Take his garment that is surety for a stranger, and take a pledge of him for a strange woman.
Business optimists and risk-takers are financially dangerous, and so are men who live or play with loose women. Stay away from both types. Do not work for them. Do not invest with them. If you must do business with them, get a very tight contract for protection.
Impulsive and immoral men are going down, and they will take you with them, unless you protect yourself. This proverb has a twin in Proverbs 20:16, which doubles the warning against risk-takers and immoral men. Learn to measure men, and avoid all fools.
Consider the terms. A surety guarantees financial obligations of others, much like a co-signer of loans. A pledge is a performance bond, much like a security deposit, which gives reassurance a person will perform, or it can be retained to cover any damages. A garment in this context is an example of an O.T. pledge – something valuable you hold as a security deposit. A strange woman is any woman who will have sex outside marriage.
King Solomon warned his son against guaranteeing debts of others. With great wealth, connections, and reputation, a prince could easily get himself committed to obligations he might have to end up paying off himself. Since affairs of state involve large obligations with heavy consequences, he taught his son often against this temptation, and you should benefit by these repeated warnings (Pr 6:1-5; 11:15; 17:18; 20:16; 22:26-27; 27:13).
When entering business deals, Solomon taught his son to measure a man’s character and integrity by his risk-taking practices and his relationships with women. If the man was a foolish optimist who guaranteed strangers, then extra security should be taken of him in order to protect any dealings. If the man was a fornicator or adulterer, the same advice applied, because both practices will eventually destroy a man (Pr 22:26-27; 5:8-10; 6:26).
Noble men do not need security deposits taken. You may safely enter any deal with them. They fulfill their duties, meet their obligations, and pay their debts. You can count on them. Their word is as good as a contract – their handshake as good as a security deposit. Much business used to be transacted this way, until governments stopped enforcing contracts and punishing debtors, thieves, and covenant breakers with previous severity.
How can you find and prove such men? They are prudent in all business dealings and avoid risky ventures, so they are seldom hurt by a bad deal (Pr 14:15; 22:3; 27:12). They laugh at Ponzi schemes, mock get-rich-quick programs, and they insure all that they should. Strong men with character keep riches (Pr 11:16; 13:23; 18:9; 21:5,20; 28:19). For this reason there is the opposite proverb, “A fool and his money are easily parted.” If a man has preserved his capital, then you know you have found a strong and wise man.
How else can you find noble men for safe business dealings? Observe their relationships with women. If they are adulterers or party animals, stay far away. If you must deal with them, get a strong contract or guarantee before doing so. If they have little character or conscience in matters pertaining to love, sex, and marriage, then they cannot be trusted in financial matters. Furthermore, libidinous living will eventually destroy them in other ways as well. The adulterer and whoremonger are going down to death and hell.
What is the lesson? Avoid foolish optimism or risk-taking in financial matters yourself. Pessimism is a virtue in business transactions and investments (Pr 14:15; 22:3; 27:12). Examine things very carefully and get other counselors involved to avoid pain (Pr 15:22).
Is there another lesson? Keep your heart and life free from whorish women, for moral and sexual compromise will bring economic trouble. Adultery proves a foolish soul and distorted priorities, and whores are never cheap by any measure (Pr 6:30-33; 23:27).
Is there another lesson? Avoid doing business with, or get extra security from, men who are foolish, hasty, impulsive, naïve, optimistic, or vain talkers in financial matters. Protect yourself by staying away from risk-takers, for their folly will take you down with them.
Is there another lesson? Avoid doing business with, or get extra security from, men who are loose with women, for they show a lack of character, and they are also going down. A man who cheats his wife or another woman’s husband will soon cheat you. Beware!
By the grace and mercy of God, though the elect were strangers to God and as unfaithful as whores to the things of heaven, He sent His only begotten Son to be the Surety of His contract, covenant, promise, and testament of eternal life to them (Heb 7:22; 8:6; 9:15; 12:22-24). And because of His faithfulness and justness, any one of them may confess their sins at any time and be forgiven and cleansed from them all (I John 1:9). You may put all your trust in Him, for He alone is just, perfect, and right in all His ways.