Proverbs - Chapter 27
Friendship
Don't brag about something that hasn't happened yet, because who knows what tomorrow will bring? It's far better to accomplish something and let others praise you than to toot your own horn over plans that may never see fruition. (Even after the fact, it's better to be praised by a third party than to do it yourself.) The anger of a fool is a heavier burden than stones and sand. (This could refer either to the fool's own anger or to that which He arouses in G-d.) Wrath leads to cruelty and anger leads to destruction, but who can stand up before G-d when they incite His "jealousy?" (Remember, our relationship with G-d is like a marriage and He is "jealous" when we "cheat" on Him with false "gods.")
It's better to openly chastise someone than to withhold the criticism because you like the person. "Wounds" caused by a loved one are better than "kisses" from an enemy. A person who is complacent will spurn good things, but a person who is "hungry" will take all he can get. (This is phrased in terms of hunger, but can be seen as a metaphor for Torah study.) A student who wanders from his studies is like a bird wandering from its nest. A friend's advice should be as pleasant to a person as oil and incense; one should consider it more valuable than one's own ideas.
Don't neglect G-d, Who has been a friend to us and to our fathers. Don't rely on the other nations, even though they are related to us, because they have historically let us down. G-d is closer in times of trouble than any person could ever be.
Solomon says that he will rejoice if the reader becomes wise; he will bask like a father in the success of a son. Clever people see sin and avoid it (and the punishment it brings), while fools walk right into it and pay for it. If someone co-signs a loan and the borrower defaults, he will have to pay; he got himself into this mess.
A person who loudly praises his friend every day is actually doing him a disservice; he draws attention to his friend and creates more burdens for him. (Rashi also cites a Midrash applying the verse to Balaam, who praised the Jews as part of an effort to curse them.) An argumentative woman drives her husband out of the house, just like a constant drip from a leaky roof. Trying to rein in such a person is like trying to steer the wind; she brings trouble upon him. (Verse 16 refers to oil of one's right hand, which Rashi says refers to the oil placed on the right hand of a leper, as seen in Leviticus 14:17.)
As iron is used to sharpen iron, so does one scholar sharpen another, intellectually. The one who guards his tree will enjoy its fruits. (Again, the tree is a metaphor for Torah, the "tree of life," as in 3:18.) Just as water shows you the reflection of your own face, so does a person's actions towards another reveal the way he feels about him. Just as the grave will never be satisfied that it has claimed enough lives, so too a person's lusts can never be satisfied; if you think you can feed your desires and they'll cease to hunger, you're mistaken.
Just like gold is refined in a fire, a person's character is tested by the praise he receives. Even if one would crush a fool, like a pestle grinding in a mortar, he would not abandon his foolishness. Pay careful attention to your personal and business affairs, so you'll understand what their needs are. Appreciate the little things because your money won't last forever. When hay is gathered, grass remains. This grass feeds the flocks, who can provide wool and milk to support your family. (In addition to its literal meaning, Rashi explains this section as metaphorically referring to Torah scholars. Understand the character of the teacher appointed to lead the community, whose teachings will be disseminated and who will raise students in his example.)