The topic of mourning is one that is often deliberately avoided. This is perhaps a result of the incessant messaging in our culture that we ought to avoid death and live for the now. This creates not least a perspective that everything is all right. Even within the communities of the faithful it is difficult to avoid being formed by this mentality and the result is often churches that that express one side of the human experience. Embracing the reality of life requires that we consider the fullness of the human experience, of which mourning is a vital component.
Below are some reflections borrowed from HERE
BLESSED are those who mourn, for they will be comforted.
"BLESSED are those who mourn" is, paradoxically, a more necessary message than "Rejoice in the Lord always," because there can be no true rejoicing until we have stopped running away from mourning.
Simon Tugwell, The Beatitudes
[W]E WILL NEVER experience the angel of comfort until we can enter into the mourning. … The admission of what is deepest within us can be done only with an angel of comfort. This angel comes to us in the appearance of a total stranger or an absolute friend.
Michael H. Crosby, Spirituality of the Beatitudes
[MOURNING] cannot be limited exclusively to expressing sorrow for one’s sin … or grief surrounding death. … Rather, "those who mourn" has the more comprehensive sense of Isaiah 61:2-3, an inclusive grief that refers to the disenfranchised, contrite, and bereaved. It is an expression of the intense sense of loss, helplessness, and despair.
Robert A. Guelich, The Sermon on the Mount
THE DISCIPLES bear the suffering laid on them only by the power of him who bears all suffering on the Cross. As bearers of suffering, they stand in communion with the crucified. They stand as strangers in the power of him who was so alien to the world that it crucified him. This is their comfort, or rather, he is their comfort, their comforter. … This alien community is comforted by the Cross.
Dietrich Bonhoeffer, Discipleship
IN THIS BEATITUDE, Jesus praises … those who can enter into solidarity with the pain of the world and not try to extract themselves from it.
Richard Rohr with John Bookser Feister, Jesus’ Plan for a New World
HE CALLS BLESSED even those who mourn. Their sorrow is of a special kind. He did not designate them simply as sad but as intensely grieving. Therefore, he did not say "they that sorrow" but "they that mourn."
John Chrysostom, "Homily 15.3"
IT IS NOT ENOUGH for us … within the arena of the world’s pain merely to know of a God who sympathizes. It is not even enough to know of a God who heals. We need to know of and be connected with a God who experiences with us, for us, each grief, each wound. We need to be bonded with a God who has had nails in the hands and a spear in the heart!
Flora Slosson Wuellner, Weavings
EVERY SUFFERING can be blessed because it hollows out a place in us for God and his comfort, which is infinite joy.
Peter Kreeft, Back to Virtue
IT IS impossible for one to live without tears who considers things exactly as they are.
Gregory of Nyssa, De Beatitudine