At the store on the west side of Los Angeles, where we live, I tried to talk Ezra out of the velvet yarmulke. The clerk, whose yarmulke said Shlomo and whose name probably was Shlomo, helped me try. But on the topic of a yarmulke that says a name that isn’t his, Ezra was irrational. He didn’t yet understand that letters signify words, which signify identity. On the topic of velvet being an impractical fabric, he was unmoved. Ezra wanted this yarmulke because that is the kind they wear at his school, which is run by Chabad, the ultra-Orthodox movement. Yet we are Modern Orthodox, not Hasidic, and the yarmulkes men wear in our Modern Orthodox community, the yarmulkes my husband wears, are crocheted.

The kind of yarmulke men wear in an Orthodox community signifies the type of observance they undertake, not by law but by tradition. To me, woven yarmulkes like my husband’s mostly signify that we are Zionists; they also indicate that we identify as Modern Orthodox, that we are constantly straddling the tension over what it means to be a religious Jew in the larger secular world. Velvet yarmulkes are favored by more right-wing, ultra-Orthodox Jews, whose religious practice is led by a central rebbe. Though many of these Jews are missionary in their approach, they are also mostly insular, dressing in a certain fashion and eschewing much of the modern world. If you aren’t religious, you might see the velvet and the woven simply as yarmulkes; but to us, they are often indications of great differences.

To me, Ezra’s longing for the velvet yarmulke pointed to the hold his school has over him and how the lessons it sometimes imparts conflict with the lessons I try to impart. As an Orthodox woman who largely objects to the sexism inherent in the tradition, I am braced for the ideologies Ezra and his brother could bring home as they grow older. But I wasn’t braced for Yosef Yitzchak’s yarmulke.

It foreshadowed other conflicts I’ve known were coming. We’d always planned on sending our boys to an Orthodox day school, the kind I’d gone to in New York, after they finish nursery school. These kinds of day schools are familiar to me: Boys lead prayer, there are co-ed classes until kids are separated around age 10, children undertake Torah-related art projects, like cardboard Noah’s Arks and clay Sinais, and the school day ends long after it gets dark, except on Fridays, when dismissal is long before that. Boys in these schools learn that they are considered superior: They recite a prayer thanking God they are not slaves, then they recite one thanking God that they were not created as women.

(In grade school, I remember, we girls would then recite a prayer that comes almost as an apology: “Thank you, God, for creating me as I am.” Which is not the same thing as thanking God for not creating you a man, or thanking God for creating you as a woman. It is a sentence of resignation, not pride.)

As white men, my boys probably won’t need any help to feel privileged or entitled. Why do they need to assert that privilege out loud in prayer? To what extent are ancient prayers like this at the root of inequality, as much as reflections of it? Though the obligation to utter this particular prayer is tenuous, it still remains in morning services around the world. Increasingly, other staple practices of Orthodoxy—allowing only boys to lead services or to become rabbis, teaching boys and not girls Talmud, and even the insistence that girls wear skirts—are being challenged by some Orthodox Jews. When I looked at Ezra in his yarmulke, I wondered: If he can’t be counted on to follow our example by wearing what we want him to wear at age 3, how can we count on him to dismiss these retrograde religious practices at 10?

I have to face the fact many Orthodox schools are going to teach my boys things I don’t want them to learn and that I can’t count on my kids to be revolutionary in their thinking, to disregard that which is unfair or outdated. And though these are problems I have with Orthodoxy on the whole, I go to a progressive synagogue where these issues are addressed often. And the things I don’t like about Orthodoxy, I don’t allow into my home. My kids will see that, but can that compete with what they’re being taught nine hours a day? I am vexed by contradictory questions: What is the message I send my son if I allow people to teach him that girls are not allowed to chant Torah, when I don’t believe this is mandated in the Torah? Am I teaching him to disregard teachers’ authority? I believe the laws of public and women-led prayer are due for an overhaul. I believe women should be rabbis—and I believe the confines of Orthodoxy allow for these innovations. But am I living these beliefs if I tell my boys what I think and then send them to a school that insists otherwise?

How do you decide what school to send your kids to? When there is no institution that matches your values completely, do you give up on the religious values, or do you give up on your own values? These are the questions Yosef Yitzchak’s yarmulke brought up for me.

For now, we have opted to send Ezra to a public school next year. The decision was based on a different kind of value: financial responsibility. As much as religion is something we cherish, so is the lesson that our children should not spend what they don’t have.

As it turned out, as quickly as Ezra started wearing his new yarmulke, he stopped. A few weeks after his third birthday, he wouldn’t wear it to shul, to school, or anywhere. He took it off and has refused to wear another one since. He just turned 4, and his head, for the most part, remains bare.

I should have known from the beginning that the control I think I have over my child, the influence I think his teachers have, is all an illusion. Maybe school doesn’t matter as much as I think it does. Ezra will grow up, with God’s help, and his head-covering will not be subject to my opinion anymore. I will teach him now what I want him to know and hope that he makes decisions that are right, hope that he doesn’t dismiss our values. He will survive what we teach him; he will figure out what we don’t. We pour our love and knowledge and ethic into him, and we watch with wide eyes to see what comes out slowly over a lifetime. He is as God made him.

Hoffman is also the deputy editor of Nextbook Press, the book imprint affiliated with Tablet Magazine. He joined Vox Tablet host Sara Ivry to talk about the book, how his two careers—novelist and editor—influence one another, and his own experience finding acceptance as a gay Jew. [Running time: 16:09.]

This was a new one for Seidler-Feller, who has built a thriving practice as the go-to sex therapist for L.A.’s sizable Orthodox population. “It was stark, and it was revelatory, and it was disturbing,” she said.

A silver-haired Modern Orthodox Jew who does not wear a sheitl, or a wig, as many of her patients do, Seidler-Feller, 62, says she aspires to make a “cultural dent” in the cloistered world of Judaism’s most pious adherents. “There’s a little bit of the messianist in me,” she said in an interview from her airy office in L.A.‘s Westwood neighborhood.

To help understand this particular patient’s fears, she turned to her rabbi—who also happens to be her husband of 35 years, Chaim Seidler-Feller, the longtime head of UCLA’s Hillel. He found the passage to which the patient was referring in the Kitzur Shulchan Aruch, the 19th-century abridged tome of Jewish law that is widely used as a guidepost for Orthodox Jews on matters of intimacy.

“Clearly the Shulchan Aruch preserves a point of view that is medieval about the fears that existed at that time—and up until Freud’s time—about the vagina and what its powers are,” said Seidler-Feller, the accent of her native South Africa still prominent. “But the point is that it was alive today, in this room.”

What also struck Seidler-Feller, whose work with Orthodox couples comprises about 40 percent of her clinical-psychology practice, was that the notion troubling that married patient derived from a minority rabbinic opinion. That the opinion has survived in the commentary alongside the far more permissive majority opinion written by the 3rd-century rabbi, Yochanan bar Nafcha, vexes her.

But Seidler-Feller’s clinical work can only reach so many, as she says, and several years ago, she and her husband decided to go on the road. At Jewish learning conferences such as Limmud, they unpack what Judaism has to say about sex, with Rabbi Seidler-Feller exploring the textual sources and Dr. Seidler-Feller providing the psychological context. “We want to show people that the majority opinions are permissive with respect to marital sexuality,” she said. “And not only permissive, but instructive.”

The child of a Czech Auschwitz survivor, Seidler-Feller was raised in a nonobservant home where the memories of the Holocaust were palpable; her mother had lost both of her parents, as well as her first husband, by the time she turned 18. Her mother’s tragic past, coupled with her parents’ early divorce, led Seidler-Feller to pursue a career in psychology. “When you have experiences that fracture you psychically, you can try to deal with them in many ways,” she said. “One is writing novels, and another is becoming a psychologist.” At the same time, she said, the traumatic events of her childhood led her to seek out traditional Judaism. By the time she met her husband in 1973 at Ohio State University, where she was pursuing a doctorate and he was the new Hillel rabbi, she had already traveled to Israel and immersed herself in Jewish study.

In her office, decorated with unassuming flower prints—she’d removed a Gauguin print that featured a nude figure after an ultra-Orthodox man complained—Seidler-Feller explained that about 15 years ago, she began to think of Orthodox Jews, particularly the ultra-Orthodox, as culturally underprivileged; she likened it to the digital divide.

“It makes my heart sad that, in the modern world, with all that we have available to us, the sort of information that could so enhance the quality of their lives is unavailable to them because nobody is doing the active translation that is required,” she said.

When she completed the UCLA human sexuality program in the late 1970s, the Orthodox population was far more skeptical of psychotherapy than it is today. Moreover, the field of psychotherapy was far less attuned to religious sensitivities. As a woman steeped in both traditional Judaism and modern psychotherapy, Seidler-Feller realized that she could provide the necessary cultural mediation.

Ultra-Orthodox communities—among them the Chabad-Lubavitch and Satmar Hasidic sects—provide virtually no sex education until couples are about to marry. Even that information, generally dispensed to women by a kallah teacher, who is charged with teaching brides about intimacy, can be minimal. With limited or no access to books and movies, let alone the Internet, community members have few places to turn for information on the most basic aspects of human sexuality. Real-world experience is also limited: The rules of conduct known as Shomer Negiah prohibit girls and boys from touching, while boys are taught at puberty that masturbation is a grave evil.

A 2004 survey of 380 married Orthodox women in New York and Israel conducted by a team of psychiatrists and sexual health experts found significantly higher levels of sexual dissatisfaction among that community than among the general American population. Nine percent of Orthodox women reported never experiencing an orgasm during sex, as compared with 1 percent in the general population, according to a 1999 study on sexual dysfunction in the United States. Tellingly, women who were raised observant were twice as likely to have difficulty climaxing than ba’alot teshuva, or women who were raised secular and chose Orthodoxy later in life.

One of the study’s co-authors, Dr. Michelle Friedman, a psychiatrist who directs the pastoral counseling program at New York’s Yeshivat Chovevei Torah, a Modern Orthodox rabbinical school, said that part of the problem is lack of education. “There tends to be a kind of wariness about sex education and sexual matters in general,” she said of the Orthodox world. “Coupled with the deep commitment to modesty, it becomes difficult to construct appropriate educational models.”

An Orthodox couple will more than likely wind up in Seidler-Feller’s office if they’re having trouble conceiving, unlike secular couples who often seek treatment because they’re not enjoying sex.

Seidler-Feller is herself still fairly conservative when it comes to sex, more Michele Bachmann than Dr. Ruth when discussing pop culture. “The more vulgar our culture becomes about sexuality, especially female sexuality, the more recessed that world becomes,” she says, speaking of the ultra-Orthodox community. “And that’s a dynamic I regret.” It also means that the need for her services isn’t going away anytime soon.

CORRECTION, June 22: Yeshivat Chovevei Torah did not grant quasi-rabbinic status to a woman. This error has been corrected.

I had been raised to fear debt. My mother had made the mistake of cosigning credit card applications with my father when they were married. They divorced when I was 8, he left Brooklyn for Florida, and my mother got stuck with his bills when he was unable to pay them. My mother, a New York City public school teacher, raised me and my sister alone. Throughout my elementary-school years, our dinners were constantly interrupted by calls from my father’s creditors. Now I almost always pay off my monthly credit-card balances in full and carefully budget for all expenditures. Yet no amount of frugality could decrease the amount I owned to the educational-loan company. As the end of my most recent renewal approached, there was only one place I knew I could turn—my nuptial fund.

By all rights, this money should have already been spent. In the Orthodox community where I grew up, girls my age are married, in which case they are called women. I recently attended my 10-year high-school reunion, and I could count the number of singles on one hand. (And a few of the unattached were divorcees.) The rest of my former classmates had already begun constructing a bayis ne’eman b’Yisroel, a faithful home in Israel, as we had been taught to do in our all-girls yeshiva. I still lived in a studio apartment.

So, the money my mother had set aside for my wedding was still there. That she was able to squirrel away a small yet significant sum of money to pay for the hoped-for ceremony and party on her public servant’s salary and eventually, pension, was impressive and a sign of how much my marrying mattered to her.

I only knew about the money because my mother, in the tradition of older folk, likes to speak about her will. She turned 70 in August, but she has been engaged in this sort of talk since I was in grade school. When I was little and used to light the Sabbath candles with her on Friday night, she’d point to the two brass candlesticks and say, “These will be yours in 120 years.” (Since Moses died at the age of 120, many traditional Jews believe that he set a life-span precedent and people cannot live beyond this age.)

The first time she brought up the wedding money, I was 15, and we were in the car driving to school. “I need to speak to Shloimie,” she said. Shloimie is her nephew and a lawyer and is therefore the family repository of legal advice. “I need to add a clause to my will so there will be money so you can have a wedding as nice as Lisa’s.” My older sister, nearly eight years my senior, had just gotten married, and the affair, while hardly posh, was attended by 200 friends and family.

“Uh-huh,” I answered nonchalantly as I stared out the window. I didn’t like what she was implying—that she wouldn’t be around for my wedding as she had been for my sister’s.

Since then, my mother has brought up the wedding clause many times. I usually brush off her mention of final arrangements by saying, “You’ll be annoying the crap out of me for many years to come.” This makes her chuckle.

Yet knowledge of it is burrowed deep in my mind. I’ve often wondered: How much money had she set aside? Could I ask for some of it?

This past summer, I couldn’t stop thinking about the fund. Why did I have to wait until I got married? What if I never got married? If the point of this money was to increase my happiness by giving me the wedding of my dreams—well, I had other ideas about what would make me happy. I kept repeating these arguments to myself until I almost believed them.

The truth was that I didn’t actually want to give up my wedding. Although I’ve never been the type to fantasize about a dress or flower arrangements, I always thought I’d have a wedding. And I thought it would’ve happened by now. Even as I dropped the trappings of Orthodox observance, I didn’t completely let go of getting married altogether.

I entered my late 20s still single and without a significant relationship under my belt. I might never get married, I realized, and there is nothing I can do about it. My career, on the other hand, is something I can make happen. Even in today’s dismal media marketplace, I can network, hustle, and work several jobs into the wee hours of the morning. But I couldn’t force the universe to introduce me to the right man, and I couldn’t force that man to tolerate me. When I thought about where the money would have the greatest impact on my life, I decided that funding my education and career was a sounder bet than a wedding that might never take place.

Last summer, I asked my mother to meet me in my neighborhood. After my mother parked her car in front of my building, we walked to a local café. It was a muggy August day; I was going slow, but my mother was moving even slower. I realized, as I had been realizing many times over the last few years just how old my mother was getting. If at 15, I nonchalantly believed my mother would be at my wedding, I wasn’t as confident at 27.

At a popular hipster hangout we settled into the lumpy couch with our coffees and desserts. I sat silently for a few minutes, staring at artwork on the walls. I was suddenly nervous. I hadn’t planned how to broach the subject. There hadn’t seemed a point to rehearsing.

Finally, I simply asked. It’s hard for me to remember my exact words, but I muttered something about money and a wedding, and said, “I’d like to pay off my school debt.”

Her face fell. “You’re not going to get married?” she asked me, her lower lip quivering.

I tried to reassure her, even though I too was uncertain. I looked down at my dry scone, wondering why I had even bothered ordering it.

I tried to remember all the reasons I had decided to bring this up. I began speaking: It was a good financial decision for her, I said. Costs are only going up. It’s better to pay for a “wedding” in 2010 than in 2012 or 2015. Also, my mother has always been supportive of my career goals. She understood that by alleviating some of the financial burdens caused by my education debt, I could spend more time writing. And finally as a woman who married late herself—at 31, which was and still is ancient in the Orthodox Jewish community—only to get divorced 18 years later, I think she recognized that the wedding is, in the end, just a party. It can make you happy for just one night whereas student loans can make you unhappy for decades. (In that respect, education debt is like a bad marriage.)

As I finished stating my case, she nodded slowly. I wasn’t sure if she agreed with my points or was acquiescing to my request. She gradually conceded that a big, fancy wedding didn’t fit my personality profile. “I always saw you getting married barefoot on a beach somewhere anyway,” she said, brightening up.

We entered final negotiations in the café. The number we settled on was based on the amount she paid for my sister, nearly eight years my senior, to get married, adjusted for inflation since she wed in 1998. I was insistent on this point since I had been fooled as a child when the discussion was about my mother’s contribution to my college tuition. “I will pay just as much for you to go to college as I did for your sister,” she had said. This seemed perfectly fair and generous to a 7th grader. It wasn’t until I was a senior in high school that I realized that I got the raw end of the deal. “But tuitions are much higher now than when Lisa was in college,” I told my mother.

“That was our deal,” she would remind me, shaking her head.

Despite my shrewdness this time around, my mother still low-balled me. “I’m keeping a few thousand dollars,” she said, writing a figure on the napkin. “Because when you do get married, I still want to throw you a small party.”

I almost objected to this change but then thought better of it. She didn’t owe me the money. She finished raising me a long time ago, and all of it was a gift. I kissed my mother on the cheek. I liked that she was still planning my wedding, that she was holding out hope that I will eventually find love with a kind and supportive man, even if I don’t believe it will happen for me. Her faith restored a little of my own. As I walked home, I envisioned professional success, a steadier income, and monetary solubility. Maybe, I thought, I will get to use some of this money for my own wedding. Maybe.

In addition to its annual conference, AJOP is hosting a special kiruv conference for women in the movement this week in Ohio. Miriam Lowenbraun, the wife of AJOP’s director, Rabbi Yitzchok Lowenbraun, has been working in kiruv since she was a child—her father was a rabbi—and her home now is ground zero for her husband’s recruitment efforts.

Ever mindful of the need for outreach, as I interviewed Lowenbraun, she suggested that I listen to rabbinic lectures on tape, recommended a fashionable rebbetzin with whom I might connect, and invited me to spend a Shabbat in Baltimore with her family.

Why have a separate convention for women? Do they have unique issues in their kiruv work?

Women face different challenges. Men are outwardly focused in the community, and women focus on their homes and bringing people into them. In most communities, the homes are the center of operation; you invite people for Shabbos, and people make connections there. Your home becomes the example of what a Jewish, Torah observant, home should be like.

A woman has to balance what’s going on in terms of the people coming to her home and her family’s needs. How do you balance the Shabbos table where you have guests who may need one thing and your own children who need attention?

Women also have to figure out how to present themselves as Orthodox and within the confines of Torah, but still be relatable, with it, and modern. In terms of physical appearance, how do you look good, but maintain the traditional Torah guidelines as far as how one dresses? Also, women have to know what’s going on in the world if people are coming into their homes and having discussions, and for women who are involved with children and daily issues, it’s more of challenge than it is for the men who tend to be more academically oriented.

What are the current issues generally that people working in kiruv face?

Assimilation is tremendous. And in our time it is very hard to find Jews; at one time you could identify Jews even if they weren’t religious because they were involved in a synagogue to some extent. Now there are people who don’t even know they are Jewish, people for whom Yom Kippur doesn’t even enter their life space. And there are many people who think they are Jewish who are not, people who may not be Jewish because their mother may not be Jewish. There are many people in America for whom it’s not an issue—they are so distant already from Judaism. And we are losing kids from Orthodox homes; this is a growing issue that needs to be addressed.

Why is kiruv important—if we all follow our own path, why must it be one of observance?

It depends on what your values are. If I believe that Torah is the core of all existence, and surely of all Jewish existence, and it’s the best life for Jews, and there are Jews who don’t even know the Torah exists, it’s incumbent upon me to reach out and expose them to it. What if someone told you you had a diamond in your family and you never saw it, why would you believe it? It might be hearsay. But if you saw it, you might have different attitude. If I know I have such a special treasure and I love my fellow Jew why would I not want to at least show them the diamond and if they choose to examine it they can? You don’t have free choice if you’ve never seen it.

Is kiruv something that has always been a part of Jewish life or is it a modern phenomenon?

As long as there have been Jews there have been Jews who have strayed, and the community has tried to reach out for them. In the 1700s and 1800s, the Haskalah, an anti-religious movement, tried to emancipate Jews intellectually, and it created a lot of problems, although I don’t think they were on the scale they are today. The phenomenon of losing Jews is not a new one, but the way we try to be more organized in how we reach out to people is a more modern thing. Technology has a lot to do with it. The world has become so small, and the recognition of the problem is better. During the Haskalah there were a lot of Jews who left Orthodoxy too, but they didn’t know about it everywhere. Now you know everything going on the minute it happens.

People are more aware of what the problems are, and there’s a concerted effort to address those problems in a more organized manner. Places like Etz Chaim in Baltimore are exclusively kiruv centers geared to reaching out and making classes available to people who are not affiliated. I don’t know that there were places like that before. The yeshiva movement began in Lithuania as a way to try to stem assimilation and help Orthodox Jews remain attached to Torah. But the biggest yeshiva in Europe had maybe 400 students, and now we have yeshivas with thousands.

I guess Facebook falls into that ‘more organized’ category. At the Women in Kiruv conference, there are two sessions about it.

They’re about how to use the technology for reaching out. It’s not about the halacha or hashgacha of using Facebook, but just practical.

But there are some people who don’t want to go on Facebook and don’t want to be open to just anyone, so AJOP also has their own internal Facebook-style program on our website for people to create their own groups without having to be exposed to the world.

Is kiruv different from the proselytizing other religions undertake?

We don’t missionarize [sic], we reach out to people. A missionary wants someone to be just like they are and do what they do. Outreach opens a door to Torah for people, but everyone has to find their own way in. No two people’s contribution is alike; everyone is unique, and missionaries want everyone to be the same and want everyone to believe in their thing. Other outreach groups reach out to all different religions and want everyone to become their religion; we believe that everyone in the world over can reach G-d in their own way. We only reach out to Jews.

You say that people involved in kiruv don’t necessarily want everyone to be like them, but there are some limits. Professionals in kiruv never encourage women to become rabbis for instance.

Many times people will come from an unaffiliated background, and their first step is towards Conservative Judaism. When people are trying to explore what Torah is, they go through different stages. Personally, as an outreach person, I would like people I reach to connect in their own way, at their own time, and to connect in an authentic way. Everyone has his or her own process of growth and timetable. Everyone has to find their own way and develop their own relationship to G-d. Torah is a process—it’s the work and the process that’s important. Some people think you are trying to make people frum and make people over, but that’s not the goal of authentic outreach; the goal is to be a resource on everyone’s individual journey.

Samantha M. Shapiro is a writer based in New York City.

The term, referring to unobservant Jews who adopt the strictures of Orthodoxy, represented, to us tanned and ignorant teenagers, some cosmic hazard that resided far beyond the reach of our drug-addled universe. We fierce fornicators, we ravers and surfers, just couldn’t fathom how anyone might abandon our raucous ranks, put on the black hat and coat, and forgo life’s profane pleasures, the pursuit of which was as close as most of us had ever gotten to the purpose-driven life.

And yet, abandon us they did, a dozen of them at least, off to ultra-Orthodox enclaves in Bnei Berak or Jerusalem, off to a different life that seemed to suck them away like a dark vortex. The most traumatic departure was that of an older friend, a hazel-eyed chap two years my senior. After learning that he had become religious, we came to think of his past attributes as tombstones for a life he would never again have, tucked away in some yeshiva on a dusty hill somewhere in the south. No more basketball. No more weed. No more trips to the Kinneret with some girl he’d met only the week before, skinny-dipping before slipping into the same sleeping bag, wet with sweat and sex and wild with hope. Instead, our friend was studying Torah, which, to us, meant that he was drying out the flower of his free will between the pages of an ancient and largely irrelevant book.

I thought about my ba’al teshuva friend years later, when I myself began giving Judaism some serious thought, and was amazed and a touch horrified that, back then, I saw his spiritual odyssey as nothing but a long day’s journey into night. I was 19, and religion’s emotional and intellectual depths were invisible to me, like pockets of cool water lying still beneath a thin layer of ice. All I could see were the negations, the denials, the unbearable yoke of religious adherence. Mercifully, that has since changed, and the transformation from valiant son of the Enlightenment to keeper of the faith now represents not surrender but a path along which one is free to travel as far and as stridently as one pleases.

Such, I believe, is the spirit of this week’s haftorah. “This people I formed for Myself,” says Isaiah, channeling the voice of God. “They shall recite My praise. But you did not call Me, O Jacob, for you wearied of Me, O Israel. You did not bring Me the lambs of your burnt offerings, nor did you honor Me with your sacrifices; neither did I overwork you with meal-offerings nor did I weary you with frankincense. Neither did you purchase cane for Me with money, nor have you sated Me with the fat of your sacrifices. But you have burdened Me with your sins; you have wearied Me with your iniquities. I, yea I, erase your transgressions for My sake, and your sins I will not remember.”

It’s a beautifully haunting passage, because at no time does it mention that staple of Western thought, causality. The people sin grievously, yet God gracefully forgives. Isaiah uses no conjunction, no grammatical hook to connect the two sentences together. He simply states: You wearied me with iniquities; I erase your transgressions. Seemingly, no action is required on the part of us humans. Forgiveness comes gratis, compliments of the Almighty.

That, of course, is not the point of prophesy. Isaiah, like his fellow holy orators, speaks in the hope of propelling the people toward purity. He demands repentance, rebirth. But the passage is illuminating nonetheless, suggesting that in Judaism, unlike its sister monotheistic religions, salvation doesn’t necessarily depend on prior action. Salvation comes first; what you choose to do with it is the whole point.

Where does that leave us? How do we go about living when we’ve already been forgiven for our sins? Strangely, that might make our spiritual load even heavier. The burden of proof is always on us. Ours is not a system of penalties and rewards; ours is an endless run toward a goal no human being can ever achieve, namely being entirely worthy of God’s compassion. But that doesn’t mean we should ever stop running. Somewhere along the way, we become righteous.

Each one of us, then, is a little bit of a ba’al teshuva. We may not, like my childhood friend, exchange Madonna for Maimonides, but whether consciously or not, we never forget the true nature of our relationship with God. He, we know, doesn’t need our sacrifices. He, we’ve read, has already forgiven us our worst behavior. In charity, in ritual, in kindness, we all repay the favor.

Hadeish Yameinu by David Gelernter

David Gelernter, a prominent victim of the Unabomber, is a Yale computer science professor who is also fluent in the history and practice of Judaism. An observant Jew, Gelernter just published Judaism: A Way of Being (Yale University Press). Partly an exploration of the religion’s core themes and partly a defense of adherence to its commandments, the book is also an impassioned and provocative plea for Jews to recognize their religion’s unique relationship to God and to Western civilization. Gelernter spoke to Vox Tablet host Sara Ivry about the importance of separation to Jewish life, about Jewish superiority, and about why Conservative and Reform Judaism appear doomed to failure.

The period when my sister was discovering religion was just about the most depressing time in the history of Israeli pop. The Lebanon War had just ended, and nobody was in the mood for upbeat tunes. But then again, all those ballads to handsome young soldiers who’d died in their prime were getting on our nerves too. People wanted sad songs, but not the kind that carried on about some crummy unheroic war that everyone was trying to forget. Which is how a new genre came into being all of a sudden: the dirge for a friend who’s gone religious. Those songs always described a close buddy or a beautiful, sexy girl who’d been the singer’s reason for living, when out of the blue something terrible had happened and they’d turned Orthodox. The buddy was growing a beard and praying a lot, the beautiful girl was covered from head to toe and wouldn’t do it with the morose singer any more. Young people would listen to those songs and nod grimly. The War in Lebanon had taken so many of their buddies that the last thing anyone wanted was to see the others just disappear forever into some yeshiva in the armpit of Jerusalem.

It wasn’t only the music world that was discovering born-again Jews. They were hot stuff all over the media. Every talk show had a regular seat for a newly religious ex-celeb who made a point of telling everyone how he didn’t miss his wanton ways in the least, or the former friend of a well-known born-again who’d reveal how much the friend had changed since turning religious and how you couldn’t even talk to him any more. Me too. From the moment my sister crossed the lines in the direction of Divine Providence, I became a kind of local celebrity. Neighbors who’d never given me the time of day would stop, just to offer me a firm handshake and pay their condolences. Hipster twelfth-graders, all dressed in black, would give me a friendly high five just before getting into the cab that would take them to some dance club in Tel Aviv. And then they’d roll down the window and shout to me how broken up they were about my sister. If the rabbis had taken someone ugly, they could’ve handled it; but grabbing someone with her looks—what a waste!

Meanwhile, my lamented sister was studying at some women’s seminary in Jerusalem. She’d come visit us almost every week, and she seemed happy. If there was a week when she couldn’t come, we’d go visit her. I was fifteen at the time, and I missed her terribly. When she’d been in the army, before going religious, serving as an artillery instructor in the south, I didn’t see much of her either, but somehow I missed her less back then.

Whenever we met, I’d study her closely, trying to figure out how she’d changed. Had they replaced the look in her eyes, her smile? We’d talk the way we always did. She still told me funny stories she’d made up specially for me, and helped me with my math homework. But my cousin Gili, who belonged to the youth section of the Movement Against Religious Coercion and knew a lot about rabbis and stuff, told me it was just a matter of time. They hadn’t finished brainwashing her yet, but as soon as they did, she’d begin talking Yiddish, and they’d shave her head and she’d marry some sweaty, flabby, repulsive guy who’d forbid her to see me any more. It could take another year or two, but I might as well brace myself, because once she was married she might continue breathing, but from our point of view, it would be just as if she’d died.

Nineteen years ago, in a small wedding hall in Bnei Brak, my older sister died, and she now lives in the most Orthodox neighborhood in Jerusalem. She has a husband, a yeshiva student, just like Gili promised. He isn’t sweaty or flabby or repulsive, and he actually seems pleased whenever my brother or I come to visit. Gili also promised me at the time, about 20 years ago, that my sister would have hordes of children and that every time I’d hear them talking Yiddish like they were living in some godforsaken shtetl in Eastern Europe, I’d feel like crying. On that subject too he was only half right, because she really does have lots of children, one cuter than the other, but when they talk Yiddish it just makes me smile.

As I walk into my sister’s house, less than an hour before Shabbat, the children greet me in unison with their “What’s my name?”, a tradition that began after I once got them mixed up. Considering that my sister has eleven, and that each of them has a double-barreled name, the way the Hasidim usually do, my mistake was certainly forgivable. The fact that all the boys are dressed the same way and decked out with identical sets of sidelocks provides some pretty strong mitigating arguments. But all of them, from Shlomo-Nachman on down, still want to make sure that their peculiar uncle is focused enough, and gives the right present to the right nephew. Only a few weeks ago, my mother said she’d been talking to my sister, and she suspects it’s not over yet, so that in a year or two, God willing, there’ll be another double-barreled name for me to memorize.

Once I’d passed the rollcall test with flying colors, I was treated to a strictly kosher glass of cola as my sister, who hadn’t seen me in a long time, took her place on the other side of the living-room and said she wanted to know what I’d been up to. She loves it when I tell her I’m doing well and that I’m happy, but since the world I live in is to her one of frivolities, she isn’t really interested in the details. The fact that my sister will never read a single story of mine upsets me, I admit, but the fact that I don’t observe the Sabbath or keep kosher upsets her even more.

I once wrote a children’s book and dedicated it to my nephew. In the contract, the publishing house agreed that the illustrator would prepare one special copy where all the men would have yarmulkes and sidelocks, and the women’s skirts and sleeves would be long enough to be considered modest. But in the end even

that version was rejected by my sister’s rabbi, the one she consults on matters of religious convention. The children’s story described a father who runs off with the circus. The rabbi must have considered this too reckless, and I had to take the “kosher” version of the book—the one the illustrator had worked on so skillfully for many hours—back to Tel Aviv.

Until recently, when I finally got married, the toughest part of our relationship was that my girlfriend couldn’t come with me when I went to visit my sister. To be completely honest, I ought to mention that in the nine years we’ve been living together, we’ve gotten married dozens of times in all sorts of ceremonies that we made up ourselves: with a kiss on the nose at a fish restaurant in Jaffa, exchanging hugs in a dilapidated hotel in Warsaw, skinny-dipping on the beach in Haifa, or even sharing a Kinder egg on a train from Amsterdam to Berlin. Except that none of these ceremonies is recognized, unfortunately, by the rabbis or by the state. So that when I would go to visit my sister and her family, my girlfriend always had to wait for me at a nearby cafe or park. At first I was embarrassed to ask her to do that, but she understood the situation and accepted it. As for me, well, I accepted it—what choice did I have?—but I can’t really say I understand.

Nineteen years ago, in a small wedding hall in Bnei Brak, my older sister died, and she now lives in the most Orthodox neighborhood in Jerusalem. Back then there was a girl that I loved to death but who didn’t love me. I remember how two weeks after the wedding I went to visit my sister in Jerusalem. I wanted her to pray for that girl and me to be together. That’s how desperate I was. My sister was quiet for a minute and then explained that she couldn’t do it. Because if she prayed and then that girl and I got together and our togetherness turned out to be hell, she’d feel terrible. “I’ll pray for you to meet someone that you’ll be happy with instead,” she said and gave me a smile that tried to be comforting. “I’ll pray for you every day. I promise.” I could see she wanted to give me a hug and was sorry she wasn’t allowed to, or maybe I was just imagining it. Ten years later I met my wife, and being with her really did make me happy. Who said that prayers aren’t answered?

Translated by Miriam Shlesinger.

My joyride through semi-secular Israel came to an abrupt end when, as I entered the 12th grade, my family moved back to the States, land of outlandish opportunities that wove themselves almost immediately through my really-still-pretty-cautious life. Even cutting loose in Tel Aviv, I had kept to the slacker fringe of the tradition-bound, sheltered from truly insubordinate humanity. But here I was, discovering myself on the giant blank slate of a country I knew next to nothing about.

Possibly I got more than I bargained for—or is it less? It had never been my goal to reinvent myself from the ground up. In all my thirst for personal liberty, never would it have occurred to me to shuck my heritage, only to move into its loosest folds. Nathan Englander once commented in an interview on his delight at discovering in Israel the “culturally Jewish” way of life. A Jew can embrace his or her culture anywhere, but in Israel it seems to embrace you, as if it were the climate: holidays blowing in with the seasons, history pumping through the language. In America, holding on to your identity requires commitment. Sporadically, I seek out prayer services, Israeli singalongs, and other establishments of communality and continuity as would have once aroused in me only a great desire to get out. But for a system of observance, to perform my personal rituals of worship and irreverence, love and skepticism, gratitude and frustration, loyalty and dissent, I rely on the discipline of writing.

The notion of narrative as stopgap, a tent city filling the void left by dismantled conventions, occurs out of driving need, I think, to writers like Englander, Pearl Abraham, or myself, who may always be digging in the scrap heaps of their deconstructed Orthodoxies for building materials. From an act of destruction we try to yield a construction, from the bereavement of voluntary loss a life of compulsive creation, from rebellion a sort of community service. It is curious—or else entirely understandable—that a towering originator of our destructive and preservative guild did not himself emerge from the Orthodox world.

Philip Roth, 1960.

When I consider Philip Roth’s work in this light, I imagine a troika of fictional characters harnessed side-by-side to pull their precarious shared load, massive and complicated and tending to disjoin. There stands Sergeant Nathan Marx, “Defender of the Faith,” powerfully built although beginning to develop a paunch, doubt in his eyes, discipline fixing his jaw. Beside him rangy, off-rhythm Alex Portnoy, complaining, painfully aware of what they say he should be pulling, but just as fixated on bulges in the pocket. Finally, the author’s newest creation, the 7-year-old Phil Roth of The Plot Against America. On first glance, the small boy seems to emulate precociously the methodical sergeant, to whom he glances for cues. Watch him closely, though, and you will see that every now and then this sober kid, wide-eyed with sudden terror, tries to slip the reins and bolt. In the manner of Biblical archetypes from Abel to Joseph, each reflects the same idea reconsidered.

At a 1962 Yeshiva University appearance, Roth was assailed by an angry mob of faculty and students for what they saw as his calumnious depiction of Jewish character in “Defender of the Faith.” In the story, a Private Grossbart asks Sergeant Marx, his coreligionist, for preferential treatment, using Orthodoxy and shrill claims of tribal preservation to support his escalating demands. In his later autobiographical work, The Facts, Philip Roth traces the conception of Portnoy to the YU encounter. With Portnoy, who arrived in 1969, Roth was “upping the ante”; if grabby Grossbart offended, let the YU crowd try the most bawdily voracious Portnoy on for size.

But Portnoy is not an extension of the dishonorable Private Grossbart; he is the literary offspring (or perhaps bastard child) of Grossbart’s nobler foil, Sergeant Marx, who is initially taken in but finally cuts off the favoritism, rescinding Grossbart’s last wangled favor, to be stationed in New Jersey rather than the Pacific war zone. Jew by birth, all-American by ideology, Marx redefines his faith-defending role as a righteous law enforcement, a kashrut supervision of fellow Jews following universal standards of decency and accountability, foreshadowing Alex Portnoy’s high position on the Commission On Human Opportunity. You might say all the opportunity lands Portnoy on the shrink’s couch. You could say also that complaining is his opportunity to populate the gap between all that he feels he could be and have, and what his galloping sense of possibility has actually managed to get him.

Now, in The Plot Against America, this epic complaint—issued by one Roth character after another—finds its youngest agent. Little Phil Roth, “a third grader a term ahead of himself,” does have a certain edge on worldly wisdom, but being so young he’s only dimly aware of all that lies beyond the low-cut hedges of his neighborhood and the shelter of a loving family. Through his philately, Phil discovers the arrhythmic pulse of the American promise, stamp by stamp: Horace Mann, America’s early champion of education as the Great Equalizer; Booker T. Washington, “the first Negro to appear on an American stamp”; Susan B. Anthony. But there is no black face on a stamp celebrating American children, and no stamp portraying a Jew.

Readers can see a better future and the pluralistic stamps honoring Hanukkah, Eid, and Cinco de Mayo. But Phil is living in an alternate past, which may not be headed our way. In times overtaken by a warped spirit of progress, Charles Lindbergh, conqueror of the Atlantic skies and proponent of Hitler, has risen to the Presidential post. Phil’s quandary is not so much how to reconcile his will with his roots, but how to keep the basic package alive.

To Marx and Portnoy, tradition-bearers are challengers, will-suppressors. Phil, by comparison, has never felt tradition as a threat. A moderate Jewish ritualism has always figured into his life, as reassuring as the measured rhythms of his dedicated parents’ daily labors. Phil’s parents are The Plot‘s brightest lights, mythic guardians and loyal Jews, who even at the height of chaos and despair maintain a valiantly stubborn grip on normalcy. Surely their gosling could never see in them an affliction; without them he would not survive.

This is not any child, though, but a Rothian hero of modernism. Even under the most crushing strictures in the world, his sense of possibility offers innovative options. If his immature psyche cannot articulate his wish to be parentless, his actions speak for themselves. Phil attempts to run away to a Catholic orphanage, but is kicked in the head by a horse, rescued by Seldon, his clingy, fatherless Jewish classmate, and delivered unconscious back to his Jewish fate.

It is Seldon—prototypically brainy, ostracized, luckless—who with his impositions on Phil’s conscience recalls Private Grossbart, minus the villainy. In an eerie channeling of Sergeant Marx, Phil arranges for poor Seldon, like Private Grossbart, to be sent to a war zone, or what soon becomes very much like one: Kentucky, which is overtaken by pogroms.

Marx’s action was a setting-straight of a shirker. Phil’s is something like the opposite, a passing of the buck. His family received the original transfer orders. Thus Phil continues the once-righteous Marxian line. According to the same high humanistic ideals, he attempts to break from coercive script. In compliance with low Portnoyan law, he makes a dirty job of it, and like Portnoy he suffers the consequence. The Roth family takes in the orphaned Seldon and Phil must become, in The Plot‘s final words, “the prosthesis,” trying to fill the dreadful gap that his own striving has caused.

The Facts suggests that Roth was riled by the YU criticism. Yet in “upping the ante” he did not indulge in mere defiance, but went the poker player’s way, taking the match of wits seriously and increasing his own personal risk. Beset by angry big-beards, the universalist took a harder look at his subject: life as he knows it, defining itself outside preset molds. And perhaps it is not so often heroic as it is outrageous and self-crippling, or maybe it’s a child who knows not quite exactly what he does. 5,765 years of tradition and 613 commandments map a tested method, but some kids just have to do it their way.