When Sara Glass consummated her marriage, she was wearing the Victoria Secret’s underwear that her girlfriend picked out.

For Chasidic women, their wedding is like Yom Kippur — a day of atonement — and Glass, 19, had not eaten all day. Every aspect of her life had been planned, from who she would wed to her big white dress. The underwear was a transgression that hid the wedge that would drive her away from her community.

Glass had made love long before her wedding day. She had been dating an older woman covertly for months while both were courting men for marriage. Working with matchmakers and family members, they were each looking for a yeshivah bachelor to settle down with, but before that day, they passed each other love letters and sneaked into each other’s beds. The pair even holidayed together before Glass’s wedding.

Sara Glass on her wedding day. She had only met the man who would become her husband a few times before they got married

“In a world where no one knows what to look for, it is easy to hide,” Glass says over Zoom from her home in Manhattan. “No one questioned two women on holiday together in the lead up to a wedding.”

Glass’s double life as a Strictly Orthodox wife and lesbian lover forms her memoir, Kissing Girls on Shabbat, a cascading tale of being gay in the Chasidic community and breaking free.

Growing up in Yiddish-speaking Brooklyn, Glass didn’t know the word gay or lesbian. “It was the late 90s, so queer representation wasn’t what it is now. I never saw women walking down the street holding hands. I would go to the library and take books out about people who weren’t Jewish, but none of them were queer.”

At 15, she had her first romance with a girl. “I didn’t know what to call it, but I thought it was a sinful thing and I kept trying to repent but couldn’t ever stop doing it.”

By the time she was in a relationship with a woman at 19, she knew it would have to end when her marriage to an unknown man was arranged. “There is a concept in Judaism where you are forgiven for all your sins on your wedding day and so, a week before my marriage, I ended it,” Glass says. She wanted to commit to the married life she had been prepared for her whole life.

Sara Glass, aged 19

Once married, “I thought I was doing everything right, I felt I was on the right path, I was pregnant.”

Barely a month into her marriage, her first pregnancy miscarried. Glass experienced bleeding over Shabbat and — as the newlyweds did not use electricity over the Sabbath — her husband forbade her call for medical help. “It was really hard to know that I was not allowed to make the phone call I needed to get help. How could I follow this rule that led to me losing my child?” This would be the first time that Glass questioned the Orthodoxy of her world.

Glass’s husband had agreed before their engagement that she could complete a PhD in psychology. But soon after their wedding, he had changed his mind. She was to go to social work school and learn skills she could bring back to the community. Nine weeks after having her first child, Glass headed to Rutgers Community College. “It was my first time leaving the community. I was 21 but showed up in a wig, a wedding ring and a long skirt. Everyone else was in cut-off jeans.”

Each morning, she would read Jewish theology texts “to make sure my mind didn’t get too poisoned by social work school”. At home, her husband did not want her new books to “contaminate the holiness of their home”.

At Rutgers, Glass saw a world beyond her own and struggled to comprehend what her desire meant. She recalls one lesson: “A professor showed the class a film about gay rights, I flipped out because here were all the people doing all the things I wanted to do.

Sara Glass

“I stopped and stared; I could not breathe. I left the classroom because I was so worried about being poisoned. If I saw too many things, I feared that I wouldn’t be able to scrub them from my mind.”

At college, she saw that all relationships were different and, not long after having her second child, understood that her marriage was not working. The pair tried therapy, but they barely spoke, and the marriage felt like a “business agreement”. Like the end of all business agreements, divorce requires a contract, and to secure her get, Glass had to agree to raise her children within the strictly Orthodox world.

Signing the document without any outside advice, Glass “agreed that if I stopped raising them religiously, then I would be  ceding custody to their father. Their definition of ‘religious’ was the 613 commandments of Orthodox Judaism, and they added on two other heavy books of commandments.”

This was intense, but not unusual in the community, and meant that Glass had to remain within the Orthodox world with her children.

Unlike many other Chasidic women, however, Glass had a means of income and knew what the world looked like outside her community. When she sent her children to their father for weekends, she would escape her neighbourhood: “I would throw my wig in the back seat of the car, put on jeans and eyeliner, and go to gay bars. I would date men and women, drink and experience nightlife.”

Her children had no idea that their mother, by then in her mid-20s, had two wardrobes and two lives.

She cut out her weekend escapades when she met another man who she would marry. Her second husband was modern Orthodox, which meant they could “blend into regular America a little better than my old community”. He supported Glass with her PhD and helped her set up a private practice as a clinical psychologist, which she still runs today.

It was her sister’s untimely death that, Glass says, “made me realise how finite life is and that I was lying. I wanted to take the mask off.”

Although she had left the gay nightclubs, Glass kept falling for women. “I kept finding myself having feelings for women and our marriage had insecurities because of it. Eventually, he said, ‘I think you’re gay’ and for the first time I didn’t fight it and said, ‘Yeah, I am.’”

Her second divorce soon followed. By then, Glass was confident that her children would not be taken away from her by the clause in the get. “It was strategic because the children were 12 and ten, so they were old enough to testify in court and for their words to matter. It was a safer point for me to deviate from religion than when they were younger.”

Deviating was a gradual process for the family of three, which began with Glass giving her children choices. “Initially it was asking them what they wanted for Shabbat lunch, it didn’t have to be the traditional meal we always had, we could have sandwiches, and then I let my daughter have choices about what she wanted to wear.”

Glass, at last, existed in one world. Now 39, she lives in New York with her three children.

The two from her first marriage, now 18 and 17, have left the strictly Orthodox world and have changed their Yiddish names. Her eldest, Victor, is headed to medical school and they were shopping for a prom suit the day Glass spoke to the JC2. “You could never have imagined we would be able to do this normal American thing together.” It’s a sign of just how far they have come.

Glass has had relationships with women since her second divorce and her youngest son, four, was conceived via IVF and has two mothers, although the women are no longer together. He goes to a Montessori school, which emphasises play and choice. “Let me raise this one right, this one should get to choose from the start,” she says.

Glass’s connection to the community she grew up in is now through her work, “I have a unique skill set. I am a trauma therapist and I speak Yiddish.” But she does not speak to most of her extended family.

Writing the memoir has been cathartic and she is working on book two. Her process has mirrored the stages of grief — an emotion she has been grappling with since leaving the Chasidic community. “My first version of the book was angry. I was in victim mode, blaming all the people and systems who held me away from freedom. But I didn’t want to paint my whole community as bad and myself as the hero. I made a lot of mistakes and there were people in my community who were so warm to me throughout. And so, I rewrote it with more compassion for the people involved.”

Sara Glass with her new memoir, Kissing Girls on Shabbat

She has had requests from women in her old community asking for Kissing Girls on Shabbat to be posted to them in discreet wrapping so that their families will not see it and she recorded an audiobook so that others can listen to it in secret. On social media, Chasidic women secretly follow her with fake usernames.

This, Glass says, is exactly why she wrote the book, “for anyone in the world that is out there with something they feel they must hide.” And for the children from her first marriage, Victor and Jordan, as she says in her acknowledgements, “It has always been for you, all of it.”

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Kissing Girls on Shabbat is published by Atria/One Signal Publishers, an imprint of Simon and Schuster.