Kayla, an ambitious finance professional, once applied for a position at a top-tier, frum-owned firm. After doing some due diligence, she discovered that single women in the firm were paid less. Determined to snag the higher rate, she borrowed a sheitel for the interview — and secured her target salary.

In other companies, pay is comparable — but certain perks are for marrieds only, like Yom Tov bonuses. “There’s this sense that singles don’t have bills,” Kayla says. “Especially for women who live alone, it’s the furthest thing from reality. They’re in the highest tax bracket because they have no dependents; many rely on weekly therapy — for survival! — and they may be investing huge sums of money in treatments that increase their likelihood of bearing children at an older age.”

On a communal level, singles are perhaps the most untapped resource of talent. While a huge number of single women invest countless hours in chesed and kiruv, often doing jobs few others can, like sleeping long nights at a sick child’s bedside, their expertise is generally overlooked when it comes to leadership positions. In light of the single woman’s (generally) enhanced energy, availability, and often professional knowledge — many have had the chance to invest extraordinary resources in professional development — those who stand to lose most are community members themselves.

“I have friends who are experts in their fields,” Rachel Burnham shares, casually mentioning a Columbia-trained neuropsychologist, Department Head at JP Morgan, and highly-specialized addictions therapist“Why not invite them to present at a conference? Why not ask them to head a committee, or facilitate a workshop at a convention?”

These chesed giants are rarely honored by organizations, even when the dinner is female-only. In a dramatic case, Shaindy, a passionate dynamo who scaled a tzedakah organization from a no-name initiative to a global operation, was politely asked to step aside — and make room for a married woman. “Potential donors will feel more comfortable meeting with a Mrs. than a Miss,” the non-profit’s executives told Shaindy, apologetically asking her to resign.

Mrs. Ruth Daskal,* the woman set to fill her shoes, however, felt entirely unequipped — and expressed her concerns to the board. “There’s no way I can invest the time and energy required,” she said, citing family obligations. The board explained that they were well aware of her limitations. They laid out an audacious proposal: Shaindy would continue doing most of the work behind-the-scenes, but the Daskals would be the face of the organization, the name printed on all formal communications and publicity materials.

“To her credit, Mrs. Daskal rejected the offer, along with the high salary,” Shaindy relates. “But the fact that the committee wasn’t embarrassed to suggest this speaks volumes.”

Marriage: Not the Be-All and End-All

Where does this superciliousness come from? Why are singles so often patronized or undervalued?

Rebbetzin Tziporah Heller points out that our singles population is enormous, and we haven’t yet learned to deal with the discomfort this engenders. “For most of recent history, you were either a girl, or a married woman. Our generation is grappling with a new reality, and many haven’t managed to recalibrate their perceptions.”

Suri Klein*, a mechaneches who’s been involved in girls’ chinuch for over 20 years, says it goes deeper: the dismissiveness stems from a myopic view of life. “There’s this belief that marriage is the goal. It’s not. There’s only one goal in life: to serve G-d. Marriage and motherhood are one of the most beautiful, profound ways to do that — but there are other paths.”

At the end of the day, Suri stresses, citing the Chovos HaLevavos, it’s going to be you and Him. Snood or not, we all wind up with the same, single, infinitely cosmic relationship: Ein od milvado.

“These facts don’t take away the pain of singlehood; humans are wired to crave a spouse, a family. But when marriage and children become the ultimate goal, then an unmarried person’s life seems devoid of meaning — and that’s a travesty.”

Rabbi Menachem Nissel, popular Jerusalem educator, delineates two kinds of “ideal,” which are commonly confused. On a societal level, marriage is the ideal way to fulfill one’s purpose: Jewish homes form the fabric of our nation, and that’s why much of our chinuch focuses on marriage and children. On an individual level, however, “ideal” means reaching wholeness using the personal deck of cards Hashem deals you. “An older single who serves Hashem is 100 percent ideal,” he clarifies.

The very first mistake Man made, Rav Dessler explains, was to say: “G-d, I have a better idea. If I eat from the etz hadaas and overcome evil from within, my avodah will be more meaningful!” From that moment on, mankind was tasked with a unilateral mission: Serve G-d on His terms.

“Who knows?” Suri says. “Maybe that older single — reduced by some to a one-dimensional, ‘nebach’ character — is actually saving the world! Maybe the woman who gives 110 percent despite unthinkable life challenges, building her character and faith in the most private, authentic ways, is going to bring Mashiach faster than anyone else — because she’s doing the ultimate tikkun for Adam’s cheit.”

Serving Hashem when your life didn’t follow the Bais Yaakov script, Suri acknowledges, is brutally hard. It’s not as personally fulfilling. But after 120, the woman who, despite her overwhelming sadness, says “I’m going to give it all I’ve got,” is the one who will generate an explosion of lights Up There.

This is why singlehood — painful as it is — should never be equated with life-threatening tragedies. “People compare my situation with cancer,” Ahava, a 35-year-old speech therapist, says. “I’m not dying. I wish I was married, but marriage is not life itself.”

Marriage isn’t life — and it also isn’t wisdom. Rebbetzin Zlata Press, principal of Prospect Park Bnos Leah High School, notes that contrary to popular belief — à la Emily Dickinson, who famously wrote “I’m wife; I’ve finished that, That other state,” — entering into a nuptial bond has no automatic transformative effect. “Being married and having kids means… that you’re married with kids. You have not been bequeathed a halo of wisdom, sensitivity, or patience.”

The “nebach” mentality, she asserts, comes from a place of limited horizons: What can she be doing with her days, if she isn’t busy with a husband and kids? “Look around at the extraordinarily capable women who are your sisters-in-law, daughters, therapists, and teachers,” she urges. “Acknowledge the full richness of their contributions. These women will be alive and remembered for generations.”

A Growing Disconnect

Despite these truths, recurring undertones of condescension can lead to a slow but steady disconnect.

Penina, 34, is a successful IT professional who gives weekly shiurim in her apartment. While she identifies with the yeshivah world (“mostly because I want a husband who is a ben Torah, not because I’m enamored of the community”), she understands why some older singles drift away. “There’s this sense that marrieds will never understand us, never appreciate our pain or personal growth. They’ll talk about emunah, for example, as if they’re speaking to tenth graders — as if we don’t know what it means to believe in a loving G-d despite overwhelming, persistent feelings of aloneness.”

Part of the challenge, Penina admits, is that singlehood’s emotional roller coaster is so private. She reveals one tiny but agonizing snippet of her dating career to illustrate: “After dating for ten years, I met a guy I really liked. We went out for months, things got serious. The joy was overwhelming. I had this glow. Then he disclosed that he had a serious genetic disease.

“He sent me his medical records; I spent the next two months consulting with top doctors from across the country, faxing tests, making phone calls, chasing down experts. When I finally gathered all the opinions — it was very, very serious — I had to make my decision. Do I turn down my chance at happiness — or risk a husband who dies within years, or very sick children who die young? Do I hope for the best? He’s such a good person, I really like him! And maybe I’ll never get married!

“Obviously, I consulted with mentors, but ultimately, the decision was mine. The pain was intense. It was like, ‘Hashem, after all I’ve been through, what do You want from me?’

“All this — while being expected to perform well at work, look gorgeous, and keep a huge smile on my face. Because, as we all know, if you show sadness as a single, you must be depressed!”

This episode was just one wild wave in an endless, loopy life monitor — and no one besides Penina’s closest friends knew. “This is the emotional torment singles live through every day. We get the sense that the greater community doesn’t appreciate the depth of the pain — nor how much it deepens us as people.”

The disconnect is exacerbated by the lack of a “yeshivish” support system for singles. As a result, some women — desperate for a safe, empowering place, or simply a place where they can easily meet mature men — seek other pastures.

While many singles create vibrant Shabbos meals and classes, there’s no community-based framework geared to their needs. Some report feeling envious of Modern-Orthodox communities, where singles are embraced, playing key roles in community and shul functions, and feeling a deep sense of belonging. “Some of us are going to be single forever,” Aviva says. “That’s the reality. We need a community for our ruchniyus and our sanity.”

Aviva — who spends her workdays as assistant principal of a school for special-needs children — says she’s contemplated asking rabbanim and philanthropists for help building a kehillah: a rav-presided shul designed for right-wing singles but open to everyone. She hasn’t yet mustered the courage — she worries about being labeled and judged.

She’s already been burned once: when she tried organizing an extended summer getaway for singles, the project’s funders ultimately backed out. They envisioned a publicity-rich initiative that would include press releases and news items; Aviva knew that singles would only be drawn to programming that was discreet and sensitive.

What’s more, the funders worried that an overdose of support would make singles too happy, diminishing their desire to marry. Aviva found that notion laughable. “Are you crazy?” Aviva felt like telling them. “The desire for marriage is inherent, it’s not going away! In the meantime, let’s create optimal emotional health, so we can be better marriage material!

“There’s an organization for everything — sick children, divorcees, widows, orphans, teens at risk — but nothing for older singles. I think singles would be happy to maintain such an organization, if only they felt encouraged and empowered by the greater community. Seed money is a huge issue, but just as critical is the feeling that people really care.”

Singles in Chinuch

One arena in which single women consistently find themselves at a disadvantage is in our chinuch system.

While most unmarried teachers are enormously valued, an unspoken belief lingers: until you have kids of your own, you can’t possibly be the best. At a recent conference, one respected mechaneches voiced this notion before hundreds: “I have a dream,” she announced. “My dream is that a teacher will only be allowed to teach a grade level if she has a child who’s reached that grade.”

Shulamis, a beloved elementary school teacher who sat in the audience, felt punched in the gut. “Parenting experience is a huge asset,” she says, “but it’s just one of a million factors — like emotional intelligence, patience, teaching experience, and energy. There are mothers of ten kids who know less about children than women with one, or none. To pinpoint parenthood as the single most important factor in an educator’s performance is narrow-minded… and silly.”

Rebbetzin Tziporah Heller supports this view. “Sara Schenirer [a childless divorcee] did pretty well,” she notes drily. “Life experience is impactful — but it’s just one factor.”

What’s more, unmarried teachers bring a wealth of unique assets to the classroom: they are energetic, focused, and not sleep deprived. They generally invest hours of preparation each week.

Until recently, however, even outstanding unmarried educators hit a glass ceiling: superbly valued as second-in-command, they were rarely selected to head an institution.

This reality, Rebbetzin Press asserts, comes from a cherished value system: we believe in marriage as the ideal context for growth, and want our girls’ most senior representatives to be women who model that life. “It’s painful, but I understand it,” Rebbetzin Press says.

But Rabbi Dovid Refson, dean of Neve Yerushalayim and numerous international chinuch institutions, disagrees. Parading only role models who fit the perfect image (married, children, husband in chinuch/rabbanus) can generate a dangerous message: you’ll-marry-the-best-boy-in-Lakewood-six-months-after-sem-have-a-perfect-family-and-live-happily-ever-after. A message that can lead to deep disillusionment.

“A role model is made of so many legitimate parts,” he says. “If a single woman is positive, hopeful, and making a life for herself despite a clear interest in marriage, her example can be far more authentic and instructive for thinking girls.”

He notes that the exclusionary model could be used against women who don’t have children, women with at-risk children, or any aberration from the ideal — it’s a dangerous road. “Are there women who become tied up, bitter, or self-absorbed in their pain? Maybe. But that can happen at any juncture in a person’s development, and with any life challenge.”

When a girl is exclusively given role models who are married with children, consistently taught that her mission in life is to marry and have children, and then hits 26… 27… 28, with few marriage prospects in sight, “What do you want her to feel about Hashem?” mechaneches Suri Klein asks rhetorically. “If you’ve just convinced her that Hashem has stripped her of her entire purpose in life, how is she supposed to feel?”

Glorification and overemphasis of marriage as an end unto itself results in girls feeling abandoned by G-d and the community, she says. According to her, it’s not just the unmarried girls who suffer: she fields painful calls from married women who feel betrayed and misled. “These are girls who jumped and married the first guy they met, because they were hyper-focused on getting married instead of who they married. Ten years later, they’re miserable and angry at G-d.”

The solution, Rebbetzin Heller says, is to create a chinuch system that puts self-development and G-dly connection first. “When dveikus b’Hashem is the foundation, external circumstances become much less important.”

Having said that, she notes that the Torah’s ideal path for achieving closeness with G-d is through marriage and parenthood — since they increase our capacity for connection — so girls should be significantly readied for those roles.

Chinuch must prepare a woman to be a self-determining religious being, asserts Rebbetzin Press. Apart from that, there isn’t much we can — or should — do to prepare girls for singlehood. “You can’t get the stars out of a 16-year-old’s eyes, even if you thought it worthwhile,” she says, chuckling. “A fairytale ending is going to happen for her.”

Once a girl hits seminary or beyond, she might be more open to loading up with spiritual and emotional preparation. Alana Rothstein was recently asked by her friend — eim bayit of a well-known Israel seminary — to speak to the students about fulfilling their mission in life, irrespective of marriage. “The girls were really receptive,” Alana reports. “Many had older single siblings. They were eager to acquire tools.”

Girls asked questions like “What do you do with your time?” “How do you stay so upbeat?” “How do you stay connected?”

Alana stressed that every woman develops her own tools for life, but one common thread is: I want to serve Hashem. What can I do today to further that goal?

She shared with the girls a famous story about the Brisker Rav, in which a bochur asked if he could go home early for Pesach: he wanted enough time to go on two or three dates before Yom Tov, so he could be engaged by Rosh Chodesh Iyar. The Rav, renowned for his sharp wit, retorted: “Leave already today, because you don’t want a Shabbos bris!”

“We need to stop keeping cheshbon for every detail of our lives,” Alana told the girls. “Life has ups and downs and curveballs. The only thing that remains constant is our faith.”

Internal Reservoirs of Faith

Their faith is deep, but the day-to-day grind is tough. Practically, single women draw on a rich treasury of truths to cultivate an authentic sense of purpose — and keep going.

“It’s hard to live in a society that considers single life as living in limbo,” says Alana Rothstein. “I tell myself: life isn’t about waiting for what’s to come; it’s about building with what you have. I have a framework in which to serve Hashem. I have my job, my social life, I do chesed. While I hope to get married one day and use that as a medium for avodas Hashem, I’m not waiting around for purpose to come to me — I’m pursuing it!”

Shulamis, who’s dated for 13 years, points out that acceptance of a situation doesn’t mean you’re thrilled with it. It means you have the inner peace of knowing you’re precisely where G-d wants. “Today, I feel very deeply that I’m exactly where I’m supposed to be,” she says, noting that continuous mussar study has helped her enormously. “I’m happy I’ve been able to develop over the years to honestly be able to say this.”

Ahava, 35 years old, says that while marriage is a basic human need — and the pain is acute — “life is too precious” to allow singlehood to consume her. “We all want to make it to the Promised Land — ideally in a minivan,” she explains. “But guess what? Hashem decides which vehicle I drive. I might just have to show up on a motorcycle. I’ll keep davening and working to upgrade. But for now, this is what I’ve got, and I’m not sitting on the curb. I’m pushing forward, I’m moving. With His help, I’m going to make it to the Promised Land.”

In the Footsteps of our Matriarchs

Rebbetzin Tziporah Heller notes that there are two categories of female heroines in Tanach:

• The nashim ba’ohel — women like Sarah, Rivkah, Rachel, and Leah, who are praised for the effect they had on their husbands and families but about whom we know very little as people.
• Women like Rus, Naomi, Yael, and Devorah, who are not represented as wives and mothers; their greatness lay in responding to uniquely challenging life circumstances and events in terms of how can use my gifts to serve Him now?

The Imahos-type woman is primarily represented in Tanach, because through her children, her impact is felt for generations. At the same time, Chazal describe Yael as “gadol mi’nashim she’ba’ohel,” greater than the former, because of the enormous difficulty in stepping up to the plate to do G-d’s will.

“It’s wonderful if a woman can be both — a powerful family matriarch, and a Yael-type heroine who uses her unique strengths for the greater klal,” Rebbetzin Heller says. “But Hashem’s hashgachah writes the script that determines which model is most relevant to which woman.”

In Torah sources, however, femininity — praised as a powerful force — is often represented via mother- or wife-related imagery. Is there a place for femininity in singlehood?

Absolutely, says Mrs. Miriam Kosman, author of Circle, Arrow, Spiral: Exploring Gender in Judaism. Femininity, symbolized by the circle — versus masculinity, which is symbolized by the hyper-achieving arrow — is the power of connection and internality. It’s the force that puts the focus on the process rather than the result, on internal growth and relationship rather than status and hierarchy.

The declaration, It’s not good for man to be alone, is not just about males; it’s a statement about humanity, she asserts. Women, as hawkers of internality, are divine secret agents, pulling mankind to the ultimate truth: relationship with G-d. Without them, society would lose sight of the bigger picture.

“A single woman — like a married woman — can bring the gift of femininity to whatever she does,” says Kosman. “She can be an ambassador of ‘circleness,’ pnimiyus, in any setting.”

A hint to this can be found in the famous explanation of the Akeidas Yitzchak on the exchange between Yaakov Avinu and Rachel Imeinu. “Give me sons or I will die!” our anguished matriarch tells her husband. Surprisingly, Yaakov rejoins with a seemingly harsh reply: “Am I G-d who chose to make you infertile?”

There are two aspects to being a woman, the Akeidas Yitzchak explains. Ishah describes a woman as someone who can understand and engage intellectually — not very different from ish. Chava, by contrast, refers to her role as carrier of life. If a woman can’t have children, then she remains an ishah — and just like an ish, her offspring are her good deeds (Yeshayahu 56: 3-5).

When Rachel said, “Give me sons or I will die!” Yaakov felt the need to correct her misunderstanding: no, you will not be “dead” in relation to our joint purpose, just as I would not be “dead” had I not bore children. We are ish and ishah, and our purpose goes beyond children.

Further, the Maharal notes that pain creates a yearning — an open space, a hole — that works like a vacuum, drawing salvation to the emptiness. Perhaps this is why, Mrs. Kosman suggests, it’s specifically the women who were in painful places — like the orphan Esther, Bnos Tzelafchad or Sara Schenirer — who were able to bring something new to Klal Yisrael.

Fascinatingly, the term eim b’Yisrael has its roots in a context entirely unrelated to childbearing: it’s used to encapsulate Devorah the prophetess in her role as leader. (Notably, Devorah’s children are not mentioned in Tanach or Chazal; it’s not clear she had children of her own.) Just as Devorah was the quintessential eim b’Yisrael, single women, too, can be profound nurturers of this world.

Adopt a Friend… or Two

Looking back at a decade-plus of living alone in Flatbush, Rachel Avigdor Burnham says there were many bright lights — and the brightest, perhaps, were her adopted “parents,” Moishe and Chaykie Rosenthal.

Rachel, whose parents live in New Haven, Connecticut, immediately took a liking to this warm, community-minded couple. The Rosenthals began inviting her for Shabbos meals, and Rachel frequently accepted. “Every woman deals with Shabbos differently,” Rachel explains. “I made plenty of singles’ meals, but to me, Shabbos still meant a family table.”

The relationship grew, and Rachel began bringing along her friends… and their friends. Since that start, the Rosenthals have hosted single women nearly every Shabbos for the last 15 years. “We’ve met wonderful, wonderful women,” Chaykie shares. “We’ve made some very close friends.”

Many singles living in Brooklyn do not have family locally; they’ve moved there for professional, social, or dating reasons (though “the streets of Brooklyn are not paved with men,” Rachel cautions, only half-joking). A loving surrogate family can be life-changing.

The Rosenthals have hosted sheva brachos and facilitated many informal dates in their home (when women wanted them to meet the guy and hear their opinion). They’ve even walked one woman down to her chuppah. They also host an annual Purim and Chanukah party.

“To come home to your basement apartment and light the candles yourself can be very depressing,” Chaykie explains, shrugging off the praise. “If my daughter was living in Chicago, I’d be so grateful knowing that a family offered warmth and support.”

Chaykie shares some tried-and-true tips for creating enjoyable, engaging meals:

• Keep it small and focused. If the crowd gets too big, you won’t be able to maintain a unified table discussion. Plan ahead, and prepare a list of interesting Torah-related discussions. (“This is stating the obvious,” Chaykie says, “but it would be completely inappropriate to ask a guest about her shidduchim. If she solicits your dating advice, be a good listener. Otherwise, it’s not your business.”)
• Stick to one age group. They are all seeking Mr. Right, but that’s where the similarity ends. A 33-year-old woman is not 19 plus 14 years; her vast life experience has led to profound personal and professional growth. To ensure optimal comfort for guests, invite women of similar ages.
• Never on the spot. Extending invitations early on in the week conveys thoughtfulness and genuine friendship.
• Consider inviting men. If you have a knack for facilitating conversation and connection, consider arranging a carefully planned meal with a small number of men and women. This provides singles a kosher way to meet, without the emotional stress of a formal date. And even if the individuals are not compatible, networking can lead to other opportunities.