The miraculous icon of Theotokos Glykofilousa (Sweet Kissing) is placed on the marble shrine on the northeastern column of the Katholikon of the Philotheou Monastery. According to the tradition, it is one of the icons created by the Evangelist Luke himself. During the reign of the iconoclastic emperor Theophilos, the pious wife of the patrician and iconoclastic Simeon, known as Victoria, threw the icon into the sea to save it from desecration. The icon, after travelling for a long time, finally reached the Holy Monastery of Philotheou on Mount Athos. At the spot where it was found, a sacred spring is streaming today. The abbot of the monastery, to whom the miracle was foretold, went down to the sea with the rest of the monks on Saint Thomas' Sunday. In a solemn procession the icon was taken to the Katholikon.
To this day, many miracles have been performed. In 1713, the monk Ioannikios, who lit the candles of the church every day, approached the icon and said with reverence, "Why, my Lady, have you endowed all the other monasteries of Mount Athos with gifts, so that they have plenty of wheat, wine, oil, and other many goods, while this monastery suffers and struggles to buy the wheat it needs?" Another day he went again to light the candle, stood before the image and prayed. Tired as he was, he sat down in the pew opposite the icon and fell asleep.
Then the Mother of God appeared to him and said: "Why, my child John, do you often express dissatisfaction, saying that I take care of all the other monasteries except this one? Be assured that I take care of all your needs. However, I have decided to set things in this way, so that the monks of this place may be driven, not to earthly things, but to the search of their salvation. Stop bothering me with complaints, for I am the guardian of this monastery and you have nothing to worry about. Be concerned only about my temple and the salvation of your soul."
Hearing those words, John awoke in fear, fell on his knees before the holy icon and begged for forgiveness with tears in his eyes. Then he told to his brothers all that had happened.
The icon is also called “Orofilakissa”, “Pirofilakissa” and “Pirosotira”, which means “saviour from the fire”.
During the vigil celebrated on Thomas’ Sunday, a thanksgiving sequence is chanted, written by the elder Gerasimos Makriyannanitis, in remembrance of the help provided by the Virgin Mary during the liberation of Mount Athos from the Turkish invaders on the 13th of April 1830.
The icon of Theotokos Glykofilousa is the most important relic of the monastery. It is placed in a marble iconostasis, which, according to the inscription, was given to the monastery by Archimandrite Caesarion on March 25, 1851.
The figures are depicted according to a modified version of the iconostasis of the iconographic type of Theotokos Glykofilousa. The latter holds the Divine Infant in her arms, which she embraces with great tenderness, while her melancholy gaze turns towards the faithful. With His left hand Christ touches the face of His Blessed Mother, while with His right hand He touches her hand. In the two upper corners of the icon there are depicted the two Archangels, while at the edges of the frame there are the two hierarchs, Saint John Chrysostom and Saint Basil the Great.
This modified iconographic type of Theotokos Glykofilousa appears especially during the Palaiologan period. It is found in Kastoria, as well as in other regions of Macedonia. The oldest icon of this type, now placed in the Museum of Byzantine Art in Athens, dates from the 12th century and comes from an iconographer of Thessaloniki. This particular depiction of Jesus Christ in the arms of the Virgin Mary is a reference to the Passion and, in particular, to His burial and Resurrection.
Furthermore, the icon belongs to a special category of double-sided works, in which the reverse side is decorated with a representation of the Crucifixion. In this way, the doctrine of the incarnation of the Lord, through the Holy Mary, and the salvation of the human race, through the Divine Passion, is represented. In the depiction of the Crucifixion, the iconographer follows the established type. The crucified Christ is placed in the center, the Virgin Mary on the left and Saint John on the right, expressing their sorrow before the event.
Two angels are placed to the right and left at the top of the cross. We can also see the wall of the city of Jerusalem behind the figures of Mary and John. On the horizontal crossbars of the cross there are the inscriptions: "The Crucifixion. Jesus Christ. King of glory.".
The metal frame of the icon leaves the faces and some parts of the figures' bodies uncovered. The frame was donated by Archimandrite Caesar in 1840. There is also an inscription stating that it was created in Moscow in 1840 by the goldsmith Yupkin.