Proverbs 7:9
(9) In the twilight . . .--He has no excuse of sudden temptation to offer; from twilight till dark night he had trifled with danger, and now at last his "calamity comes" (Proverbs 6:15).

Verse 9. - In the twilight, in the evening of the day. So termed to distinguish it from the morning twilight. The moralist sees the youth pacing to and fro in the early evening hours, and still watching and waiting when the darkness was deepest (comp. Job 24:15). In the black and dark night; literally, in the pupil of the eye of night and in darkness. We have the same expression in Proverbs 20:20 (where see note) to denote midnight. Its appropriateness is derived from the fact that the pupil of the eye is the dark centre in the iris. Septuagint: the youth "speaking in the darkness of evening, when there is the stillness of night and gloom."

7:6-27 Here is an affecting example of the danger of youthful lusts. It is a history or a parable of the most instructive kind. Will any one dare to venture on temptations that lead to impurity, after Solomon has set before his eyes in so lively and plain a manner, the danger of even going near them? Then is he as the man who would dance on the edge of a lofty rock, when he has just seen another fall headlong from the same place. The misery of self-ruined sinners began in disregard to God's blessed commands. We ought daily to pray that we may be kept from running into temptation, else we invite the enemies of our souls to spread snares for us. Ever avoid the neighbourhood of vice. Beware of sins which are said to be pleasant sins. They are the more dangerous, because they most easily gain the heart, and close it against repentance. Do nothing till thou hast well considered the end of it. Were a man to live as long as Methuselah, and to spend all his days in the highest delights sin can offer, one hour of the anguish and tribulation that must follow, would far outweigh them.In the twilight, in the evening, in the black and dark night. Which is the usual time adulterers take to commit their works of darkness in, by which they think to conceal them; they being such as they themselves do not care should be seen and known, Job 24:15; their works will not bear the sun and daylight, therefore they take the twilight and when the sun is set; and choose the night, and not light nights neither, but the blackest and darkest nights, as fittest for their purpose; most likely to meet with harlots, and less liable to be seen by their neighbours; but always to be seen by the omniscient God, with whom the darkness and the light are both alike. Perhaps these several words may express the time from the young man's first setting out to his drawing nigh to the harlot's house, and his being attacked and ensnared by her; when he first set out from his own or his father's house, it was "twilight", the sun was declining; by that time he had got good part of his way the sun set, and then it was "evening"; and when he came near the harlot's house it was "black and dark night": and this may represent the gradual and progressive growth of Popery; there was first a "twilight", a decline of the purity of Gospel light and knowledge, and then the sun of the Gospel set, which brought on an "evening", and issued in the gross "darkness" of Popery, represented by the Thyatirian church state, as before observed; since that, the "morning star" of the Reformation has appeared, but this is become obscure, we are in a twilight again; it is neither day nor night with us as yet, but a dark black night is hastening on; and it is easy to observe how many, like this foolish young man, are marching on in a stately manner to the harlot's house, or are verging to Popery, whether they design it or not.
Proverbs 7:8
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