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When Naomi and Rus return to Beis Lechem they are living in abject poverty. Rus goes and collects in Boaz's field. When Boaz finds out, instead of inviting these women to live in his home, or providing them with enough funds to sustain themselves he gives Rus a meal and offers to allow her to continue collecting in his field like any other pauper (granted he allows her to take more than her fair share, and offers her protection from harm). Furthermore Naomi is Boaz's sister-in-law, per Bava Basra 91a which lists Elimelech and Boaz as brothers, yet there is no record of him ever having a single conversation with her?

Granted in the end, after much cajoling from Rus, Boaz marries her, but for Boaz, possible the leader of his generation, not to treat his impoverished family with more mercy and hospitality is surprising to me. Do any of the commentaries speak about why Boaz wasn't more directly nice or helpful to Naomi and Rus?

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I think the term "nicer" is a mater of opinion. If you were to view things from a "mitzvah" viewpoint of what was then primarily an agricultural time, Boaz was performing the mitzvah of shich'cha and pe'ah, primarily, by allowing Rut to glean from his field. This is along with sustaining the poor and widowed - another two important mitzvot. Additionally, if you "inject" Rambam's level of charity in the mix, in a sense, Rut was one of his workers (Boaz tells her to glean among the workers), which would be considered the best form of charity. Overall, I think Boaz was being VERY nice. –  DanF May 8 at 19:42

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In actuality, he did treat her exceptionally well, but was very careful not to embarrass either of them. Note Rus 2:19 in which Naomi notices that she had been treated exceptionally well. The commentary to 2:17 states that he instructed his workers to "forget" or "drop" unusual amounts of wheat so that she could glean (legally) a large amount and not realize that he was giving it to her.

Meanwhile Boaz took the opportunity to investigate her character, because he intended to see if it was proper for him to marry her. As a result of his investigations, he decided that she was indeed a proper wife and then acted to make sure that there were no suspicions about his actions and his motives. Note in 3:10 - 3:18. Also the term "six barley" indicates a specific formal gift showing that he intended to marry her but only if it could be done fully legally as a "redeemer". That is why he went to "Ploni Almoni" (Elimelech's brother) to make sure that he was willing to give up his claim.

Taking her into his household would have prevented all of this action.

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