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Sirach 42 alludes to Deuteronomy 24 with similar language about a husband's displeasure and the act of divorce, and the use of “to hate” that introduces separation in both. This connection is notable because later traditions rarely mention divorce.
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2500 BCE
1000+ CE

Deuteronomy 24:1

Hebrew Bible
1 If a man marries a woman and she does not please him because he has found something indecent in her, then he may draw up a divorce document, give it to her, and evict her from his house. 2 When she has left him she may go and become someone else’s wife. 3 If the second husband rejects her and then divorces her, gives her the papers, and evicts her from his house, or if the second husband who married her dies, 4 her first husband who divorced her is not permitted to remarry her after she has become ritually impure, for that is offensive to the Lord. You must not bring guilt on the land that the Lord your God is giving you as an inheritance. 5 When a man is newly married, he need not go into the army nor be obligated in any way; he must be free to stay at home for a full year and bring joy to the wife he has married.
Date: 750–400 BCE (based on scholarly estimates)

Sirach 42:9

Ben Sira, Ecclesiasticus
Deuterocanon
8 Don’t be ashamed to instruct the unwise and foolish, and one of extreme old age who contends with those who are young. So you will be well instructed indeed and approved in the sight of every living man. 9 A daughter is a secret cause of wakefulness to a father. Care for her takes away sleep— in her youth, lest she pass the flower of her age; when she is married, lest she should be hated; 10 in her virginity, lest she should be defiled and be with child in her father’s house; when she has a husband, lest she should transgress; and when she is married, lest she should be barren. 11 Keep a strict watch over a headstrong daughter, lest she make you a laughingstock to your enemies, a byword in the city and notorious among the people, and shame you in public.
Date: 195–180 BCE (based on scholarly estimates)
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Notes and References

#2461
"... References to divorce in the intertestamental literature are sparse. Marcus apparently saw no need to include the subject in his discussion of halakhah in the Apocrypha or to include the Pseudepigrapha under his purview. Only three passages in Ben Sira possibly relate to the termination of marriage. These are Ben Sira 23:22–27; 25:2; and 42:9. Closer scrutiny indicates that 23:22–27 does not really refer to divorce. Ben Sira 42:9 utilizes the same term, “to hate,” that occurs at Elephantine and at Deuteronomy 24:3 and that is taken as introductory to divorce. Ben Sira 25:2 appears to allow divorce for any reason, Hillelite style ..."
Phillip Sigal, The Halakhah of Jesus of Nazareth according to the Gospel of Matthew, StBibLit 18 (Atlanta: SBL, 2007), 130.

* The use of references are not endorsements of their contents. Please read the entirety of the provided reference(s) to understand the author's full intentions regarding the use of these texts.

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