Sayings 19-25: Wisdom and strength.
v.1-2 (Saying 19) Evil men. Do not desire to be like evil men nor to be with them (23:17, Ps 37:1-2). They devise trouble within their hearts (Ps 5:9) and will entangle you in it. See 1:10-19. Perhaps one of the greatest threats to a young man’s morals is pressure from his peer group. Teach them that the righteous shall live by his faith (Hb 2:4b).
v.3-4 (Saying 20) Build a house. A house is built (and its rooms filled with precious wealth) by wisdom, understanding and knowledge. This is more than just and physical house, it also addresses family relationships. The needed wisdom, understanding and knowledge flow from the fear of the Lord (1:1-7). Recall also that God created the cosmos by his wisdom (3:19-20).
v.5-6 (Saying 21) The wise man is strong. Wisdom is the key to success in all areas of life. Victory in any endeavor requiring strength is ensured by wise guidance and an abundance of counselors. The wise are mightier than the strong (nlt).
v.7 (Saying 22) Wisdom. Wisdom is an unattainable treasure for a fool (14:6). He is at a loss for words when a word of wisdom is needed. Rulers need wisdom to rule (1 Kgs 3).
v.8-9 (Saying 23) Evil reputation. Those whose lives are characterized by evil plans get a reputation for it and are despised by mankind. The scheming of fools (any scheme the fool thinks up, gnt) is sin and they will be alienated from the community.
v.10 (Saying 24) Strength. Here we are exhorted to be strong in the face of adversity (Gal 6:9). See Heb 12:3. By implication, a wise man has strength under pressure, e.g. see Dn 3:16-18.
v.11-12 (Saying 25) Integrity of character. We must act with strength of character in the face of adversity, especially when the week and needy are in need of deliverance (Ps 82:4). A person’s actions reveal the true state of his heart (and God certainly knows it) and we will be repaid according to our work.

Read Proverbs 24:1-12

Get the truth, wisdom, discipline, and good judgment.
v.22-25 (Saying 16) Obtain truth. Listen to your parents and do not despise them when they are old. The parents of the righteous will rejoice; so let your father and mother be glad. Expend your energy on obtaining truth, wisdom, instruction (discipline), and understanding (good judgment) (see 4:5).
v.26-28 (Saying 17) Model virtue. The parent must model the virtue they want to impart in their children (observe my ways). A prostitute (and adulteress) is a dangerous trap and a robber. Avoiding sexual sin is another of the main themes of Proverbs (7:25-27).
v.29-35 (Saying 18) The folly of drunkenness. The one who drinks to excess will have woe, sorrow, strife, complaining, wounds without cause, and redness of eyes. Wine goes down smoothly, but in the end bits like a serpent. The drunk will see strange things, utter perverse things, and stumble around like on a vessel at sea. The saying ends with a little humor describing a drunk being beaten up but not feeling it and when he wakes up asking for another drink. Those led astray by drinking cannot be wise (20:1).

Sounds like a good prescription for young (or old) people: (1) Listen to your parents, (2) keep far from sexual sin, and (3) don’t drink alcohol to excess.

Read Proverbs 23:22-35

Sayings 13-15: Fear the Lord and avoid slumber and drunkards.
v.15-16 (Saying 13) Follow wisdom. Children bring joy to parents when their heart follows wisdom and when they speak what is right and true. The child with a wise heart will make wise choices. See 10:1.
v.17-18 (Saying 14) Fear the Lord. Walk in the fear of the Lord and make pleasing him your priority. If you walk on that path there is hope in your (eternal) future. Don’t envy sinners (Ps 37:1) and your hope will not be cut off. The fear of the Lord is the main theme of Proverbs (1:7).
v.19-21 (Saying 15) Do not slumber. Here the parent directs the child to be wise and walk in the way (of wisdom). Overindulgence in food (23:1-3), wine (23:19-35), or sleep (10:5) results in poverty.

Proverbs 23:15-21

Sayings 9-12: Applying your heart to wisdom.
v.9 (Saying 9) Advice to a fool. Don’t give advice to a fool, he will just despise you for your good sense. Wisdom in a fool’s ear is wasted breath. See 9:7-8 (don’t bother correcting a mocker).
v.10-11 (Saying 10) Strong redeemer. Do not move the ancient landmark of your neighbor (22:28) or enter take the fields of the defenseless orphan. The Lord himself is their strong redeemer (Ps 119:154) and will plead their cause against you. The wise man will avoid any unfair business practice whether done surreptitiously or in the courts.
v.12 (Saying 11) Knowledge. Apply your heart to instruction and listen (very carefully) to words of knowledge. See 2:2-3. Wisdom cannot be obtained without dogged determination. Echos 22:17.
v.13-14 (Saying 12) Discipline. Warning to not withhold discipline (or instruction) from a child. If you spank him he will not die, but rather you will save his soul from Sheol. Discipline has character building as its goal, not merely behavioral change. You spank not out of anger, but out of a desire to teach your child good virtues. Discipline is rooted in love, 13:24.

Read Proverbs 23:9-14

Sayings 6-8: Deceptive delicacies.
v.1-3 (Saying 6) Deceptive food. Do not desire the delicacies of the rich man for they are deceptive. When dining with a ruler don’t have a big appetite, carefully consider what is put before you (Ps 141:4).
v.4-5 (Saying 7) Don’t try to get rich. Don’t spend your energy trying to get rich, be wise enough to desist, for when you see it it sprouts wings and is gone. There are things in life more important than riches (8:18-21).
v.6-8 (Saying 8.) The stingy man. Don’t eat with a stingy man (28:22). They are always worrying about how much it costs. “Eat and drink,” they say, but they don’t mean it. You will vomit up what you have eaten.

Read Proverbs 23:1-8

The first five of thirty sayings.
v.22-23 (Saying 1.) Don’t rob the poor. Do not rob the poor because he is poor and do not oppress the afflicted (Zec 7:10) because the Lord himself will plead their cause and rob the life from him who robs them. Be generous to the poor, 28:27.
v.24-25 (Saying 2.) Avoid the angry. Do not make friends with an angry or wrathful man (we are speaking of one characterized by anger/wrath) or you will learn his ways (or pick up his habits) and be caught in a snare yourself (or endanger your soul). The wise man will choose his friends very carefully. See 13:20 (we are influenced by those we associate with) and 1 Cor 15:33 (bad company corrupts good character).
v.26-27 (Saying 3.) Don’t put up security. Do not guarantee (pledge/put up security) another man’s debt. If you can’t pay you may lose the coat off your back or the bed from under you (financial ruin). See 6:1-5 (don’t put up security).
v.28 (Saying 4.) Landmarks. Do not move the ancient landmark that was set by your fathers (and thereby defraud your neighbor). See Dt 19:14 where the law prohibits this practice.
v.29 (Saying 5.) Skillful work. The man skillful in his work will stand before kings (and not some obscure men). Work hard and learn to work skillfully and you will work for the best people.

Read Proverbs 22:22-29

The Thirty Sayings of The Wise (Prv 22:17 – 24:22).

Prologue (v.17-21)
v.17-18 Pay attention. The student is instructed to hear the instructions of the wise and apply them to his heart. The result will be pleasant if he keeps them within himself and ready on his lips.
v.19 Trust in the Lord. One purpose of the sayings is that the student (even you) trust in the Lord God.
v.20-21 Counsel and knowledge. Another purpose of the 30 sayings (filled with advice and knowledge) is so that the student (or you) will know what is right and true and be able to give an answer to those who sent him (i.e., those who seek advice).

Read Proverbs 22:17-21

The eyes of the Lord keep watch.
v.8 Injustice. If you sow injustice (or, iniquity), you will harvest disaster and your ability to oppress others will come to an end. The wicked reap what they sow. See Jb 4:8 and especially Gal 6:7-8. (In the LXX there is an additional proverb after this verse: “God loves a cheerful giver….” quoted in 2 Cor 9:7.)
v.9 Bountiful giving. Whoever gives bountifully to the poor (i.e., food) will be blessed (enriched). See 19:17 (the Lord will repay) and 2 Cor 9:6 (reap bountifully). Compare Dt 15:7-11. Give to the poor generously.
v.10 The scoffer. The scoffer, who cannot be changed with discipline or instruction, must be driven out to end strife, quarreling and abuse.
v.11 The pure in heart. In contrast to the scoffer of the last verse, the pure in heart and gracious in speech will have the king as a friend (even a bad king wants someone with these traits as his counselor). Cf. Mt 5:8. It starts with a pure heart because words are a reflection of what is in the heart (16:23).
v.12 The eyes of the Lord. The Lord keeps watch over (protects) knowledge (teachings of wisdom) and so he overthrows the words of the faithless (so that truth alone endures). See 15:3.
v.13 The sluggard. “There is a lion outside, I’ll be killed, so I think I’ll take a nap.” Lazy people will come up with any excuse for not working. (The reality of poverty is what will devour him not his imaginary lion.) See 26:13.
v.14 Forbidden woman. The mouth of the forbidden woman (her seductive words) is a deep pit (or dangerous trap) and he whom the Lord is angry with will fall into it. See also Eccl 7:26.
v.15 Discipline. A child’s heart is bound up with folly, but the rod of discipline drives it from him. It takes discipline to turn foolishness into wisdom. See 13:24 (love disciplines).
v.16 Oppression of the poor. If you oppress the poor to increase your own wealth, or shower the rich with gifts (bribes?), you will come to poverty in the end. The only way to get ahead is hard work.

This ends the second collection of Solomon’s proverbs (15:30-22:16).

Read Proverbs 22:8-16

Humility and fear of the Lord.
v.1 A good name. Always choose a good reputation over great riches (Eccl 7:1a). A good name is much more valuable than a gold egg in a silver bowl. There is certainly nothing wrong with riches, but if you have to choose between the two, choose a good name. Wealth can quickly disappear, but a good name will last.
v.2 God’s creation. The rich and the poor have something in common: the Lord of creation made both of them. Remember this and have mercy on the poor you come into contact with (14:31).
v.3 Prudence. The prudent man sees danger coming and avoids it (takes precautions) while the simple continues (blindly) on and suffers harm as a result (he walks right into it). Parallel in 27:12 and 14:16.
v.4 Reward. The humble and those who fear the Lord will have as a reward riches, honor and (long) life (or satisfying life, MSG). See 3:16 where Wisdom is said to offer riches and honor and a long life.
v.5 Thorns and snares. Watch out for the thorns and snares (dangers in life) that are in the way of the crooked (corrupt). If you guard (value) your soul (life) you will steer clear of them. See 15:19.
v.6 Train a child. Parents who train their children in the way (of wisdom) they should go will find that when they grow up they will stay on that path. See Eph 6:4.
v.7 The borrower. The borrower is the slave of the lender and the rich rule over the poor. This proverb is a warning to not be a borrower (or to guarantee someones debt). See Jas 2:6.

Read Proverbs 22:1-7

Sins of pride.
v.24 Pride: the scoffer. An arrogant, prideful, haughty man is called a “scoffer” (or mocker). Blessed is the man who stays away from scoffers (Ps 1:1). Scoffers refuse to learn from wisdom (13:1) and will be punished, 19:29.
v.25-26 The sluggard. The sluggard (lazy) refuses to do his labor and is overcome by his desires (13:4). He craves, craves, and craves all day long, while the righteous gives without holding back (the more you give the more you get, 11:24). His unfulfilled craving kills the sluggard.
v.27 Wicked sacrifice. The sacrifice of the wicked is unacceptable especially when he brings it with evil intent (also 15:8). If your heart is not right with God you gain nothing from a sacrifice. For Christians I understand this as hypocritical worship (vice wicked sacrifices). You must truly repent and worship God in spirit and truth (Jn 4:24).
v.28 False witness. A false witness will not stand (19:5); but the word of he who listens (to wisdom) will endure. This suggests that the false witness does not listen well.
v.29 Bold face. The wicked bluff their way through a situation, but the righteous think carefully before they speak and act.

Sovereignty of God.
v.30 Prevail. No wisdom, understanding or counsel (plan) can prevail against the Lord. See v.1.
v.31 Battle. The horse (main battle tank) is made ready for battle, but the victory belongs to the Lord. Military power is impotent without the Lord’s blessing.

Read Proverbs 21:24-31