Spendeth - The laws of parallelism would lead us to expect "troubleth his father," but that is passed over as a thing about which the profligate would not care, and he is reminded of what comes home to him, that he is on the road to ruin.
The king - The ruler, as the supreme fountain of all justice, and as the ideal judge, is contrasted with the taker of bribers.

But he that keepeth company - רעה roeh, he that feedeth harlots, יאבד yeabed, shall utterly destroy his substance. Has there ever been a single case to the contrary?

Whoso loveth wisdom rejoiceth his father,.... He that is a philosopher, especially a religious one, that not only loves and seeks after natural wisdom, but moral wisdom and knowledge; and more particularly evangelical wisdom, Christ the Wisdom of God, who is to be valued and loved above all things; the Gospel of Christ, which is the wisdom of God in a mystery; and the knowledge of it which is the wisdom which comes from above and is pure and peaceable; and which lies much in the fear of God, and in the faith of Jesus Christ, attended with all the fruits of righteousness: such a son makes glad his father, both because of his temporal good, since he does not waste but improve the substance he has given him; and because of his spiritual and eternal welfare; and since instead of being a reproach he is an honour to him; see Proverbs 10:1;
but he that keepeth company with harlots spendeth his substance: his father has given him, and comes to want and beggary; all which is a grief to his parents: or, "that feeds harlots" (i); who live in a riotous and voluptuous manner, and soon drain a man of his substance, and bring him to a morsel of bread; see Luke 15:13; and such a son grieves his father, seeing he spends his substance and damns his soul.
(i) "nutrit", V. L. "pascit", Pagninus, Piscator, Gejerus, Schultens; "pascitur", Michaelis; "pascens", Montanus, Mercerus.

Divine wisdom best keeps us from ruinous lusts.

(Compare Proverbs 4:6-7; Proverbs 10:1, &c.).

This political proverb is now followed by one of general ethics:
3 A man who loveth wisdom delighteth his father;
And he who keepeth company with harlots spendeth his substance.
Line first is a variation of Proverbs 10:1. אישׁ־אהב has, according to rule, the Metheg, cf. 9a. אישׁ is man, without distinction of age, from childhood (Genesis 4:1) up to ripe old age (Isaiah 66:13); love and dutiful relation towards father and mother never cease. Line second reminds of Proverbs 28:7 (cf. Proverbs 13:20).