Proverbs 7:9
In the twilight, in the evening, in the black and dark night:
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EXPOSITORY (ENGLISH BIBLE)
(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).

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.Simple - In the bad sense of the word (Proverbs 1:22 note); "open" to all impressions of evil, empty-headed and empty-hearted; lounging near the house of ill-repute, not as yet deliberately purposing to sin, but placing himself in the way of it at a time when the pure in heart would seek their home. There is a certain symbolic meaning in the picture of the gathering gloom Proverbs 7:9. Night is falling over the young man's life as the shadows deepen. 9. The time, twilight, ending in darkness.

black … night—literally, "pupil," or, "eye," that is, middle of night.

In the evening; when the day labour being ended, he was at leisure for any thing; and when such strumpets used to walk abroad for prey.

In the black and dark night; when it begun to be black and dark.

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. In the twilight, in the evening, in the {c} black and dark night:

(c) He shows that there was almost no one so impudent that they were not afraid to be seen, their consciences accusing them and causing them to seek the night to cover their filthiness.

EXEGETICAL (ORIGINAL LANGUAGES)
9. black and dark night] Lit. in the pupil (of the eye) of the night, and the darkness. The Heb. word for pupil is the same as that rendered apple (of thine eye), Proverbs 7:2. It is used again poetically, as here, in Proverbs 20:20, in the blackest darkness, R.V. lit. in the pupil (of the eye) of darkness.

The short twilight of those latitudes is quickly followed by the blackness of night: which things are here perchance an allegory.

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." Proverbs 7:9The designations of time give the impression of progress to a climax; for Hitzig unwarrantably denies that נשׁף means the twilight; the Talmud, Berachoth 3b, correctly distinguishes תרי נשׁפי two twilights, the evening and the morning twilight. But the idea is not limited to this narrow sense, and does not need this, since the root-word נשׁף (vid., at Isaiah 40:24) permits the extension of the idea to the whole of the cool half (evening and night) of the entire day; cf. the parallel of the adulterer who veils himself by the darkness of the night and by a mask on his countenance, Job 24:15 with Jeremiah 13:16. However, the first group of synonyms, בּנשׁף בּערב יום (with the Cod. Frankf. 1294, to be thus punctuated), as against the second, appears to denote an earlier period of the second half of the day; for if one reads, with Hitzig, בּערב יום (after Judges 19:9), the meaning remains the same as with בּערב יום, viz., advesperascente die (Jerome), for ערב equals Arab. gharab, means to go away, and particularly to go under, of the sun, and thus to become evening. He saw the youth in the twilight, as the day had declined (κέκλικεν, Luke 24:29), going backwards and forwards; and when the darkness of night had reached its middle, or its highest point, he was still in his lurking-place. אישׁון לילה, apple of the eye of the night, is, like the Pers. dili scheb, heart of the night, the poetic designation of the middle of the night. Gusset incorrectly: crepusculum in quo sicut in oculi pupilla est nigredo sublustris et quasi mistura lucis ac tenebrarum. אישׁון is, as elsewhere לב, particularly the middle; the application to the night was specially suitable, since the apple of the eye is the black part in the white of the eye (Hitzig). It is to be translated according to the accus., in pupilla noctis et caligine (not caliginis); and this was probably the meaning of the poet, for a ב is obviously to be supplied to ואפלה.
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