Do not associate with a woman singer: The woman in view could be a singer or a player of an instrument (New English Bible “dancing-girl” is less likely). Good News Translation attempts to cover both with “female musicians.” There is evidently something of a cultural nature here that we do not know of, but it seems clear that women who sang or played musical instruments were associated with situations that were morally suspect. In Isa 23.16 prostitutes are spoken of as making music.
Lest you be caught in her intrigues is a little different from “lest you fall into her snares” in verse 3. In verse 3 the Greek word for “snares” describes a physical object, a trap such as might be used to catch animals. Here the word for intrigues describes deliberate schemes, attempts to accomplish something of evil intent. Good News Translation “they will trick you” gets the idea, but comes across as a bit weak. “They will use many tricks to bring you under their control” is not far off the mark.
Quoted with permission from Bullard, Roger A. and Hatton, Howard A. A Handbook on Sirach. (UBS Helps for Translators). New York: UBS, 2008. For this and other handbooks for translators see here.

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