Proverbs 26:4,5 - Joseph Benson’s Commentary on the Old and New Testaments

Answer not a fool, &c. Answer a fool, &c. These contrary directions are easily reconciled, by considering the difference of persons, times, places, and other circumstances, and of the manner of answering. And such seemingly contradictory precepts are not only used by, but are esteemed elegant in other authors. Answer him not, when he is incorrigible, or when he is inflamed with wine, or with passion, &c., or when it is not necessary nor likely to do him good. Answer him, when he is capable of receiving good by it, or when it is necessary for the glory of God, for the discharge of a man's duty, or for the good of others. Answer not, &c., according to his folly So as to imitate his folly, in such passionate, or reproachful, or foolish speeches as he uses to thee; lest thou be like unto him Show thyself to be as great a fool as he is. Answer a fool according to his folly So as his folly needs and requires, convincing him strongly, reproving him sharply, and exposing him to just shame; lest he be wise in his own conceit Lest thy silence make him arrogant and presumptuous, as if his words were unanswerable.