John Gill's Bible Commentary Ver. 5. Answer a fool according to his folly , etc.] The Targum is, “but speak with a fool in thy wisdom;” and the Syriac version, “yea, speak with a fool according to thy wisdom;” which would at once remove the seeming contradiction in these words to the former, but then they are not a true version; indeed it is right, and must be the sense, that when a fool is answered, as it is sometimes necessary he should, that it be done in wisdom, and so as to expose his folly; he is to be answered and not answered according to different times, places, and circumstances, and manner of answering; he is to be answered when there is any hope of doing him good, or of doing good to others; or of preventing ill impressions being made upon others by what he has said; when the glory of God, the good of the church, and the cause of truth, require it; and when he would otherwise glory and triumph, as if his words or works were unanswerable, as follow; lest he be wise in his own conceit ; which fools are apt to be, and the rather when no answer is given them; imagining it arises from the strength of their arguments, and their nervous way of reasoning, when it is rather from a neglect and contempt of them.
Matthew Henry Commentary
Verses 4, 5 - We are to fit our remarks to the man, and address them to his conscience, so as may best end the debate.
Original Hebrew ענה6030 כסיל3684 כאולתו200 פן6435 יהיה1961 חכם2450 בעיניו׃5869