Do not look intently at a virgin: The Greek verb translated look intently does not necessarily refer to looking at all, but paying close attention, keeping the mind on, being obsessed with. Virgin will be more naturally translated in many languages as “young woman” or “young unmarried woman.”

Lest you stumble and incur penalties for her: Stumble would mean that you became so obsessed that you had sexual relations with her. So you stumble may be rendered “you have sex [or, lie with / go to be with] her” or “you talk her into having sex” (Contemporary English Version). To do this would incur penalties, that is, you would be required to pay a bride price to the girl’s father. Contemporary English Version expresses this as “you will have to pay a fine and marry her.” Compare Exo 22.16-17; Deut 22.28-29.

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.