Is it not appropriate to ask a rabbi if he is a Baal Teshuvah, why or why not?
Shalom, Thank you for your question. The issue of what questions are appropriate to ask, and what is not, is a good one. But first let me say that in general there is no difference whether the person is a rabbi or not. We are obligated to honor all mankind – and treat all people with respect. It is true that we have an additional command to further honor Torah scholars, and as such we generally treat our rabbis with even greater respect than other people – but in this case there is no difference, and the types of questions that are not appropriate for a rabbi will generally be inappropriate to ask most people. The issue you raise comes from a command not to let our speech cause pain to others. There is a verse in Lev. 25,17 which the Talmud explained is referring to verbal mistreatment. The Talmud (Babab Matzia, 58b) states “The Sages taught: It is written: “And you shall not mistreat [tonu] one man his colleague; and you shall fear your G-d, for I am the Lord your G-d” (Leviticus 25:17). The tanna [=sage] explains: The verse is speaking with regard to verbal mistreatment.” From this understanding of the verse, the law rules that any speech that is unnecessarily painful to another person is forbidden. This goes beyond the laws of Lashon HaRah (gossip) which forbids one from speaking badly about someone to a third person. Here it is forbidden to say something even in private to another person if what one says will cause them pain. For example it is forbidden to say to someone “you look fat!” or “you're so lazy”. Even if no one else is present, such talk causes pain and is forbidden. (There are cases where such talk is needed for positive reasons – such as a dietitian who needs to wake a client up to the facts, or a teacher who needs to educate a student into working harder – but statements like these made without such a reason are forbidden). One of the examples the Mishna (ibid) brings is as follows “One may not say to a seller: For how much are you selling this item, if he does not wish to purchase it. He thereby upsets the seller when the deal fails to materialize.” From here we see talk which is aimed merely at causing pain to the shopkeeper is forbidden. (However is one is truly interested in the price, and is not asking just to hurt the seller it is permitted to ask the price). The next example in the Mishna is your case - “If one is a penitent, another may not say to him: Remember your earlier deeds. If one is the child of converts, another may not say to him: Remember the deeds of your ancestors, as it is stated: “And a convert shall you neither mistreat, nor shall you oppress him” (Exodus 22:20).” If one is a ba'al tshuva one may not harm them with words that remind them of their former sinful state. So saying things to a ba'al tshuva like “so what does a Big Mac taste like? You must know, you've eaten them” is talk that causes pain to the person, and is forbidden. Recalling a person's faults and weaknesses, even if they are now past history, in general causes pain and must be avoided. The question is, does just asking “are you a ba'al tshuva” itself cause pain? That would very much depend on the situation. In many cases asking someone if they grew up in a religious home does not cause them any pain, as it is rather a good thing to have merited to have come from a non-religous background and then become religious. The mishna is talking about a ba'al tshuvah who is a person who was religious and then sinned, only afterwards returning to the correct behavior. By reminding them of their earlier behavior one is recalling their guilt. This is not the case of today's ba'al tshuvah, who have no blame for their non-religious past, which was just a result of their upbringing. As such recalling that someone is a ba'al tshuva itself is not necessarily rude or painful. On the other hand, in many cases this can cause pain. For a rabbi, for example, recalling that he comes from a non-religious upbringing might cause him to feel that one doesn't think he is learned or religious enough to be a rabbi. Or, in a community where nearly everyone grew up religious it might cause him to feel like an outsider. So, in answer to your question – there is no clear answer. Certainly it is forbidden to ask such a question if you suspect that the person in question will feel upset at being asked. But, in most cases it is hard to know in advance what a person will feel, and so perhaps the best thing to do is avoid the question altogether. After all, if he's a rabbi, why not take the opportunity to ask him a much more interesting question, such as “Rabbi, have you got any good thoughts on the weekly Parsha?” Blessings.