Is there a record of an association of prayer with pain?

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In Dark Night of the Soul, which is a Western work, John of the Cross talks about the extreme pain that the soul undergoes during prayer if/when God is removing its impurities.

Also, from the East, tears are considered to be an important part of prayer, and they represent the pain of the soul for its sins being poured out in tears of repentance.

As for experiencing physical pain, that appears to be a Western phenomena, the Eastern Church does not have record of anyone experiencing stigmata.

Here is the text for the common hymn for an asectic in the Eastern Church:

With the streams of your tears, you cultivated the barrenness of the desert; and by your sighing from the depths, you beared fruit a hundredfold in labours; and you became a luminary, shining with miracles upon the world, O (name of saint) our righteous Father/Mother. Intercede with Christ God that our souls be saved.

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In addition to the answer by RiverC, it is of note that the desert Fathers do have record of the devil inflicting physical hardship at time of prayer:

[Theodora] also said, “It is good to live in peace, for the wise person practices perpetual prayer. It is truly a great thing for a virgin or a monk to live in peace, especially for the younger ones. However, you should realize that as soon as you intend to live in peace, evil at once comes and weighs down your soul through faintheartedness and evil thoughts. It also attacks your body through sickness, debility, weakening of the knees, and all the members. It dissipates the strength of soul and body, so that one believes one is ill and no longer able to pray. But if we are watchful, all these temptations fall away. There was, in fact, a monk who was seized by cold and fever every time he began to pray, and he suffered from headaches, too. In this condition, he said to himself, ‘I am ill, and near to death, so now I will get up before I die and pray.’ By reasoning this way, he did violence to himself and prayed. When he had finished, the fever abated also. So, by reasoning in this way, the brother resisted and prayed, and was able to conquer his thoughts.” Wisdom of the Desert Fathers. Wilson-Hartgrove, Jonathan. Paraclete Press.

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