Thomas Watson, in The Godly Man’s Picture Drawn with a Scriptural Pencil (Edinburgh, 1999) has a great little section on repentance and weeping in this “Puritan Paperback” that describes the characteristics of a godly person (p 56-58).
Why does a godly person weep?
1) He weeps for indwelling sin, the law in his members (Rom 7.23). A regenerate person grieves that he carries that about him which is enmity to God; his heart is like a wide sea in which there is enmity to God…
2) A godly man weeps for clinging corruption. Though a child of God forsakes his sin, yet sin will not forsake him. So though the dominion of sin is taken away, yet its life is prolonged for a season; and while sin lives, it molests.
3) A child of God weeps that he is sometimes overcome by the prevalence of corruption. The evil which I would not do, that I do (Rom 7.19). It cannot but grieve a regenerate person to think he should be so foolish as, after he has felt the smart of sin, still to put this fire in his bosom again.
4) A godly heart grieves that he can be no more holy. It troubles him that he shoots so short of the rule and standard which God has set.
5) A godly man sometimes weeps out of the sense of God’s love. Gracious hearts, which are golden hearts, are the soonest melted into tears by the fire of God’s love.
6) A godly person weeps because the sins he commits are in some sense worse than the sins of other men…Because he acts contrary to his own principles. The sins of God’s people put black spots on the face of religion.
This is a brief summary of a great section of an outstanding book on true piety. In the application section of this teaching on tears of repentance, Watson summarizes: “Repenting tears are precious. God puts them in his bottle (Ps 56.8). Let us give Christ the water of our tears and he will give us the wine of his blood.”