This translation is from the New Jerusalem Bible. Other translations are available here. Information about the original Hebrew meaning of what seem to be the key words is provided immediately below the scriptural text. A post dealing with part of this chapter is hyperlinked at the end of this post.
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My son, pay attention to my wisdom, listen carefully to what I know; 2so that you may preserve discretion and your lips may guard knowledge.
Take no notice of a loose-living woman, 3for the lips of the adulteress drip with honey, her palate is more unctuous than oil,4but in the end she is bitter as wormwood, sharp as a two-edged sword. 5Her feet go down to death, Sheol the goal of her steps; 6far from following the path of life, her course is uncertain and she does not know it.
7And now, son, listen to me, never deviate from what I say: 8set your course as far from her as possible, go nowhere near the door of her house, 9or she will hand over your honour to others, the years of your life to a man without pity, 10and strangers will batten on your property, and your produce go to the house of a stranger, 11and, at your ending, your body and flesh having been consumed, you will groan 12and exclaim, 'Alas, I hated discipline, my heart spurned all correction; 13I would not attend to the voice of my masters, I would not listen to those who tried to teach me. 14Now I have come to nearly every kind of misery, in the assembly and in the community.'
15Drink the water from your own storage-well, fresh water from your own spring. 16Even if your fountains overflow outside, your streams of water in the public squares: 17let them be for you alone, and not for strangers with you. 18May your fountain-head be blessed! Find joy with the wife you married in your youth, 19fair as a hind, graceful as a fawn: hers the breasts that ever fill you with delight, hers the love that ever holds you captive.
20Why be seduced, my son, by someone else's wife, and fondle the breast of a woman who belongs to another? 21For the eyes of Yahweh observe human ways, and survey all human paths. 22The wicked is snared in his own misdeeds, is caught in the meshes of his own sin. 23For want of discipline, he dies, led astray by his own excessive folly.
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son = בֵּן = bēn Blue Letter Bible son, grandson, child, member of a group; male child; young men; children (pl. - male and female); foster son; disciple; one related to a time, place, emotion, condition, status; term of kindliness or endearment; expression of intimate and gracious relation
pay attention = קָשַׁב = qashab Blue Letter Bible to hear, be attentive, heed, incline (of ears), attend (of ears), hearken, pay attention, listen; give attention; to prick up the ears; regard
wisdom = חָכְמָה = ḥāḵmâ Blue Letter Bible a divine attribute or energy; cleverness; shrewdness; skill; prudence; dexterity; wit; piety towards God
listen carefully = אֹזֶן = 'ōzen Blue Letter Bible ear, as organ of hearing; to uncover the ear to reveal; open ears of, reveal to; to place in anyone’s ear; to hear with anyone’s ears
AND
נָטָה = natah Blue Letter Bible to stretch out, extend, spread out, pitch, turn, pervert, incline, bend, bow; turn aside, incline, decline, bend down; hold out; incline, influence; outstretched; wrest, cause to yield; spread oneself; seduce
understanding = תָּבוּן = tāḇûn Blue Letter Bible understanding, intelligence; the act of understanding; skill; the faculty of understanding; insight; the object of knowledge; teacher (personification); discretion; reason; skillfulness; wisdom
preserve = שָׁמַר = šāmar Blue Letter Bible keep, guard, observe, give heed; retain, treasure up (in memory); preserve; attend to
discretion = מְזִמָּה = mᵊzimmâ Blue Letter Bible purpose, discretion; sagacity; thought; prudence; counsel; power of devising
lips = שָׂפָה = śāp̄â Blue Letter Bible lip, language, speech; edge, shore, bank (of cup, sea, river, etc), border
guard = נָצַר = nāṣar Blue Letter Bible watch over; observe, guard with fidelity; kept close, be blockaded; protect, maintain, obey; preserve
knowledge = דַּעַת = daʿaṯ Blue Letter Bible knowledge, perception, skill; discernment, understanding, wisdom; cunning; knowing; intelligence
loose living woman = זוּר = zûr Blue Letter Bible to be strange, be a stranger; to become estranged; foreigner, an enemy; loathsome; prostitute, harlot; alienated; profane; turn aside; depart; of another family; profligate
drip with honey = חָלָק = ḥālāq Blue Letter Bible flattering, smooth; slippery, deceitful
son = בֵּן = bēn Blue Letter Bible son, grandson, child, member of a group; male child; young men; children (pl. - male and female); foster son; disciple; one related to a time, place, emotion, condition, status; term of kindliness or endearment; expression of intimate and gracious relation
listen = שָׁמַע = šāmaʿ Blue Letter Bible listen to, obey; perceive by ear; hear with attention or interest; give heed; consent, agree; yield to; be obedient; hear intelligently (often with implication of attention, obedience, etc.); hear and answer
deviate = סוּר = sûr Blue Letter Bible turn aside, depart; avoid; be removed; depose; put aside, leave undone, retract, reject, abolish; eschew; turn off; rebel; put away, withdraw; sour; turn aside to oneself; be without
what I say = אֵמֶר = 'ēmer Blue Letter Bible utterance, speech, word, saying, promise; command, mandate; something said; appointed unto him; saying, speech, word
course = דֶּרֶךְ = dereḵ Blue Letter Bible way, road, distance, journey, manner; path; mode; habit, way; course of life; mode of action
far from = רָחַק = rāḥaq Blue Letter Bible be or become far, be or become distant, be removed, go far away; send far away; make or exhibit distance, be gone far; remove, put far away; loose; widen; recede; cast; wander; refrain; a good way off; remote
near = קָרַב = qāraḇ Blue Letter Bible to come near, approach, enter into, draw near; cause to approach
door = פֶּתַח = peṯaḥ Blue Letter Bible opening, doorway, entrance; gate
house = בַּיִת = bayiṯ Blue Letter Bible house, dwelling, habitation, abode; place; receptacle; home; house as containing a family; palace, fortress; inner part, family
hated = שָׂנֵא = śānē' Blue Letter Bible to hate, be hateful; enemy, foe; be odious
discipline = מוּסָר = muwcar Blue Letter Bible discipline, chastening, correction; reproof, warning or instruction; doctrine, instruction, rebuke; admonition; restraint
spurned = נָאַץ = nā'aṣ Blue Letter Bible spurn, contemn, despise, abhor; deride, reject; blaspheme, speak evil
reproof = תּוֹכֵחָה = towkechah Blue Letter Bible rebuke, correction, reproof, punishment, chastisement; argument, impeachment; refutation; chiding; arguing down, contradicting
attend = שָׁמַע = šāmaʿ Blue Letter Bible listen to, obey; perceive by ear; hear with attention or interest; give heed; consent, agree; yield to; be obedient; hear intelligently (often with implication of attention, obedience, etc.); hear and answer
voice = קוֹל = qôl Blue Letter Bible proclaim; command, entreat; claim; sing out; thundering; with a loud voice; voice, sound, noise; call aloud; a voice or sound; bleating, crackling, lowing, neighing, stamping of feet; noise of inanimate objects; lightness, frivolity
masters = יָרָה = yarah Blue Letter Bible point out; show; direct, teach, instruct; throw, shoot, cast, pour; to flow as water (i.e. to rain); point out (as if by aiming the finger); direct, inform, instruct, lay, shew; lay foundations; to sprinkle, water; to send out the hand
listen = נָטָה = natah Blue Letter Bible to stretch out, extend, spread out, pitch, turn, pervert, incline, bend, bow; to turn aside, incline, decline, bend down; hold out; incline, influence; outstretched; wrest, cause to yield; spread oneself; seduce
AND
אֹזֶן = 'ōzen Blue Letter Bible ear, as organ of hearing; to uncover the ear to reveal; open ears of, reveal to; to place in anyone’s ear; to hear with anyone’s ears
teach = לָמַד = lāmaḏ Blue Letter Bible learn, teach, exercise in; to be taught, be trained; to goad; instruct; chastise, discipline; to train, accustom
Drink = שָׁתָה = shathah Blue Letter Bible feast, banquet; be drunk; to imbibe (literally or figuratively); drink up; drink together
water = מַיִם = mayim Blue Letter Bible water; figuratively, juice; by euphemism, urine, semen
storage well = בּוֹר = bôr Blue Letter Bible pit; well, cistern; dungeon; fountain; sepulcher
fresh water = נָזַל = nazal Blue Letter Bible to flow, distil, flow forth or down, trickle, drop; streams, floods (participle); cause to flow; shed by trickling; gush out, melt, pour (down), running water, stream; fluids; like other verbs of flowing; is to be construed as an acc. of whatever flows plentifully
spring = בְּאֵר = bᵊ'ēr Blue Letter Bible well, often made by digging; pit, spring
alone =בַּד = bad Blue Letter Bible by itself; apart; separation; alone, by itself, besides, a part, separation, being alone
stranger = זוּר = zûr Blue Letter Bible be strange, be a stranger; become estranged; foreigner, an enemy; loathsome; prostitute, harlot; alienated; profane; turn aside; depart; of another family; profligate
Find joy with the wife you married in your youth
Find joy = שָׂמַח = śāmaḥ Blue Letter Bible rejoice, be glad; gladden, make glad; brighten up; make blithe or gleesome; cheer up; make merry; take pleasure in; joyful or cheerful
wife = אִשָּׁה = 'iššâ Blue Letter Bible woman, wife, female; together
youth = נָעֻר = nāʿur Blue Letter Bible youth, early life; childhood; adolescence
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Scriptural directions for husbands, annotated—Proverbs 5:15-19
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