Proverbs 5:1 ¶ My son, attend unto my wisdom, and bow thine ear to my understanding:

Proverbs 5:2 That thou mayest regard discretion, and that thy lips may keep knowledge.

Solomon continues to urge his son to pay attention to the wisdom he is trying to impart to him.  He considers it so important to learn discernment and how to make good use of what you know that he repeats it over and over again.

Use of the word “lips” makes a natural transition to the following verses.

Proverbs 5:3 For the lips of a strange woman drop as an honeycomb, and her mouth is smoother than oil:

Proverbs 5:4 But her end is bitter as wormwood, sharp as a twoedged sword.

Proverbs 5:5 Her feet go down to death; her steps take hold on hell.

Proverbs 5:6 Lest thou shouldest ponder the path of life, her ways are moveable, that thou canst not know them.

The father warns his son about the flattering and seductive words used by strange (profane, adulterous) women.  If you fall for her seduction, you will eventually experience her bitterness and anger.  Consorting with her will lead to death and hell.  She is not following the path of life as established by God.  You have no idea where consorting with her will lead you.

Guzik: "Our day is like Solomon’s, or perhaps worse. Modern western culture is saturated with images of alluring women and their enticement to gain something sweet and pleasant from them.”

Proverbs 5:7 Hear me now therefore, O ye children, and depart not from the words of my mouth.

Proverbs 5:8 Remove thy way far from her, and come not nigh the door of her house:

Proverbs 5:9 Lest thou give thine honour unto others, and thy years unto the cruel:

Proverbs 5:10 Lest strangers be filled with thy wealth; and thy labours be in the house of a stranger;

Proverbs 5:11 And thou mourn at the last, when thy flesh and thy body are consumed,

Proverbs 5:12 And say, How have I hated instruction, and my heart despised reproof;

Proverbs 5:13 And have not obeyed the voice of my teachers, nor inclined mine ear to them that instructed me!

Proverbs 5:14 I was almost in all evil in the midst of the congregation and assembly.

The wording again makes me think Solomon is talking to several of his sons and emphasizing personal application when using the word “son.”  He urges his sons to stay far away from this type of woman and not to even get near her house.  If you don’t, you will end up wasting the best years of your life and losing your hard-earned money to her and those connected to her business.  In the end, you will be left grieving over all you have lost as you suffer from the diseases that are a consequence of your sin.  You will despise yourself for not heeding the instruction and correction of those that tried to teach you.  Even worse, your disgrace will be public.

The Apostle Paul counseled young Timothy along the lines of verse 8.

2 Timothy 2:22 “Flee also youthful lusts: but follow righteousness, faith, charity, peace, with them that call on the Lord out of a pure heart.”

Guzik: "One great price of sexual immorality is regret. When we see how empty the promises of sin are and how great the price for those sins is, deep sorrow and regret is a logical response. Many men and women, fallen into the snare of sexual immorality, have wondered: “How did I ever end up here? How could I be so foolish? How could I give up so much for what amounted to so little?”

Proverbs 5:15 ¶ Drink waters out of thine own cistern, and running waters out of thine own well.

Proverbs 5:16 Let thy fountains be dispersed abroad, and rivers of waters in the streets.

Proverbs 5:17 Let them be only thine own, and not strangers’ with thee.

In context, it is obvious that Solomon is painting a word picture of fidelity in marriage.  He has been urging his sons not to consort with adulterous women.  He now urges each of them to enjoy the pleasures of intimacy with his own wife.

Wiersbe: “Solomon compares enjoying married love to drinking pure water from a fresh well, but committing sexual sin is like drinking polluted water from the gutter or sewer…. To commit sexual sin is to pour this beautiful river into the streets and the public squares. What waste!” 

Proverbs 5:18 Let thy fountain be blessed: and rejoice with the wife of thy youth.

Proverbs 5:19 Let her be as the loving hind and pleasant roe; let her breasts satisfy thee at all times; and be thou ravished always with her love.

I liked the CJB for these verses: “Let your fountain, the wife of your youth, be blessed; find joy in her—a lovely deer, a graceful fawn; let her breasts satisfy you at all times, always be infatuated with her love.”

Proverbs 5:20 And why wilt thou, my son, be ravished with a strange woman, and embrace the bosom of a stranger?

Proverbs 5:21 For the ways of man are before the eyes of the LORD, and he pondereth all his goings.

Solomon is basically saying that there is no good reason for choosing to consort with an adulteress.  He reminds his sons that the LORD sees everything we do; nothing is hid from Him.  Not only does He see what we do; He ponders our actions; the Hebrew makes reference to mentally weighing what he sees.  I think that refers to taking into account all the circumstances surrounding the choices we make.

Proverbs 5:22 His own iniquities shall take the wicked himself, and he shall be holden with the cords of his sins.

Proverbs 5:23 He shall die without instruction; and in the greatness of his folly he shall go astray.

Solomon is basically saying that one who rebels against the LORD to follow wicked ways is sure to suffer the consequences of his sin.  Wise instruction is important to life; to reject it leads to death.   

EBC Abridged: “In other words, if the young man is not captivated by his wife but becomes captivated with a stranger in sinful acts, then his own iniquities will captivate him; and he will be led to ruin.”

Clarke: “Most people who follow unlawful pleasures, think they can give them up whenever they please; but sin repeated becomes customary; custom soon engenders habit; and habit in the end assumes the form of necessity; the man becomes bound with his own cords, and so is led captive by the devil at his will.”