Quote from “Effective Pastoral Counseling” by Gary Collins (Manila, Philippines: OMF Publishers, 1984):
We have a cause for happiness but we must never get the idea that it is unchristian or unspiritual for people to be unhappy at times. Periodic discouragement is a part of life and although believers can always be glad for their relationship with Christ and for their awareness of His sovereignty, there is nothing in the Bible to imply that we should always be grinning with happiness and bubbling over with exuberance. On the contrary, there are times when a Christian should weep. (p. 97)
Collins goes on to quote John R. W. Stott regarding two groups of situations where weeping is appropriate. The two are:
Tears of Nature — This is the classic human response to trials, trauma, and loss. It is part of the natural grieving process.
Tears of Grace — This is more theological, perhaps — the healthy Christian response to living in a fallen world immersed in sin and suffering. ( You may note that tears of Nature and of Grace overlap considerably… perhaps too much to be separated.)
Collins then adds a quote from Stott on page 98
The fundamental error underlying our modern tearlessness is a misunderstanding of God’s plan of salvation, a false assumption that His saving work is finished, that its benefits may be enjoyed completely, and that there is no need for any more sickness, suffering, or sin, which are the causes of sorrow. … The eyes that do not weep are blind eyes — eyes closed to the facts of sin and of suffering in ourselves and in the rest of humanity.J.R. W. Stott, “When Should a Christian Weep?” Christianity Today. Vol. 14, November 7, 1989, p. 3-5.