimir is an icon written (icons are technically 'written' not 'painted') in the year 1130 in Constantinople and is currently in the Tretyakov Gallery in Moscow. Theotokos means 'bearer of God,' and there are series of Theotokos icons, of which our present study is a part, called the Eleusa icons. Eleusa means tenderness. And so this image is sometimes referred to as 'The Virgin of Tenderness.'
Mary is holding Jesus delicately, while staring, if you notice, directly at us. Mary wants a relationship with us. We will be fulfilled if we do. It is also as if Mary wants us to have the same desire for her as her Son does. There is a lot of significance in those eyes. Mary's tender and penetrating eyes are always upon us. This is a beautiful thing. We never want a mother and a lady's gaze to drift elsewhere. We are possessive of the feminine attention. Mary satisfies our need.
The infant appears as if he is trying to climb Mary, to get as close to her as possible. A sandal of Jesus has even fallen off (see the right foot) in his haste to fly unto his Mother. Mary is cooperative with this effort. Her left hand seems to be pushing Jesus upwards. You will also notice Jesus' right hand on the face of Mary. He has wrapped his arm around her neck--another sign of affection. Our Lord embraces Mary. The faces of mother and son are touching as well. Great intimacy is present in that physical connection. And Jesus, of course, is looking directly into the eyes of his mother.
If there are times in our life we do not believe Jesus is looking at us, chances are he is looking at us through the eyes of his tender Mother.