While it can be alarming to hear such questions, they’re not actually as unusual as many people believe. They’re also not as terrible as people believe, for a number of reasons.
Yiddishkeit has never frowned upon asking questions on virtually any topic. Many sefarim that discuss topics of emunah are based on asking and answering questions. The same is true of the Haggadah. The wicked son is not punished for asking a “bad” question but rather, because he excludes himself from Klal Yisrael. Asking a challenging question does not exclude the person from our nation. In fact, in last week’s parshah we learned that Moshe Rabbeinu did not teach Am Yisrael the laws of Shabbos until they asked about them.
When it comes to replying to such questions, it’s important to realize that there are many ways of interpreting them. There is the literal interpretation: What does the question actually mean? There is a deeper attempt at interpretation: Why is this person challenging me like this? And then there is a personalized interpretation: What does this question reveal about the person asking it?
While taking a literal approach may be best with other kinds of questions, with questions such as the ones posed by this high school boy it is very likely that he did not mean them literally and therefore, taking his words at face-value will not achieve very much. Similarly, treating the questions as obnoxious challenges to your authority as rebbi will likely also backfire.
This is why responding defensively (“How can you ask something like that?”) often gives the impression that you simply don’t know how to reply, and that’s a sure way to lose your student’s respect. Furthermore, it will give the question a heightened importance that it doesn’t deserve. In all likelihood, your student doesn’t want a literal response, but if he senses that he’s “caught” you, he may start to wonder whether he’s somehow stumbled on a deep dark secret that must never, ever be exposed.
What a parent or teacher really needs to do when trying to respond correctly to such questions is to take the third approach, which is to answer the person rather than the words spoken. Here, you have yourself noted that he probably feels stifled and restricted by all the halachos. It’s reasonable to assume that what he is seeking is a way to get past that stifled feeling. Perhaps subconsciously, he’s even looking to find the joy in Yiddishkeit. If you treat him as nothing more than a rebellious teen who just wants to have fun, all he will have learned from the exchange is that seeking answers will only make things worse and that you now look down on him and see him as a “bad kid” — which is the last thing either of you want.
Therefore, your initial response should actually encourage the asking of questions, no matter what they are. If you can also convey that having such questions is a sign that he is someone who seeks wisdom and understanding, that’s even better. And if you can add that you, yourself, had similar questions when you were younger, that’s amazing.
After setting the scene, the next step is to address the question itself. It should be obvious to your student that you welcome the opportunity to delve deeper into this question with him and that you’re happy he asked. This doesn’t mean that you have to know the answer, although you should show confidence in the fact that there is an answer — which is precisely why you’re willing to engage and investigate instead of ignoring or invalidating. You can even admit that you don’t know the best way to respond, and ask for a day or two to think it over, or suggest that the two of you go to consult with a Torah authority if that’s an option.
In the past, I’ve sometimes suggested that fathers take a similar course of action, whenever their child didn’t seem open to an explanation from them. Having them both go together to a rav (who was given advance warning) proved to be a better option and helped them strengthen their relationship.
I once spoke with a chassidishe bachur after discovering that he had attached himself to a somewhat unconventional mentor. I asked him why he had chosen this person as his “rebbe,” and he replied:
“I had all these questions, and no one wanted to answer them. Everyone put me off with one excuse or another. Some of them seemed to look down at me just for asking. Eventually, I found my rebbe, who was not only capable of answering — he was actually happy to answer! So I decided that he was someone who I could follow and admire.”
This mentor probably saved this bachur’s life. Meanwhile, all the people who either refused to answer or didn’t know how to respond gave the bachur the message that his questions weren’t welcome and that he, himself, was a problematic kind of person.
If you’re a person who finds himself challenged by such questions, do what you can to keep the channels of communication open. This way the next time the person needs something addressed, he’ll come looking for you again. The bachur I encountered was fortunate that he found an ehrliche mentor. Unfortunately, some boys who fail to get their questions answered by the right people end up getting them answered by people who put terrible thoughts into their head. They then encourage them to follow up with even more doubts and confused thoughts, and unfortunately lead them very far away from Yiddishkeit.
While these people may sometimes have positive intentions, the one thing that they can never give to confused or struggling people is the sense that they are in Hashem’s loving hands and that there’s no better place to be. So, as you write, what is the best way to convey how much Hashem loves us and how He has given the Torah to us for our benefit? Though it may not be easy to “explain,” just being clear in your mind will make it a bit easier.
You know what you’re not looking to convey; anything that could make him feel threatened or bad. You also know what you are looking to convey, which is the conviction that living a Torah way of life is absolutely beneficial. Nonetheless, I would suggest presenting your thoughts as interesting ideas to think about rather than the rock-solid facts they are.
The reason for this is that pushing ideas onto people doesn’t usually work. Sharing them as suggestions rather than facts to be either accepted or rejected makes it easier for others to listen. People often make the mistake of presenting ideas in a way that forces listeners to either surrender or wage war, which makes it hard for them to admit to what they know is really true.
