In the twilight, in the evening, in the black and dark night:

In the dark, when it grows late, in the darkness and obscurity of the night,

in the twilight, in the evening of the day, in the blackness of night and the darkness.

In the twilight, in the evening of day, In the darkness of night and blackness.

At nightfall, in the evening of the day, in the black dark of the night.

He steps into shadows, as day becomes evening, into the darkness and gloom of the night.

In the twilight, in the evening - Some time after sun-setting; before it was quite dark.
In the black and dark night - When there were neither lamps nor moon-shine.

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.

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.

The time, twilight, ending in darkness.
black . . . night--literally, "pupil," or, "eye," that is, middle of night.

The 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 = 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.