I am constantly asking my Rabbi questions on my faith or other topics in Judaism. I keep on getting the feeling though, that my questions are being discouraged, and shot down without an answer. Although I thought that Judaism appreciates discussion, I am told that ask these types of questions should better not be asked, and I should rather trust my teachers, parents, and my tradition. I am a bit confused: Is it better to challenge things that I don’t fully understand, or accept unquestioningly everything that I am taught?
Whether or not questions are encouraged or discouraged in Judaism, does seem a little confusing, and I understand why you feel the way that you do.
It does seem puzzling: On Pesach we sit down to the Seder and dedicate the night to asking all the questions that we may have, enacting certain things with the sole intent of getting the children to ask—kdei shyishalu ha’tinokos.
The rest of the year though, we seem to be pushing the opposite agenda and singing a different tune, telling people to have faith without ever explaining the reasons for all the various things that what we as Jews may do.
However, making a blanket statement that questions are either good or bad is impossible. The true answer, like everything else in life, is more nuanced and complex, and not black or white, yes or no.
A good question depends on the way that the question is asked. If the question is posed in the correct manner, it is good, if it isn’t, it may be bad. The same words may be used, but what determines whether what we are asking is good or not depends on our internal mindset and the goal that we are seeking by our query.
To explain: imagine that you come home one day and your father asks you what appears to an innocent question: “What did you do today?” How do you react? Are you touched that he took time out of his day to ask how you are, or do you feel a little upset, or hurt by this question?
The answer is that it depends on the way the question was posed. If your father is genuinely curious and interested in what is happening in your life, you would probably give him a full rundown, sharing with him the ups and downs of your day and the tiniest details of your life. However, if your father is asking it in a critical manner, insinuating that you’ve been up to no good or wasting your time, if his tone of voice implies that you are in trouble, you may clam up, or answer as briefly as possible, and definitely not be as talkative as in the first scenario.
In our daily prayers there is a poem that is entitled “Ain Kelokainu”—there is none like our G-d. In it, we notice something very strange as the poes seems to be in the wrong order! We first say ain ke’lokainu—that there is none like G-d, and then we immediately continue and ask, “mi kelokeinu”—“who is like G-d?” This seems to make no sense! If we just asserted that there is no being like G-d, why are we now asking “who?” We have already answered that a second before?!
This teaches us something very deep, and shows us the manner that we are to ask questions regarding our faith. Before we ask these serious questions we must first preface with what we already know – that there is an answer and the answer is in Torah, and now all we need to do is find it, and understand it.  After this firm foundation, we can now ask and explore.
Much success, in all your questions! I am sure that when you search in earnest, you will find that Torah is geshmak (sweet) and that the answers to all your questions are to be found in the Torah. Dovid Hamelech enjoins us, Tamu U’reuh Ki Tov Hashem—
 ראה בספר טללי אורות, ביאורי תפילה ג, תפ