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But was Ruth REALLY Jewish? Did she actually convert? If so, where is that recorded? Was merely saying to Naomi, "where you go, I will go" sufficient for conversion?
This is a complicated conundrum. Because if Rut did indeed convert (prior to her marriage to Naomi’s son, as some sources say) then by what right did Naomi try to convince her to stay in Moav? And if Ruth was not Jewish, then what obligation of Yibum (marriage to a close relative in order to continue the family blood-line) existed?
Some want to say that Ruth "converted" (whatever that may mean) on her way from Moav to Bet Lechem. But there is another possibility to consider: There was a time, when Israel was ascendant & a well-respected nation, when many non-Jews wanted to "jump on the bandwagon" & cast their lot with the Jewish People & convert. They did this not because they wished to come closer to G-d via the Mitzvot, but because Jews & Judaism were popular, the "in thing." So the rabbinic leaders of that time placed a moratorium on conversion.
Nevertheless, there were those who, in spite of this decree, did indeed undergo conversion. And so the rabbis decided, in those cases, to take a "wait & see" approach: If the convert was indeed pursuing a religious lifestyle & clearly following the Torah, then their conversion would be declared retroactively valid. If, however, they maintained a distinctly non-observant daily behavior, then the conversions were ruled to have been falsely bestowed & invalid from the get-go.
This was Ruth & Orpah’s situation: Were they truly, sincerely interested in being Jewish (which included their devotion to Eretz Yisrael), or had they merely gone through the motions in a conversion of convenience? Ruth "passed the test" by her decision to follow Naomi – literally & figuratively - both in her staunch adherence to the Mitzvot & her journey to Israel; Orpah failed, as she simply reverted back to her non-Jewish roots.
The lesson of all this, the clear connection to Shavuot, is dramatic: We made a vow, a commitment at Har Sinai to follow Hashem & the Torah. But did we really mean it, or was it just lip service, pressured by a mountain hanging over our heads? Are we Ruths, who freely chose to follow G-d, with all the hardships & challenges that presented, or are we rebels, born as Jews but not much more?
Shavuot gives us the opportunity to show what we’re truly made of, to re-commit ourselves to a Jewish way of life & re-affirm that Shavua taken so long ago on our behalf.
This Shiur is published also at Rabbi Kaganof's site

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