Psalm 88 is the exception that proves the biblical pattern: it is the one psalm that ends in darkness with no resolution, no turn toward praise, no morning after the weeping. "Darkness is my closest friend." It was included in the canon anyway — which means God permits prayers that end in unresolved complaint. The psalmist does not need to arrive at a theologically satisfying conclusion before his cry is valid.
Job 23:3 is the cry of a man who cannot find God to argue his case: "Oh that I knew where I might find him!" He has not stopped wanting to talk to God — he is desperate for the encounter. This is not unbelief; it is intense, frustrated faith. Lamentations 3:33 provides the theological anchor under the disappointment: "he doth not afflict willingly nor grieve the children of men." The suffering is not his preference. It is not evidence that he has turned against you.
Commentary is from a charismatic Protestant perspective, drawing on KJV text and public-domain sources including Spurgeon, Andrew Murray, and Matthew Henry.