==Proverbs 5:1-6:

My son, pay attention to my wisdom; Lend your ear to my understanding,
2 That you may preserve discretion, And your lips may keep knowledge.
3 For the lips of an immoral woman drip honey,
And her mouth is smoother than oil;
4 But in the end she is bitter as wormwood, Sharp as a two-edged sword.
5 Her feet go down to death,
Her steps lay hold of hell.
6 Lest you ponder her path of life— Her ways are unstable;
You do not know them.

Stuart Chase Files

"Solomon begins by exhorting his son to listen to him, for this is a matter of the utmost importance. If he heeded Solomon’s warning, he would both “keep discretion” (i.e. live a life in keeping with God’s ethics) and “guard knowledge” with his lips (i.e. speak in a way that honours God’s truth).
The “forbidden woman,” on the other hand—that is, any woman who is not your wife—speaks with lips that “drip honey” and “her speech is smoother than oil.” She is not interested in truth; what she promises appeals only to the senses. She promises physical pleasure. She knows what to say in any given moment. She knows how to seduce. But the son who has “wisdom” and “understanding” (v. 1) will realise that “in the end she is bitter as wormwood, sharp as a two-edged sword” (v. 4). All she can deliver is bitterness and stabbing conviction.
Ultimately, she leads astray and takes those she seduces to death. “Sheol” is a reference to the grave and is synonymous in this context with “death” (v. 5). The sexual expression that she offers satisfies in the moment, but ultimately it leads to death.
Verse 6 is perhaps better translated in the NKJV: “Lest you ponder her path of life—her ways are unstable; you do not know them.” The KJV may be even closer to the point: “Lest you ponder the path of life, her ways are moveable, so that you cannot know them.” (I have slightly updated the archaic language of the KJV to make the point, I trust, a little clearer.) She cannot afford to allow her client to think about God—because when we think about God, we steer clear of sin—so she adapts in order to keep him distracted. --Stuart Chase; Associate Pastor; Brackenhurst Baptist Church; Alberton South Africa; Let’s Talk about Sex (Proverbs 5:1–23); 5.20.18

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Steve Gallagher Files

"Solomon said, "For the lips of an adulteress drip honey and smoother than any oil is her speech." (Prov 5:3). This phrase describes how the devil presents temptation. Honey represents promised  fulfillment. The temptation seems irresistible because it is laced with deception that the act of sin will bring about tremendous pleasure and satisfaction. The tantalizing thought is presented, all is forgotten and the act of sexual sin looks absolutely intoxicating and therefore irresistible."
                             --Steve Gallagher; At The Idol of Sexual  Idolatry

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==Proverbs 5:1-7-8:

Therefore hear me now, my children,
And do not depart from the words of my mouth.
8 Remove your way far from her,
And do not go near the door of her house,

​This chapter tells of wisdom about marriage by first uncovering the surface appeal of the seductive woman (vv.1-6), then warns of the cost of the hidden destruction (vv.7-14), and finally enlarges on the lasting pleasure of a faithful marriage (vv.15-23). A seductive immoral women may sound as sweet as honey and as smooth as olive oil but she has missed the path that leads to life and doesn’t even know it, and if you follow her she will lead you to the world of the dead. The Fathers advise is to, “Keep your way far from her” (v.8). --Daily Reading

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==Proverbs 5:9-14:

Lest you give your honor to others,
And your years to the cruel one;
10 Lest aliens be filled with your wealth,
And your labors go to the house of a foreigner;
11 And you mourn at last,
When your flesh and your body are consumed,
12 And say:
“How I have hated instruction,
And my heart despised correction!
13 I have not obeyed the voice of my teachers,
Nor inclined my ear to those who instructed me!
14 I was on the verge of total ruin,
In the midst of the assembly and congregation.”

==Proverbs 5:5-18:

Drink water from your own cistern,
And running water from your own well.
16 Should your fountains be dispersed abroad, Streams of water in the streets?
17 Let them be only your own,
And not for strangers with you.
18 Let your fountain be blessed,
And rejoice with the wife of your youth.

​Would you drink muddy water? Or, if you lived long before water was piped to homes but had a lovely well on your property, would you want the water to be wasted and sloshed on the village streets? The obvious answer for both questions would be 'definitely not!'. In a similar way the father here was urging his son to treat marriage with the same care. He uses the picture of ‘wells’ and ‘streams’ in vs 15-17 to illustrate his point. It was a discreet way of talking about the marriage bed. The New Testament book of Hebrews says: “Let marriage be held in honour among all - and let the marriage bed be undefiled - because God will judge the sexually immoral and adulterous.” Hebrews 13:4. -Bethel Church Ripon

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==Proverbs 5:19:

As a loving deer and a graceful doe,
Let her breasts satisfy you at all times; And always be enraptured with her love.

Jon Gleason Files

"Proverbs 5:19 is God-inspired Scripture, yet those who speak reverently of God’s gift of marriage and are careful about purity rarely teach it.  This is understandable, for both the Hebrew and English wording are very direct on the pleasures of marriage.  Yet, it creates a problem, for into the gap have stepped the kind of preachers who think it is a good idea to preach God’s Word while wearing a Mickey Mouse shirt, preachers who may often misuse this passage.
The verse, understood properly, refutes the pleasure-worship which pervades society and mars many Christian marriages.  Many modern translations neglect a wordplay in the original Hebrew.  In this post, we’ll look at just enough Hebrew to help English readers understand why the Authorized Version translators handled this verse as they did, but mainly we’ll look at what this verse says to believers living in a pleasure-crazed world."     -Jon Gleason; Mind Renewers; 6.17.13

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​August 12, 2025: Crossway reported: 
​Contrary to Gnostic, body-shaming tendencies within some strands of Christianity, the human body and its sexual functions are neither dirty nor demeaning in God’s created order. As Keller says, “Biblical Christianity may be the most body-positive religion in the world.”4 God created male and female bodily differences and celebrates their goodness. He created sex as a gift and encourages it (see Prov. 5:19; 1 Cor. 7:3–5; and especially Song of Solomon). Structured as a chiasm with an orgasm at the center (“come to his garden,” Song 4:16; “I came to my garden,” Song 5:1), Song of Solomon is one big, beautiful celebration of heterosexual sex as a pleasurable gift. Uncomfortable truth indeed!

==Proverbs 5:20:

For why should you, my son, be enraptured by an immoral woman,
And be embraced in the arms of a seductress?

==Proverbs 5:21:

For the ways of man are before the eyes of the Lord, And He ponders all his paths.

There is no place you can go, no path you can take, where God cannot see. This ought to serve as both a warning and an encouragement. Throughout my day, God sees me. Even more convicting, God is with me.
Yet if this were the only knowledge of God I had, I suppose it would mean little. If I didn’t know His holiness, the fact that He sees my sin would not terrify me. If I didn’t know His love, the fact that He sees my trouble would be of no comfort. But in all things He is perfect, He is present, He is near, He is approachable.

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==Proverbs 5:22-23:

His own iniquities entrap the wicked man,
And he is caught in the cords of his sin.
23 He shall die for lack of instruction,
And in the greatness of his folly he shall go astray.​

Steve Gallagher Files

"Jesus said, "Truly, truly, I say to you, everyone who commits sins is the slave of sin." (John 8:34). Paul said, "Do you not know that when you present yourselves to someone as slaves for obedience, you are slaves of the one whom you obey, either of sin resulting in death, or of obedience resulting in righteousness.?" (Romans 6:16). Solomon wrote, "His own iniquities will capture the wicked, and he will be held with the cords of his sin." (Prov 5:22). And the Psalmist said, "There were those who dwelt in darkness and in the shadow of death, prisoners in misery and chains, because they had rebelled against the words of God, and spurned the counsel of the Most High (Psalms 107:10-11). --Steve Gallagher; At The Idol of Sexual  Idolatry

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