Abby Stein: A Gender Transition Through a Jewish Lens

Transgender woman Abby Stein—or, as she prefers to be dubbed, “a woman of trans experience”—is in a bit of a quandary. The 26-year-old Columbia University undergraduate, majoring in gender studies and political science, has been approached by a number of major designers, asking her to represent their respective lines. It’s fashion-forward politics on parade, and she looks damn good in the glam/elegant dresses. These are high paying gigs; still, she equivocates.

“I don’t want to commercialize my identity, but on the other hand fashion could be an advocacy statement, a way to reach people,” says Stein, the first openly transgender ex-Hasid and a lightning rod for Hasidic trans-youth in the throes of gender identity anguish. She is an outspoken activist on behalf of the LGBTQ community and an in-demand speaker at universities, synagogues and community centers.

Stein embraces her identity and lives her life out loud, wanting the world to know who she is and where she came from: She was born a boy and named Yisrael, and she is the 10th generation descendent of the Baal Shem Tov, founder of the Chasidic movement. Stein grew up among 13 siblings in Brooklyn as part of an austere and insular sect.

Stein’s first language was Yiddish, and she didn’t speak a word of English (her fourth language following Yiddish, Hebrew and Aramaic) until her 20s. She had an arranged marriage at 18, gave birth to a son and finally jumped ship at 20, beginning her gender transition at 23. Nonetheless she still finds herself straddling a tenuous line between self-celebration on the one hand and self-exploitation on the other; between serving as an inspiration and violating her own sense of privacy.

Several months ago she appeared in a Vogue fashion spread clad in a bra and panties. It was a photo shoot on Hasidic women forging new identities. Stein recounts ambivalent feelings about objectifying herself in that way and her almost daily outpouring of hostile email, including statements from individuals who wish her dead, rose exponentially.

I meet with Stein at a Columbia University eatery where she is preparing to eat a tossed salad and eyeing the options in salad dressings. To indulge in flavorful foods is almost an act of defiance. “You have to understand that where I came from there were no spices used in cooking or eating, none at all,” she says. “When my mother used Paprika once—that was a very big deal.”

Clad in a pretty floral dress with a matching lavender cardigan, Stein could easily “pass”—and that’s her goal, she admits. But true to form—once again underscoring her many contradictions—she also sports a necklace pendent adorned with the transgender symbol, an amalgam of crosses and arrows extending from a circle. Pointing to it proudly, she says, “I’m not trying to hide who I am. I don’t need people to stop and stare at me on the street and wonder.”

Stein always knew she was a girl. Eschewing the clichéd phrase, “a woman trapped in a man’s body,” Stein says, “I’d rather say who I was and the gender listed on my birth certificate did not get along.” It’s a self-consciousness that began very early.

Stein describes an episode that took place when she was four years old, though in retrospect she’s uncertain if it literally transpired as she asserts or represents what someone else told her or the distortions of her own memory—or, in varying degrees, all of the above. But the image of herself sitting in the bathtub with an open safety pin in hand, pricking away at her penis lingers.

“My mother walked in and asked me what I was doing and I said, ‘It feels like it doesn’t belong there,’” she says. “I also remember getting the message that this was something I could never discuss with anyone. I didn’t know anyone else like me until I was in my 20s. It was terrifying.”

Still, she found some comfort as a teenager in a text from the Kabbalah that says a man may be reincarnated into the body of a woman. The Kabbalah’s view of gender is fluid, and that helped, but not enough. In the end Stein simply stopped believing in God, which led to her self-imposed exile in the wake of a Yeshiva education and the completion of a rabbinical degree when she wore a beard, payos and donned the long dark clothes and giant fur-brimmed hat right out of an 18th-century Polish shtetl.

She joined Footsteps, a supportive haven for former ultra-Orthodox Jews who have a difficult time entering secular society and in many cases are totally abandoned by their families and former friends. Stein is well versed in the experience. Her 180-degree turning point occurred when she went camping on Yom Kippur and ate pork. Her first exposure to a film was the gay flick Magic Mike. (Most Hasidim do not attend movies or even own a television).

Looking back, she says leaving her religious community was a far more difficult experience than transitioning, though they share much in common, as each transition calls for total self-reinvention, from how you to dress to how you speak to how you present yourself in the world. “But the difference for me is that when I left the Hasidim, I didn’t know what I was getting into,” Stein says. “By the time I transitioned three years later, I had done a great deal of research. I knew what was going to happen and how it was going to work. So in that way it was much easier.”

Asked if she’s comfortable describing the details of her transition, she says she’s taken hormones and “done everything,” waving her hand up and down her body, but refuses to elaborate further. It’s nobody’s business, she says, making the further point that you don’t need any medical procedures to transition. If you feel you’re a woman or a man, that’s who you are.

Equally sensitive is her sexuality, though after a few moments of equivocation she says, “I’m somewhere between a bisexual, a lesbian and a demisexual, which means I’m physically attracted to personalities.” She pauses. “It’s not that I’m uncomfortable with these questions; it’s just that the media generally exoticizes us. Would you be asking a person who is not transgender these questions?”

One topic that is unequivocally off-limits is her son and her relationship with him. Her ex-wife, parents and 11 of her siblings do not recognize her in any way. However, one brother and sister (whom she does not want to identify) have maintained a relationship with her.

Yet another transition occurred several years ago. Consider this: Stein now lights Shabbat candles on Friday night and observes the Sabbath to the extent that she does not work or study on Saturday, though she will use a computer. “No, I don’t believe there’s a Boogie Man in the sky who says, ‘Oh, you turned on the lights on Saturday.’ But I like the physical ritual of lighting the candles that tells me the week is over and the weekend is starting.”

“I haven’t gone back to Judaism,” she continues. “I see it as moving forward. Ironically, it started with the food. I was at a friend’s house on a Friday night and they were serving all the traditional foods and I felt, ‘I can’t eat that, it’s too Jewish,’ but I realized how much I liked the food and missed it. And then there’s the Jewish music and holidays. I love them as well. How do I define my Judaism today? I don’t like to define myself. I’ve been in enough boxes. But if I have to define it, I’d say it’s Jewish Renewal.”

When I ask which identity is more self-informing—being Jewish or transgender—she says the latter, because you’re born with an assigned gender. It’s who you are. By contrast, Judaism, or how you practice it, is a choice and as such arguably less defining. That said, she concedes Judaism has informed her transgender experience, and on the flip side, her transgender experience has informed her Judaism.

For starters, she’s become more culturally Jewish than ever before because of the large number of Jews in New York’s Queer community, she says. Columbia University’s Hillel club and even the school’s on-campus Chabad (Chasidic) chapter have been more than welcoming and inclusive; all of it giving her a new, if not renewed, sense of Jewishness.

At the same time she’s able to appreciate her transgender identity through a Jewish lens “by creating a curriculum on gender and Judaism, sexuality and Judaism, Queerness and Judaism based on the writings in primary religious texts, which give trans people legitimacy within the Jewish community,” she says. “Not that I think the texts are necessary for legitimacy, but they do take advocacy to a whole new level. I’ve created more than 30 such source sheets and posted them on the website sefaria.org.” Some of her titles: “From Tolerance to Celebration: How Judaism and Shauvot Teaches Us to Embrace Diversity/LGBTQ and Celebrate It,” “(Trans) Gender in Kabbalah (Jewish Mysticism)” and “Bereshit: The Genesis of (Trans) Gender.”

So what’s in Stein’s future? She’s writing a memoir and toying with the idea of getting a masters degree in public affairs once she completes her undergraduate degree. “Should I win the lottery,” she says, “I might consider staying in academia.”

Stein is most interested in working in the non-profit arena and addressing public policy issues, from gender equality, education, and justice reform—specifically, ending cash bails for defendants charged with petty crimes. “As it now stands, those who have no money can sit in Rikers Island for months waiting for their trial,” she says, “and that’s not fair especially for minorities who are disproportionately incriminated.”

Her days are full and often rewarding. She mentions in passing—though her pleasure is evident—that to kick off Gay Pride month, Brooklyn President Eric Adams just honored a group of LGBTQ activists including New York Times columnist Charles Blow, Council Speaker Corey Johnson and Abby Stein herself.

Simi Horwitz is a multi-award winning arts reporter and film reviewer, whose work is published in The Forward, Film Journal International and American Theatre, among others. She was previously an on-staff feature writer at Backstage.