Are You a Spy or a Tourist?
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I have a question regarding the Book of Ruth. When Ruth's husband died, she had not yet converted. However, she still spoke about marrying Ploni Almoni. Why? Ruth wasn't even Jewish at the time!
Another question has always baffled me. Have Jews throughout history not encouraged conversion to Judaism? Ruth was a convert – yet it didn't seem that she was discouraged.
The Book of Ruth, which we read in the synagogue of Shavuot morning, indeed requires explanation. The story begins in the land of Moab, with Naomi, her two sons and their wives, Ruth and Orpah. Ruth was a Moabite princess who had converted before marrying Naomi's son. There was a question, however, about the validity of the conversion – for perhaps Ruth only converted because she wanted to marry a Jew.
That's why, when the two sons die, Naomi instructs Ruth and Orpah to stay in Moab: "Go and return each of you to your mother's house." Naomi was fulfilling the directive to discourage potential converts.
The women refused to depart, so again Naomi tried persuasion: "Turn back my daughters. Why should you come with me?"
This prodding was strong enough to send Orpah packing. Ruth, however, was persistent, and responded with one of the most famous speeches in the Bible: "Wherever you go, I will go; wherever you lodge, I will lodge. Your people shall be my people, and your God my God. Where you die, I will die, and there I will be buried."
With these words, Ruth indicated that she had left paganism, and clung to Judaism out of her own free will. Thus everyone knew that original conversion had been sincere – and not just for the sake of marriage.
(sources: Ruth 1:8-17, Midrash Ruth, and Zohar Chadash – Ruth 78a)
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Did Naomi explain to Ruth what would be required for her to convert to Judaism?
Yes, the Talmud infers from their recorded conversation that Naomi communicated with Ruth a sample of the laws she would have to observe. Their conversation alludes to other aspects of conversion as well. See here for a longer discussion of this.