By Rabbi Yerachmiel D. Fried

Author’s note: In continuation of the ongoing dialogue between the singer Matisyahu and myself, I offer you his response to my recent column in answer to his questions on prophecy:
Rabbi Fried,
Your last answer was nothing I haven’t heard or tried to believe.
Anyway, I’m not looking for answers.
At this point, questions do a lot more for me then answers.
— Matisyahu
Dear Matisyahu,
As you know, Judaism does, and always has, welcomed questions with open arms. The entire Talmud, the foundation of all Jewish thought and practice, is filled with questions. Pesach, the celebration of our birth, freedom and peoplehood, features the seder, which begins with the Four Questions, inculcating into the minds of our children from the most tender age that we are a people who ask questions.
Moses presented difficult questions to the almighty Himself, such as “ … my Lord, why have You brought evil upon this people, why have You sent me?” (Exodus 5:22). Abraham, after being told not to slaughter his son Isaac on the altar, brought a difficult question to God: How could He present him with two contradictory commands and contradict His own promise? (See Rashi to Genesis 22:12). God does not get upset with either Moses or Abraham for their questions; He simply answered them.
This is in powerful contrast to most forms of Christianity and many other religions, which at best don’t encourage questioning and, in most cases, discourage questions completely and consider a seeker or questioner to be a blasphemer.
Many who have approached me considering conversion to Judaism cited this as a key motivating factor for their decision to pursue Judaism. They have been put into some level of excommunication or have been shunned by their religious leaders and their families because they have questions and are seeking answers. They have seen in Judaism the exact opposite attitude, one that welcomes the challenge of questions, apparent contradictions and those individuals seeking truth and deeper meaning, even when those questions challenge the very foundations that Judaism is based upon.
A rabbi explaining why the seder begins with questions presents another spin on this. Imagine a Jew has thought of a novel explanation of a verse and told it to two friends. One thanked him for the nice thought; the second was jumping up and down out of joy. The second friend had a question on that verse that was bothering him for years; the new explanation answered his question. This rabbi points out that many times, much more than the question needs an answer, the answer needs a question.
At times we Jews, and I think this is what you are feeling, express our frustration by questioning. I think this can be good, with one caveat. I will illustrate this with a story of a student of the famed dean of the yeshiva world from the early part of the last century, Rabbi Chaim Soloveitchik.
Reb Chaim had a student whom he had heard had later “left the path” of Torah observance. This student was passing through the city of Brisk and, out of respect, went in to visit his former rebbe. When R’ Chaim saw him, he exclaimed, “I heard you … you … you … ” and was speechless. The man said, rebbe it is true, I am no longer observant, because of three questions I have that don’t allow me to observe the Torah, and if the rebbe will answer the questions, I would be more than happy to return.
R’ Chaim said, “I will be happy to answer your questions, but I first have a question. Did you ‘leave the path’ after you were bothered by these questions, or did you first leave and think of the questions later?” After a moments thought, the man replied that he, indeed, thought of the questions after he had already left his observance.
R’ Chaim replied that he cannot answer these questions, because he can only answer a question, not an answer. “Your questions are not questions, rather answers,” meaning, they’re a justification for what he was doing and not a real question seeking an answer.
That is my caveat: Questions can be good on their own right for a time to get our feelings off our chest, but we can’t allow that to go on for too long, otherwise our questions become transformed into answers, and there are no answers for answers.
Rabbi Yerachmiel D. Fried, noted scholar and author of numerous works on Jewish law, philosophy and Talmud, is founder and dean of DATA, the Dallas Kollel, Questions can be sent to him at yfried@sbcglobal.net.