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Where is there a discussion, if any, that says both Naomi and Ruth were the wives of Boaz? (Because Boaz is the goel / redeemer on Naomi's side of the family, if I understand it correctly.)

The above question stands by itself, but to those who want to know what my other related questions might be, it would be:

Does Halacha allow such a scenario? (I am thinking of course, because polygamy is allowed, but then maybe not, perhaps because of a prohibition that I do not know about.) Does it say or imply anywhere that Boaz was already married and/or had children? (My impression upon reading the story is that Boaz is an old man, which means, in my thinking, he must have been or is married with children, just like any good Jewish guy would.)

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I assume you will not find a source saying Boaz was married to Naami.

As to whether or not Boaz had children previously, there are conflicting accounts in midrashic sources.

The Talmud Bavli in Bava Basra 91a says he made 120 wedding for his sons, but they all died while he was alive. It also states there his first wife died the day Ruth arrived in the land of Israel.

Rashi there points out that he still had sons living at the time he married Ruth in accordance with the rule in Yevamos 62b if one married in his youth, marry again in old age.

Ruth Rabba 6:2 on the other hand says he had no children by the time he was 80. Once the Tzadekes (Naami) prayed on his behalf, he was immediately blessed. Same with the 40 year old Ruth who had no children until the tzadik (Boaz) prayed for her.

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Regarding your second question, as to whether Boaz had prior wives or children:

There is a midrashic tradition, recorded in Bava Batra 91a, that identifies Boaz with the judge Ivtzan, mentioned in Sefer Shoftim 12:8-10.

This Ivtzan is recorded in Sefer Shoftim has having fathered 30 sons and 30 daughters.

However, the tradition recorded in Bava Batra recounts that all 60 of them predeceased him, such that his sole surviving legacy was his son Oved, born of Ruth.

The gemara in Bava Batra 91a also records that Boaz's first wife died on the same day as Ruth came to Israel, so that Boaz was a widower when he married Ruth.

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