Of meddling with his maidservant: Good News Translation captures this line well with an English idiom; “playing around with” would refer to flirting here and even sexual activity, which is what the author has in mind. Translators should find a word that means “flirting” or even “making sexual advances toward.” The maidservant is not necessarily a slave, as Good News Translation indicates, but may have been. At any rate she is a servant living in the man’s household.

And do not approach her bed: This is a parenthetical expression; notice how it breaks the pattern of what goes before and comes after. Good News Translation handles it well with “keep away from her bed!” Another way to express this is “Don’t even think about sleeping with her!” or “Don’t even try to sleep with her.”

Of abusive words, before friends: Good News Translation provides a good model here with “of insulting your friends.”

And do not upbraid after making a gift: This refers to giving something to someone, and then saying hurtful things to the person. Compare 18.15; 20.14-15. Contemporary English Version has a helpful model for the last two lines:

• if you insult your friends,
even though you have given
a gift to them;

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.