There’s an odd rule about making kiddish.
Kiddish, for the uninitiated, is a brief ceremony Orthodox Jews observe before Friday night and Saturday afternoon meals in which we commemorate our observance of the Sabbath by making a blessing over wine.
It’s customary to use red wine, so much so that I was taught to pour a little grape juice into white if that’s all you’ve got of a Friday night. But there’s a catch in the winter, at least among the chassidic circles I run in. It’s best, they say, not to make kiddish between 6 and 7 pm, but if you do, you should make it on white wine.
The reasons for this practice are too complex and arcane to summarize in a line or two. (In other words, they are Kabbalistic.)
It’s a rule I’ve largely ignored until recently it was pointed out that a relative kept it, and I started to wonder if I wasn’t neglecting an important guideline. So, I did what I often do: reach out to the nearest rabbi for perspective. And when I say reach out, I mean it almost literally, because in my synagogue, you can’t swing your arm without fear of striking someone with smicha.
I was on my way home from Friday night service, when I buttonholed the nearest clergy and asked him if he held by the rule in question.
“I hold by it,” he said. “But I don’t keep it.”
When I began my long march through Orthodoxy, I had a pretty black-and-white understanding of how things worked.1 You either kept kosher or you didn’t. You either kept Shabbat, or you didn’t. You either believed in Torah, or you didn’t. And if you did any of these things, you probably wore a black suit and hat.
Later, I learned that not all Orthodox Jews dressed the same. Some wore black hats; some did not. Some wore knitted kippahs, some velvet. Some only wore suits, some jeans. The dress code largely depended on your sub-category. In some circles, it was okay for an Orthodox man to wear shorts. In others, you might get rocks thrown at you if you weren’t wearing the right colored socks. To some extent, it was a product of the family you were born into, but for a “baal teshuva” (born-again Jew) such as myself, it was more a product of with whom you chose to worship and learn.2
But even when I discovered there was more flexibility than I thought, I still figured that with regard to halakhah, Jewish law, you were either on board or not—either on or off “the derech”—i.e. the path.
If you were on the derech, I figured you did what you were told. If you were a man, you lay tefillin every morning. If you were a woman, you went to the mikvah once a month or so. Couples slept in separate beds, made love with the lights out, and wore not a stitch of clothing when doing so. Everyone prayed three times a day. You wouldn’t take a sip of water without making a blessing; you wouldn’t take a bite of bread without ritually washing your wands with a two-handled cup; and you wouldn’t get up from a meal or a snack without “bentching”—reciting the after-blessing.3
I knew as a baal teshuva, I wasn’t expected to take on everything at once. Start with keeping kosher and Shabbat and move onward and upward. At some point, I learned the principle of “keeping as high as you can,” meaning that I might not be up for observing all the mitzvahs right now but that I would try to keep as many as I could—with the proviso that one only moved in one direction up the ladder.
So, for example, I stopped using screens and spending money on Saturdays before I stopped driving and turning on lights on Shabbat. I stopped eating milk and meat together before I started buying kosher products. I kept one hour between milk and meat before I started keeping three before I started keeping six.
Along the way, I developed a philosophy that went something like this: I may or may not have questions about the law. I may be skeptical about its underlying assumptions, its raison d'être. But the distinction between what I keep and what I do not is not a matter of doctrine but of what feels right, of what I can take on without hating the rule, or worse, hating Judaism. I go along with the six hours between meat and milk now because I can do so without resentment, not because I agree with the rabbinical reasoning behind the rule (which I do not).4
This has sometimes confused friends. Why do I keep one thing and not the other? Why do I wear tzitzit but not daven three times a day? Why do I refuse to turn on a light but still tear toilet paper on Shabbat?
My answer has been, “I keep what’s either easy or meaningful to me.” I’ve even told my son, “Don’t take on anything that will make you feel more distant from Hashem.” And that’s what I tell myself.
Why do I sometimes go higher, adopt practices I had previously eschewed? I don’t know. Guilt, a desire to be closer to Hashem, a desire to challenge myself, because a rabbi’s speech inspired me, to feel more like a “real Jew,” to fit in with the community, and doubtless manifold unconscious reasons. But simply put, I hold as high as I can, and I believe that’s good enough for God.
But I thought until fairly recently that this sort of “pick-and-choose” Orthodoxy was only practiced by the uncommitted, the Orthodox-in-progress, i.e., the perplexed. Those guys in the black hats, the women in sheitels, they walk the straight and narrow path—until they don’t.
By which I mean, I always knew that sometimes Orthodox people go off the derech, doff the uniform, move out of the neighborhood, start watching secular films, and eating cheeseburgers. But what I didn’t realize was that some Orthodox people follow their own derech.
I got hints of this long ago but couldn’t believe my eyes.
For example, I often thought I saw Orthodox children eating bread without washing. I figured it was just kids being kids, but even so, it was surprising because I assumed they’d been so thoroughly inculcated with the essential nature of the practice that eating bread without washing would be like peeing your pants, something only a toddler would do.
But then I also noticed some Orthodox adults eating bread without washing, even—dare I say it—some with smicha.5
At first, I tried to give such people the benefit of the doubt. Maybe they had washed without my noticing it. Maybe they had washed earlier before I came on the scene. Maybe they had washed before they left the house, knowing it would be difficult to do so later (though I’m pretty sure there’s a halachic issue with that).
But I witnessed this “transgression” so often and in so many circumstances that I could not but doubt it was occurring. Moreover, I noticed that even if they did wash before bread, they often did not bentch afterward, which is also a no-no. In fact, this omission is so common it sometimes seems that those who do routinely—one might say religiously—make the blessing after bread are in the minority.
My point here is not to accuse anyone of hypocrisy but to explain how I gradually realized that the Orthodox are not perfect, that they don’t always do what they’re “supposed to do,” and that, like me, they sometimes “hold by,” i.e., believe in a mitzvah, but, for one reason or another, do not keep it.
The whole thing kind of reminds me of when I first learned that girls fart.
I was raised one of three boys and was a pretty shy boy at that, so I didn’t spend a lot of time around girls before high school, and even then not in the way I did at college.
But long before today’s bathroom wars, there was at Vassar an unofficial policy that men’s bathrooms were essentially co-ed. No one batted an eye if a girl brushed her teeth, showered, or relieved herself in the “men’s room.” It startled me the first time I noticed a pair of panties pulled down around ankles in the stall next to me. But it was a revelation when I first heard the undeniable sound of a female passing gas.
Look, I was an adolescent. I looked at women as at another species, a superior one in most respects. I thought of them much like Sam Gamgee thinks of elves in The Fellowship of the Rings.
“What do you think of elves, now?” Frodo asks him after his first encounter with them.
“They seem a bit above my likes and dislikes, so to speak,” says Sam.
That’s how I thought of girls. Learning that females farted was a step toward humanizing them.6
And, likewise, learning that the Orthodox don’t always do what “they’re supposed to do” was a surprising but liberating lesson for me. It relieved me of the fear that I would have to become someone else, someone not myself, to observe Judaism. It’s given me the room I need to experiment, to fail, to say, “I’m not ready for that, and I may never be,” and yet to think of myself as Orthodox.
Why is that important? Why do I need the label?
Look, I dislike labels as much as the next guy, more so even. I avoid wearing shirts with corporate logos on the front pocket. I don’t put bumper stickers on my car. I’m right there with Kramer refusing to wear the red ribbon.
But I do want to belong to a community. And I have chosen the Orthodox as my religious family and as my authority in matters spiritual. And I don’t want to feel like a fake or a poser.
So, how high am I holding now? What do I keep?
When I began my Sabbatical last semester, I told the higher-ups at my university I was going to be a chassid, a pious Jew—or at least some version of one. I’d daven three times a day with a minyan, study once a week with a chavrusa, participate in a daily study of Mishnah, and learn to lead a service.
In the end, I did none of those things. My study partner and I kept running into scheduling problems. I was bored by Mishnah. I realized I might never learn to read Hebrew fast enough to lead the service. And I just couldn’t convince myself to sacrifice the daily hour to the afternoon and evening service despite my seeming to answer the question, “Why does God make us pray so much?"
I’m pretty sure the UTC administration won’t hold it against me, and I’m not going to hold it against myself.
I did up my game, though. I daven the morning service and lay tefillin daily—except when I don’t, which is not that often. I spend half an hour every day learning something Jewish, which I wasn’t doing before. And I didn’t drop anything I was doing before. So, I’m holding higher than I was, but not as high as I thought I would.
Fortunately, I live in a Jewish community that prides itself on its diversity, not of race or ethnicity, but of practice. There are, undoubtedly, lines one is not supposed to cross around here, but there’s considerable debate about what those are and what it means to test them. Indeed, while I’m trying to figure out how much I need or want to conform to Orthodox standards, many of the religious-from-birth folk7 are trying to figure out how much they can free themselves from those standards and still be part of the community.
To paraphrase Sir William Harcourt, “We’re all perplexed now.”
And so I end this substack with a passage from the work of Sam Gamgee’s creator, lines I quoted in my high school yearbook but which still resonate low these 42 years later.
The Road goes ever on and on. . . .
And I must follow, if I can,
Pursuing it with eager feet,
Until it joins some larger way,
Where many paths and errands meet. . . .
And wither then? I cannot say.
A notion reinforced by the fact that all the Orthodox men I knew dressed in black and white. (I remember once remarking to an Orthodox man about this dress code. He said, “What do you mean? My suit is blue.” I suppose it was, but you had to squint to see it.)
Even so, I ditched my earring pretty early in the process.
The laws are so complex that they are the subject of a 22-hour lecture series I once listened to.
There’s some disagreement in Judaism about exactly how many hours you need to keep. The people I first learned from kept three. The Dutch Jews, I’m told, keep one. But pretty much everyone, push comes to shove, agrees that the standard is six.
There is a legit question here of whether, in writing this, I’m practicing “lashon hara,” evil speech, which is a form of gossip or tale bearing that is strictly forbidden in Judaism. Maybe. But I’m not naming names, and some things need to be talked about and written about. If I strictly followed the laws of lashon hara, I couldn’t even keep this Substack because pretty much twice a month, I write lashon hara about myself, which is also not permissible.
I wonder how Sam would have reacted if he had heard Elrond break wind?



You learn from mentors about how to live what and how to learn and how to raise a family and what a Shabbos and Yom Tov table looks like When you see non compliance with Halacha ( and many BTs have seen it) you have to just do what you know Halacha requires and not pass judgment regardless of what Halacha has requires from all of us as individuals and as a community
What you might have benefited from was a community with like minded role models who could serve as mentors