We had a bunch of guests over for Shabbos lunch. This was on a summer afternoon, just a couple of years ago. Since my husband hadn’t returned yet from shul, everyone was passing the time in the living room, waiting. There was a relatively new guest, David, seated on the couch, who had only just started coming to us to experience Shabbos. Sitting on chairs across from him, was a couple who had become Orthodox about fifteen years ago, and a few others guests were milling about too.

The couple was discussing something about what the rabbi had said in shul, and David piped in with a question about what the rabbi said. I don’t even remember anymore what the actual topic was. All that I remember vividly is the brief exchange that transpired next.

The wife stated very emphatically that one must never question a Rav. David responded very innocently that he thought that Judaism was a religion that welcomed questions, so rabbis would welcome being questioned. “Aren’t we supposed to question?” he asked, and a stiff silence followed. Nobody responded to David. Not even me. I just didn’t know what to say then. Another guest must have changed the subject, thank G-d, and the conversation in our living room shifted somewhere else. But David’s comment had scooped me up out of the living room, and it got me sailing back through time.

Back to an innocent time of questioning. Over thirty years ago, the wonderful Orthodox rabbis that we discovered – or that discovered us – encouraged the questioning of everything. They taught us that Judaism was all about questioning, and then questioning more, until you reached greater and greater levels of clarity. Keep asking until you find emes, we learned, within the Torah and within yourself. And we thrived on this – this freedom to examine and sift for absolute truth.

No stuffing dogmas down our throats – as in other religions, we learned. No more unconsciously accepting assumptions – as in the subliminally anti-religious mind-sets we hadn’t even realized we’d adopted. Develop delving skills, sift for truth! We were so thrilled to see that the way to study Torah was through questioning. It was open for genuine exploration, earnest close examination, and so were its welcoming teachers.

We loved discovering that wise people learned from everyone. And even though the rabbis and rebbetzins who taught us, had so much more Torah knowledge than we had, they let us know that through our questions, they were gaining new and refreshed perspectives on just about everything. They really helped us understand that we were expanding and deepening their wisdom through our challenging inquiries.

Then I was jolted back to the present. When did the encouragement of questioning stop?

And why don’t we feel safe anymore to question?

I’ve been trying to figure that out ever since.

It no longer tastes like the Torah we were first offered, when those with clout invalidate sincere questioning by dismissing it as being presumptuous.When people only feel unafraid to voice their doubts and questions as anonymous comments on frum blogs, we can be grateful for these opportunities for suppressed voices to be heard, but it also highlights that a fear of speaking up is prevalent. Instead of feeling threatened by these anonymous comments, and seeking to forbid them by imposing bans on these venues, we need more leaders who can garner genuine respect by encouraging as much open questioning as possible. Then they too can actually benefit from the perspectives and challenges presented.

Critical feedback is needed by all of us, if we really want to improve. The man recently caught on video kissing a mezuzah before stealing from a store, can serve as a kind of ridiculous caricature to keep in mind of how far off the derech we have gone, with plenty of our extra stringencies or just mere cultural trappings covering up – from others and even from ourselves – our inner spiritual lacking.

Painful experiences have taught us to fear communal reprisal, arrogant attacks from those who wield power, and mafia-like intimidation tactics within our midst. We discovered that our leaders made decisions based on financial backing and political favors, instead of on pure spiritual motivations. And we found out that this has been going on unquestioned. As we learned a little more Torah that we hadn’t initially been taught, we also came to understand that in the hands of unscrupulous people, Torah can be misused as a deadly poison (Yoma 72b).

Thank G-d, this isn’t supposed to be the religion that promotes viewing its leaders as infallible or even unapproachable. Throughout Jewish history, there has been an ebb and flow of leaders who became mired down by corruption. Power corrupts, and the Torah emphasizes concern, in reference to a Jewish ruler “lest his heart become haughty over his brethren” (Devarim 17:20). The ruling elite can too easily come to place its own preservation above all else, if left unchecked.

Nearly every day I hear from a baal teshuva who has become disgusted by an excessive focus on the superficial aspects of frumkeit at the expense of the intrinsically meaningful aspects that initially drew the individual to yiddishkeit. They describe their disillusionment with the stress on the façade and on sheer phoniness in place of underlying true moral behavior. Many of those who have been burnt by the corruption that has become entrenched, have been slinking away, but that’s exactly what intimidators are trying to achieve.

The ones whose eyes have been opened and the ones whose hearts are full of essential questions, could be just the ones needed most to help us all return to more pure practice.

Yes, we are supposed to question, alright.

Hope you’ll come back someday, David, along with everyone else who left, disillusioned. I’m sorry it took so long for me to have the clarity to answer. Your question really helped.

Originally posted here.
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My personal life calendar operates around the great upheaval through my discovery of Yiddishkeit. If that is “year 1”, then 10BC (Before Change) was my Bar Mitzvah, and 5AD (After Discovery) was when I got married. This being the case, there were other notable events which had far reaching consequences as well. And, like they say, timing is everything.

In 2BC, my father was remarried, this time to a non-Jewish woman. I secretly would have preferred that he marry the Jewish woman he had been dating a few years back, but, alas, he decided this wasn’t to be. (She was quite upset, I happen to know.) Nevertheless, he’s my dad, so I celebrated with him in the Hall on the lake, and I wondered what was going through my grandmother’s mind as her siblings paraded around her. Perhaps it made no difference, since her husband, my grandfather, had done the same thing.

In 1BC, my brother, faithful to the ways of his avos, became engaged to a non-Jewish woman as well. A very nice lady, she was, and I congratulated him on his choice and wished him the best. However, as he was making his plans, my life went on, and the wedding wouldn’t be until 2AD.

In 1AD, my brother announced he was to be wed in a church (they liked the stained-glass windows, they said). Already I had a bad feeling about this, since in 8BC, I attended a cousin’s wedding in a church, and felt quite nauseous while sitting in there. (Perhaps it was that statue on the wall accusingly staring at me.) But now, more than ever, I was quite troubled. When I asked our local posuk about going into a church, he answered that he would think that if an Arab is chasing me with a knife it might be permissible, but probably not. The strong language was so I would get the picture.

In 2AD, life was so confusing. Despite knowing the direction I wanted to go, I still had so much to sort out. Did I really care if my brother married someone not Jewish? Really really? None of the terutzim regarding intermarriage sat well with me at that early stage, but I had to chose a derech…and stick with it. I understood what the rabbis say, and felt they were right, but what about my family?

I told my brother I wasn’t going. He thought I was joking…I wouldn’t be best man at his wedding?? I’ll skip the blood and gore…it was awful. Devastation doesn’t even come close. My father’s blood pressure became a steady 400/200. It was actually a relief when he stopped talking to me (although perhaps five years was overdoing it a bit.) My mother did understand to some extent, but cried anyway. And now, in 20AD, my brother still hasn’t said a word to me, despite numerous attempts to reach out.

My extended family was horrified. I could not help but think that this was some sort of chillul H-Shem, despite the rabbis telling me it was the opposite. But how could that be? What does my family think about orthodox Jews now? They’re not exactly running to their local kiruv center. How could I have answered my father’s main objection: “You danced at my wedding, didn’t you?! What happened since then?” See? Timing is everything.

I was alone. I just threw my family over a bridge. Goodbye family. And did the rabbis understand? I wondered. So there I was at 2AD, thousands of miles away and nothing to say. Looking back, I know that not going was the right thing. I bet, though, that it could’ve and should’ve been handled much differently, but that’s in the past. But what I didn’t know is that my whole experience had a name!