Question: Is it my imagination of does Proverbs 26:5 directly contradict Proverbs 26:4? What’s up with that?
Answer: Your imagination is playing tricks with you. Actually, many of our problems with interpreting Proverbs stem from our failure to understand what they are intended to communicate. There are three messages that wisdom in Scripture has for us:
(1) Wisdom is only acquired by those who want it bad enough to work for it (2:1-5). This means that all the meaning of what a proverb is saying is not always apparent on the surface. In fact, the way the proverbs are laid out (no apparent order, not topically arranged at all) means you have to really study them, meditate on them, to figure them out.
(2) Every issue has many sides to it (26:4,5). In the case of the proverbs you mention, responding to someone who is unreasonable is not a simple task. It requires wisdom to see that and not come with the same cookie-cutter approach to every problem.
(3) There are exceptions to some rules (10:4 and 13:23 plus the book of Job). Proverbs is not a book of promises, but wisdom and observation that tells us what is the norm in God’s world. It tells us how He normally works, but it points out, as in the proverbs cited, that He does not always observe our rules.
In the proverb you cite, there is a time to answer a fool according to his folly and a time not to. Jesus talked about not casting our pearls before swine (Matthew 7). This describes a situation where the receiver of truth despises truth and it is not worth telling it to him and may even be dangerous to. Paul is an example, however, of answering a fool according to his folly when in 2 Corinthians he brags and boasts of his “accomplishments” to the Corinthians because it was the only way they could receive him (11:16; 12:11). The wise person will learn when and how to respond to the fool in the best way possible, though even then he or she may not know which way was best until he or she got into it.