Five Life-Changing Riddles From the Book of Proverbs

The book of Proverbs was recorded thousands of years ago, and yet those who spend time studying it will inevitably find that its wisdom is no worse for wear.

Many of the sayings in the book of Proverbs are straightforward. For instance, “He who passes by and meddles in a quarrel not his own is like one who takes a dog by the ears” (Proverbs 26:17).

Most of us don’t have to struggle to wrap our minds around the message there. Grabbing a dog by the ears is reckless, foolish—and totally avoidable. It’s an ill-advised decision that immediately makes your life worse and can’t be undone.

But some proverbs are a little more obscure, and not by accident. The book opens with a kind of foreword, explaining its own reason for existence. One of those reasons? “To understand a proverb and an enigma, the words of the wise and their riddles” (Proverbs 1:6, emphasis added).

Some of the wisdom of Proverbs is packaged into riddles—statements that might initially seem contradictory, confusing or otherwise illogical. They’re easy to dismiss or ignore, but these riddles are actually invitations for us to sit down and wrestle with the confusion—to pry back the seeming contradictions and walk away with a clearer perspective on how the world works.

There are a lot of riddles to wrestle with in the book of Proverbs. Here are five that can change your life.

1. Faithful wounds and deceitful kisses (Proverbs 27:6)

I might have an overly simplistic view of friendship, but one of the unspoken rules my friends and I all seem to share is that stabbing each other would put a significant damper on our relationship. And yet Proverbs 27:6 runs contrary to that rule:

“Faithful are the wounds of a friend, but the kisses of an enemy are deceitful.”

Faithful wounds? Faithful actions that cause pain and suffering? How can something like that come from a friend?

When I think of friendship, I think of people who enjoy each other’s company, who support and encourage each other. And yet in this proverb, it’s the enemy who best fits that description—at least outwardly—and it’s the friend who looks like an enemy.

There is a time to share hard, uncomfortable, even painful truths because of your love for a friend. And yet, what’s happening under the surface matters.

And there’s the riddle.

Sometimes, one friend needs to wound another because of friendship.

There is a time to share hard, uncomfortable, even painful truths because of your love for a friend. Hiding the truth when it could keep a friend from a serious mistake is a terrible way to show love.

By the same token, the people who tell us exactly what we want to hear—who shower us with praise, encouragement and validation—are not automatically those with our best interests at heart. An enemy can offer those things as easily as a friend, using them to gain and abuse our trust or hijack our attention.

So in this context, kisses and wounds are neither good nor bad in themselves. What makes them one or the other depends on who is providing them—and their motivation for doing so. Friends can hurt us, and enemies can praise us. Ignoring that truth can lead us into some truly dangerous places.

To learn about being a good friend, read “How to Be a Better Friend.”

2. Should I answer a fool or not? (Proverbs 26:4-5)

This is probably the quintessential example of confusing proverbs. The author appears to contradict himself in the span of just two sentences:

“Do not answer a fool according to his folly, lest you also be like him. Answer a fool according to his folly, lest he be wise in his own eyes” (Proverbs 26:4-5).

Well? Which is it? Answer a fool, or don’t answer a fool?

Another riddle.

In the book of Proverbs, fools are people who lack discernment and common sense—and they don’t just lack it, but forcefully and belligerently reject it. They refuse to learn, refuse to even hear.

To argue with a fool is itself foolish. It requires investing serious time and effort into a battle that can rarely be won and will almost always leave you exhausted, drained and frustrated.

So don’t answer, right?

Except . . . the very next sentence tells us that we should answer, “lest he be wise in his own eyes.” Sometimes silence sounds like agreement and approval. Sometimes there’s an audience involved. Sometimes the foolishness on display requires someone, anyone, stepping in and pointing out the absolute nonsense involved.

So do answer, right?

But what about not becoming foolish ourselves? But what about when something needs to be said—if only because people are giving weight to someone else’s foolish words? But what about entrenching ourselves in an unwinnable argument? But what about making sure someone is advocating for the truth?

But what about, but what about, but what about . . .

Part of the riddle is that when and how to respond to a fool is a very situational decision. It depends on the kind of foolishness and who’s watching. But another part of the riddle is far simpler:

With a truly foolish person, there is no winning. You will lose no matter what you do, and sometimes the choice isn’t about how to win the confrontation, but about how to lose the least amount of your time (and sanity).

For more insight on this proverb, read “Proverbs 26: When Should You Answer a Fool?”

3. The incredible power of laziness (Proverbs 18:9)

A comparison that seems a little odd is in Proverbs 18:9:

“He who is slothful in his work is a brother to him who is a great destroyer.”

Shouldn’t those two be opposites? Destruction requires action, and to be slothful (what some translations call “slack” and what we might call “lazy”) is to be decidedly inactive.

The destroyer chooses action, the lazy man chooses inaction, but both produce the same outcome: Ruin. But the two are called brothers—not because their methods are the same, but because their results are the same.

A destroyer produces destruction. And what does a lazy man produce? Well, initially—nothing. That isn’t the same as destruction—unless work needs to be done.

And there’s always work that needs to be done, isn’t there?

Choosing to do nothing when there’s time-sensitive work on the table—whether that’s a crop that needs to be planted, a field that needs to be harvested, a project that needs to be completed, a message that needs to be conveyed, a repair that needs attention—there will be a consequence. Things will fall apart. Opportunities will vanish. Relationships will crumble.

We don’t have to be violent to destroy.

The destroyer chooses action, the lazy man chooses inaction, but both produce the same outcome:

Ruin.

For more insight on this issue, read “How to Overcome Laziness.”

4. The wealthy poor and the impoverished rich (Proverbs 13:7)

The New International Commentary on the Old Testament calls this proverb “wonderfully ambiguous” because it can be interpreted several different ways:

“There is one who makes himself rich, yet has nothing; and one who makes himself poor, yet has great riches” (Proverbs 13:7).

The two Hebrew verbs translated “makes” can refer to pretending to be or acting a certain way. There are, in other words, rich people who act or pretend as if they’re poor, and there are poor people who act or pretend as if they’re rich.

The contrast is clear, but the exact lesson isn’t. 

It could be a warning that true wealth is about more than possessing physical riches, while true poverty is about more than owning nothing. It could be a criticism of wealthy individuals who pretend to have nothing so they can avoid helping others—and of poor individuals who are so desperate for status that they strive for the appearance of wealth. It could be a simple observation that someone’s financial state is not directly tied to the manner in which they live their lives.

Maybe it’s all three at once. Perhaps it’s something else. But at the very least, this riddle asks us to reflect on the fact that the way things look and the way things are don’t always match up. It also asks us to consider what true wealth really is—and what it looks like to possess it.

For more insight, read “You Cannot Serve God and Money.”

5. A waste of a proverb (Proverbs 26:9)

The whole book of Proverbs was written, in part, “to impart shrewdness to the morally naive, a discerning plan to the young person” (Proverbs 1:4, NET Bible). But just reading and reciting the words of this book isn’t the way to make that happen, as Proverbs 26:9 warns:

“Like a thorn that goes into the hand of a drunkard is a proverb in the mouth of fools.”

Wisdom is wisdom, no matter where it comes from. So why are the wise words like a thorn in this scenario?

Because the ability to speak wise words isn’t the same thing as being wise.

The drunkard has grasped something valuable, but he doesn’t understand it. He’s incapable of understanding it, because he’s spent his time consuming the intoxicants that muddle his mind and hamper his cognition.

Some proverbs are designed to make us too uncomfortable to stay where we are, herding us in the direction God intends us to walk.  Foolish people can recite wise words without ever really understanding them. They can brandish a proverb—grab onto it and wave it around for everyone to see—and never comprehend that the words apply to them.

The book of Ecclesiastes explains, “The words of the wise are like goads, and the words of scholars are like well-driven nails, given by one Shepherd” (Ecclesiastes 12:11).

Goads are pointed sticks used to drive animals in the direction intended by a shepherd or cowherd. Some proverbs are like that—they poke at our conscience. They’re designed to make us too uncomfortable to stay where we are, herding us in the direction God intends us to walk. 

But if we’re drunk—too busy chasing foolish things to notice the prodding—then a wise saying can become a thorn in our hands. We can acknowledge it without feeling its impact in our lives, causing damage to ourselves without even noticing it.

If we only make this proverb a way to look at other people, then we’ve missed the point. Sure, other people can be foolish. Sure, other people can completely miss the connection between the wise things they’re saying and the way they live their own lives.

But what about you?

What about me?

If we aren’t careful, we can become the drunk man grasping the thorns. We must take the time to examine ourselves—to ask God to give us the insight and perspective we need to make sure we’re not somehow overlooking any of the goads He’s using in our life.

Wrangling the riddles

These five proverbs can change your life—if you let them. Each one asks us to look at the world around us a little closer, reevaluating the things we see as important and the way we choose to live:

1. Do we want friends who only tell us what we want to hear, or friends who will tell us the painful truth because they care about us?
2. When should we respond to people who have a track record of ignoring reason and sound logic?
3. If we choose to ignore work that needs our attention, what are we actually choosing?
4. Do we use the way things look as a proof of the way things are? What is true wealth, and how does God expect us to use it?
5. How quick are we to apply proverbs to others and not ourselves? Do we take the time to measure ourselves against God’s standards and see where we’re lacking? How often do we ask for His help to see what we might be missing?

Proverbs is a book of riddles—wise sayings that require our attention and focus to unravel.

The more willing we are to wrestle with the enigmas it offers, the more we stand to benefit.

Photo credit:
Freer Law/iStock via Getty Images

Date Posted: May 5, 2025