Proverbs 30:19

ESV the way of an eagle in the sky, the way of a serpent on a rock, the way of a ship on the high seas, and the way of a man with a virgin.
NIV the way of an eagle in the sky, the way of a snake on a rock, the way of a ship on the high seas, and the way of a man with a young woman.
NASB The way of the eagle in the sky, The way of a snake on a rock, The way of a ship in the middle of the sea, And the way of a man with a virgin.
CSB the way of an eagle in the sky, the way of a snake on a rock, the way of a ship at sea, and the way of a man with a young woman.
NLT how an eagle glides through the sky, how a snake slithers on a rock, how a ship navigates the ocean, how a man loves a woman.
KJV The way of an eagle in the air; the way of a serpent upon a rock; the way of a ship in the midst of the sea; and the way of a man with a maid.

What does Proverbs 30:19 mean?

These concepts are the four ideas Agur noted in the prior verse (Proverbs 30:18). Each is a mystery for its own reasons. Commentators differ on whether the four share a common theme. If so, it might be how each example manages a task which seems impossible. Or, in the idea of movement other than along a clear road on the ground. It's also possible that each example is meant to stand alone as evidence of the Creator's amazing handiwork (Psalm 19:1). An especially popular view is that each of the examples is something which—at least at first—leaves no trace. Birds through air, snakes across rocks, and ships through the ocean all happen without leaving obvious, immediate traces. Sex, illicit or legitimate, likewise leaves no easily-seen traces that others might detect.

Agur observed an eagle soaring in the sky and was amazed by it. An eagle flies high and swiftly. It is depicted in Scripture as swooping down (Deuteronomy 28:49), as stirring her nest (Deuteronomy 32:11), as hurrying to her prey (Job 9:26), and as making her nest up high (Jeremiah 49:16). The eagle is mysterious in her flight path and majestic in her appearance. That birds fly, at all, is an amazing effect of their divine design.

Second, Agur is impressed by the motion of a snake across rock. Having no legs or feet, how does a snake travel? Obviously, it twists and curls, but the method is much more complex than it might seem.

A ship on the high seas also earns Agur's admiration. A ship maneuvers in the ocean, although high waves buffet it. Such a massive object can be guided using wind and the influence of a small rudder (James 3:4). Sea travel can be dangerous, especially in the ancient world. But that relatively simple boats could navigate safely, at all, is remarkable.

Modern art often speaks of love and romance as the ultimate mystery. Agur, as well, struggles to understand the interplay between men and women. However, many commentators note that the terminology he uses seems to suggest physical intercourse, more so than courtship. He seems to be referring to something sinful, rather than a man and woman consummating their marriage. He may be comparing the lack of signs which each example leaves. In that sense, two people can come together sexually and no one would know, at first. Beyond pregnancy or simpler evidence, the act in and of itself doesn't result in "tracks" which can be easily followed.

The following verse (Proverbs 30:20) makes note of how those engaged in sexual sin can brush it off as meaningless. If that lesson was meant to connect to this verse, it's more likely Agur was comparing the lack of evidence in his four examples.
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