I am an Orthodox Jew and all in my family are Orthodox too. Recently the man I am dating told me that whilst his father is Jewish, his maternal grandmother converted to Judaism through the Liberal Movement, which technically means he is not Jewish according to Orthodox halachah. He attended a Jewish elementary school, works for a Reform Synagogue and considers himself to be Jewish. Indeed, he has a stronger Jewish identity than many people I know who are halachically Jewish! I know that if we were to get married our children would technically be Jewish, through me, but I still have concerns such as: Would we be able to have an Orthodox Jewish wedding? Would my Synagogue call him up/give him a aliyah (honor of being called to the Torah) were he to visit one Shabbat? Would he be counted in a Minyan (quorum for prayer), etc? Are there any other practical implications I haven't thought of that I need to consider? This is a very difficult subject for him as he is quite sensitive about not being recognised as Jewish by other Jews.
You describe yourself as an Orthodox Jew so I want to respond to you as one. Though it may not be the answer you want to hear, you need to hear it directly. I urge you to immediately contact a rabbi with whom you have a personal relationahip to talk this through.
One needs to investigate the conversion by your boyfriend's grandmother, if possible, to determine what actually did or did not take place. If you are right though that it was a non-halakhic conversion, as seems likely from your account, then Jewish law holds that you may not marry him. I am happy to acknowledge his strong Jewish identity and in no way want to impugn his commitment to Jewishness, but this is a matter of Jewish law, in which subjective feelings only go so far. No Orthodox rabbi would marry you without proof that the original conversion was valid unless your boyfriend himself is willing to convert. This far outweights any discussion of his receiving an aliyah or being counted in a minyan, which I want to ignore here in order to focus on the central feature of your question. You are from an Orthodox family and have been raised to respect Jewish law. If your boyfriend wants to make a life with you then I am hopeful that this is something he can appreciate as well.
I recognize that this may be very sensitive for your boyfriend, but there is no way around confronting it directly and honestly. The pain of doing so now is real, but less than the pain of dealing with it down the road after you have a non-Orthodox wedding or have children together. My strong recommendation to you is that you talk this over in person with a rabbi you know and consult with him about how to approach your boyfriend--it may be that you want to speak with your boyfriend and rabbi together. One way of thinking about conversion in a context like this is that it is not about starting over, the way a non-Jew would need to do in order to become Jewish, but about bringing a person's strong subjective reality into sync with the realities of Torah and Jewish law. It can be a completion of a process begun long ago, and his prior Jewish experience and commitment may make this easier in some ways, especially if there is any reason for doubt about the nature of the original conversion.
If you do not deal with this openly and honestly now you will not only have a marriage that is not in accordance with Jewish law and not recognized by halakha but you will also be putting your future children in the position of needing to choose between their own father and the Judaism that you and your family have been committed to. If your boyfriend is not Jewish according to halakha and not interested in becoming so, I can only advise you to respect his decision and move on.
You have an interesting case which gets at the heart of the sensitive question, who is a Jew. What you have outlined is two-fold: The first question is what constitutes a halachik conversion AND the second question is how will your boyfriend be recognized. Allow me to answer them separately.
As a Conservative Rabbi, I believe that a halachik conversion involves a number of steps including associating with a Jewish community, a period of study concluded by a meeting with a bet din where the person articulates their commitment to living a life guided by Jewish values/ethics/traditions, and an immersion in the mikvah with the appropriate brachot. If it is a man converting, then he would also need a circumcision if he never had one, and if he did have one, he would need a “hatafat dam brit” a pin prick of blood drawn from his penis to represent the symbolism of the brit milah. If your boyfriend’s mother had the appropriate steps that I outlined, I would consider her son halachically Jewish. You write however that she was converted thorugh “the Liberal movement.” That is vague as it doesn’t explain the required steps so potentially, if the conversion was being questioned, he might need to find the answers.
As for whether your Orthodox community would see his grandmothers’ conversion as valid-I would certainly hope so if these steps I outlined were done, but in our world today, conversions, even between the Orthodox community can find themselves being questioned. There has been a “tightening of the reins” of sorts, especially in Israel where the Chief Rabbinate are not accepting certain conversions even if they were done under the auspices of Orthodox Rabbis. So, what you and your boyfriend will have to talk about, is what community in which do you see yourselves? If you believe, as it sounds like you do, that he is halachically Jewish, then you need to find a community that represents your understanding of Jewish law, or, conversely, understand that if you enter into a different community, or even the community you are currently a part of, then he might need to take certain steps in order to be a full participating member of that Jewish community.
This is not easy and as you said, very sensitive. I wish you luck and I hope that you find a community and a Rabbi with whom you can enter into these very important conversations without leaving alienated.
I am sure that my Orthodox colleague will fully respond to the specific questions asked and so I only have a few points to add. His recognition as a Jew by other non-Orthodox movements (other than Reform, that is) might depend on the ritual that his grandmother went through. Specifically, did it include a Beit Din (Jewish Court) and immersion in a Mikveh. Also, you should know that your husband would be eligible for Israeli citizenship under the Law of Return but, under the current Orthodox rules, would not be considered a Jew in Israel once he got there.
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