“In the dark, all cats are gray,” said the rebbe of my ultra-Orthodox yeshiva. I had just confided in him that I proposed the night before to an 18-year-old woman, even though I was not attracted to her—or women in general. I’d had a secret affair with a fellow yeshiva student throughout high school, and I felt guilty and ashamed. I was 23, an age that many of my yeshiva friends were fulfilling their Torah obligation to get married, and I felt the pressure. The rebbe’s “gray cats” advice, an allegory for imagining anything necessary to feel aroused and fulfill your conjugal duties, was a relief. It reinforced my belief that I could reimagine my masculinity, which had led me to Orthodox Judaism during a painful adolescence.That was 1981. These many years later, having just celebrated our 30th anniversary, my husband, Rob, still cannot conceive that I was ever that person with the beard, payos, and black hat, willing to accept someone else’s version of myself. He sees me as a secular, retired corporate HR guy, not a religious radical who left home seeking refuge.I see myself as a reconciliation of opposites.In the waning years of a carefree childhood, something happened. It began when friends, teachers, and parents stopped smiling. A certain kind of indulgence was over, an end to spontaneity. It’s like you are still dancing after somebody turns off the music. That’s when I became aware of an unwritten code. Those who follow it intuitively become its enforcer. You are either a boy or a girl. If you are boy, you are expected to act like one. Be competitive. Be aggressive. Be dominant. The code’s simplicity belies what’s at stake: If you can pull it off, the world is yours. But if you are a boy who acts like a girl, then you are fractured, and not a whole person. And no one wants a broken thing.I was failing society’s expectations of masculinity, as evidenced by my mother’s hounding that I be more aggressive and good at sports, the derision at school of my soft-spoken manner, and my preference for reading and art. Did I miss a memo that the other boys received of how to act? Was I lacking a gene of natural athleticism, or competitive drive? I dreaded raising my hand in class because a group of jocks would mimic my words. I felt the anxiety of some impending consequence I would have to face but I had no name for it. It was a mystery until the answer was revealed on two 1970s TV shows that foretold my destiny: Medical Center and Marcus Welby, M.D., using similar storylines, portrayed homosexuals as a source of shame to those around them. I was convinced my secret attraction to other boys was a mental illness and it was only a matter of time before I would be taken away to a hospital and given shock treatments. I was terrified. I fell into a deep depression.But all that changed the day my father took me to see Cecil B. DeMille’s The Ten Commandments, with Charlton Heston playing the role of Moses. As I sat wide-eyed throughout the 3-hour and 40-minute spectacle, I felt that God was sending me a message: The Egyptians were the bullies of the Jewish people, who were weak and ineffectual. The Hebrews invoked God’s help and were restored to their rightful glory with signs and wonders, as the bullies drowned in the sea. I, too, pined for salvation.In the early 1970s, many young Jews were rediscovering their ancient God through Chabad Lubavitch, the outreach organization whose mission was to gather Jews back to the fold. A Lubavitch neighbor introduced me to several Orthodox yeshiva families in Brooklyn. I was drawn to their rituals and gentle ways, their talk of mysticism and how our persecution through the ages was a noble thing to hasten the coming of the Messiah. A Hasidic family engulfed me with kindness, the warmth of their Shabbos tables festooned with braided egg challahs, fresh ground gefilte fish, and glazed chicken. A white-bearded rabbi, wearing a sable fur streimel and silk caftan, placed me next to him at his table and became my mentor. I was ready to put my faith in bearded holy men because they provided a model of maleness that was achievable for me. I, too, could grow long payos and a beard, wear a black yeshiva hat, and tefillin. These trappings were uniquely male, yet they existed in the spiritual realm, not the aggressive, competitive masculinity of secular society that rejected me.And so, at age 15 in 1974, I announced to my parents that I’d be attending an all-male yeshiva high school 400 miles away with a full scholarship. I grew a beard and long side curls, observed the Sabbath, ate strictly kosher food, and withdrew into the cloistered environment of the Orthodox community. I insisted on being called by my Jewish name, Leibel, which means “lion.” I scorned the secular, suburban Jews who I grew up with as nonbelievers, assimilationists, and traitors to their own religion. I was ashamed of my nonreligious Jewish parents, who ate pork spare ribs at the August Moon restaurant, and my father’s profession as a hair stylist. My mother was outraged at my announcement and told me she no longer recognized her own son, that my radicalism was a phase. I yelled at her that we were the chosen people, descendants of King Solomon, that I would no longer be a pushover who was called “faggot,” and got beaten up at Little League practice. I felt powerful in my proclamations. And powerful was something I’d rarely felt.When I left home for yeshiva, I felt that this was my opportunity to recreate myself, reinvent my history, and start at zero. Orthodoxy provided me with a surge of empowerment, with its rules and hierarchies that determined who was in and who was out.Yeshiva high school was an exciting whirlwind of learning Talmud, chumash, and Jewish history, the intricacies of kashrus, and Shabbos. I was accepted into the male fraternity of yeshiva life. It felt like I had acquired hundreds of long-lost brothers whom I could emulate. As young men, we were expected to undertake the yoke of Jewish law by learning, by praying, and growing up under the mentorship of our rebbes. During study sessions, the singsong boom of deep male voices echoed throughout the large beis medrash. There were laws and customs to learn for every aspect of life, a sure way to secure the love of God and the Jewish community. Although many students played a sport like basketball, there was a place for us nerds, the delicate, the academics, and those who aspired to be older, wiser rabbis. Yeshiva maleness didn’t place a lot of importance on mannerisms. We were all in the humble position of proving ourselves to God. I finally belonged.But my world turned upside down when I was overwhelmed by my attraction to another yeshiva student. This became my first love affair, my first passionate kiss, the first time I was infatuated with someone emotionally and physically. It was exhilarating, confusing, but even more, terrifying. The more I learned Jewish law, I realized that I was committing one of the most heinous of sexual sins. Although I would not be of marriageable age for several years, I did not understand how I could fulfill the obligation to marry and raise a family. After two years of this torment, the week before Yom Kippur, I partially confided in my yeshiva rebbe that I liked men, and was afraid of being kicked out of yeshiva if anyone ever found out. His advice was comforting: Don’t act on your desires, live a life of Torah and mitzvahs, all else will follow.I put my faith in my rebbe and resolved to erase my attraction to men through study and prayer.Soon after I turned 21, my father collapsed on the kitchen floor from a massive heart attack. His beauty salon had burned down two years prior and he died unemployed and depressed. This only reinforced my view that I left a secular society where tragedy was born of weakness. I chose strength. The yeshiva community provided solace and guidance. They said it was time for me to get married and join the kollel, the advanced learning cohort of married men.I was introduced to a shadchan, a matchmaker, to find a bride.The shadchan was a stocky, middle-aged woman who wore a snoodlike bonnet, punctuated with a faux jewel at the confluence of folds in the front. I knew even then that her look was a caricature, because shadchans can look like everyone else; they are often family, friends, and rabbis. But her exotic presence suited my need to believe in a guru for magical intervention. We sat at her dining room table as she thumbed through an overstuffed black spiral notebook, crammed with notations. I guessed that this was where the girls were kept.She asked me about myself. What is your background? Which yeshiva do you attend? How long do you intend to stay in learning after marriage?She asked if looks were important to me.I told her that marrying into an Orthodox family was important to me. I wanted to be able to go with my wife to her family on Shabbos and Yom Tov, to sit at their table and drink their wine at kiddush, to call my in-laws “Tatty” and “Mamme.”Over the next two years I was set up with 12 girls, some by the shadchan, others by yeshiva friends and the occasional rabbi. The dates always seemed flat and awkward and rarely went beyond the first time. But then a fellow yeshiva student and friend set me up with his sister, whom I’ll call Shayna. She was an enviable catch: the daughter of an esteemed rabbi in New York City. Others remarked on her charm. They said she looked like Lady Diana. I wanted to feel what my friends saw in Shayna. I wanted to love her, to appreciate her beauty. But I was not in love with Shayna, nor did I feel any attraction to her.Yet I proposed and she accepted.There is nothing more exciting and dramatic in the ultra-Orthodox community than a young man reaching the milestone of engagement and marriage. I was proud of the idea of joining the ranks of Jewish married men who wear a tallis during prayer, of walking with their wives and children to shul. I craved the excitement I would soon generate with my announcement; the loud mazel tovs and slaps on the back from my friends and rebbes. Thoughts of a chasuna, an Orthodox Jewish wedding, the poignant ceremony where I would be escorted by candle bearers under the chuppah, the raucous dancing and music, all of it, all of it would be a vindication, a shedding of my frail skin of uncertain masculinity.The next morning, however, the terror of what I had done had me in tears as I told the head rebbe of my yeshiva everything: my liking men, my lack of desire for women, and my motivations for wanting to marry Shayna. His advice was gentle but pragmatic: Call off the engagement and look for a girl based on personality and friendship. It was comforting to learn that I was not the first to ask his counsel about this, and that others having same-sex attraction were still able to get married and raise families. I can still hear his voice in my head. In the dark all cats are gray. He ended with: “Your wife will never have to know.”My belief in Orthodox caretakers and the refuge they provided persisted, even after leaving yeshiva and living independently in the Orthodox neighborhood of Boro Park, Brooklyn. I became a computer programmer and joined an Orthodox, family-owned company that was paternal and kind to its employees. I started seeing a bearded, Orthodox psychologist who specialized in behavior modification. He was a member of the psychology department at a city hospital and ran a practice out of the basement of his home to treat Orthodox clients. He explained to me that through cognitive therapy and hypnosis, we could discover the trauma that led to my abnormal desire for men. He explained that some practitioners resort to aversion therapy such as electric shocks or nausea-inducing drugs when shown sexually arousing images of men, but he preferred that I simply snap a rubber band around my wrist whenever I was tempted. To increase my arousal for women, he explained that some rabbis have permitted a man to use a prostitute to practice.For the next few years, I continued to go out on shidduch dates and see my psychologist every week. We never did find the elusive source of my sexual preferences.I had now been introduced to a total of 28 women.The turning points in one’s life do not always happen as dramatically as in the movies. I was in a small rowboat in Clove Lake Park, Staten Island, on my 29th and last shidduch date. I was 26. I sat across from her young self. I thought how this romantic setting would be ideal for people in love. But I was an impostor. I knew how I could mess up her life as well as my own by living a lie. The holy men could tell me how to live my life, but they wouldn’t be there for me in a loveless marriage. While the divorce rate is low in the Orthodox community, I had witnessed several of those marriages unravel, and how rabbis blamed it on unrealistic romantic notions proffered by secular movies and books. But I was born of movies, and my imagination was ignited by books.At that moment, I began living a dual life.On Friday nights I would sneak out of Boro Park, dressed in a baggy suit and hat as if going to shul, but underneath lay jeans and a polo shirt. I’d walk a mile out of the Jewish neighborhood to my car that I left in a Pathmark parking lot. I would peel off the layers of yeshiva clothes and drive to the LGBT Center in the West Village. I was awkward in these new circles, but I made friends. I was invited to Fire Island weekends and loft parties in SoHo, attended ACT UP meetings, and met others who were coming out and recovering from shame. I had my feet in both worlds, while keeping them separate and hidden from each other.On one of these sneak-out evenings, I met Rob, my future husband, at the gay synagogue, Congregation Beit Simchat Torah. We moved in together only six weeks after we met, and found an apartment away from the Orthodox neighborhood where I could finally breathe and build a life.For the next six years, I hid my relationship from the close-knit Orthodox company that I worked for. I was still holding on to the safety of a world I had chosen years ago. My father’s death haunted me, and I was petrified of taking on the complexities of a new, secular work environment and to fail as he had.One day I came out to a very religious coworker, whom I’ll call Yakov, to stop him from pestering me about going on shidduch dates. He was outraged and told the other employees. That began six months of misery. One by one, people who I worked with for years began to avoid me. Yakov bullied those who were ambivalent into taking a strong position against me. When I entered rooms, conversations stopped. One coworker told me that AIDS was God’s plan to cleanse the world of feigalach, prostitutes, and drug users. One morning, I found an extremist Orthodox newspaper on my office chair open to an article that declared homosexuals deserving of the death penalty. In a group photo that hung in the lunchroom, my eyes were poked out with what appeared to be a thumbtack.Scorn and bullying were the very things I fled during adolescence. I had not expected it to come from a community that provided refuge to me for so many years. As much as I felt betrayed, I knew that it was not them who changed. Their rules remained constant. I had changed. They felt I betrayed them, that I lied, by taking up residence among them, allowing them to think I was a good Torah Jew. And now the terms of the compact became clear; kindness and inclusion were only given to those who followed the laws of the Torah, knowing your place, and assuming your role as a man.Rob urged me to quit and walk away clean; not to sue them, not to throw more energy at a situation that had deteriorated years ago. I knew he was right. I had abdicated my powers of discernment to rabbis, matchmakers, and psychologists, who mercifully, at my request, offered ill-fitting clothes. I quit my job, and leaped into an uncertain future.I was now able to resume a life deferred. And to ask the tough questions: Who am I really? What is the thread that ran throughout my extreme choices? What do I want to become? It soon became clear. It was not the pursuit of maleness that had propelled me. It was the idea of transformation. I became fascinated by the mechanisms of empowerment and influence, which led to a new career in leadership development in corporate America. I went back to school. I learned the art of executive presence and became a confident public speaker. I coached nervous managers to overcome their fears during corporate downturns. As a boy, I craved an instruction manual of how to be a man. As an adult, I harnessed my penchant for clarity by providing others with a road map for effective leadership. I feel empowered by helping others transform.My religious observance fell away gradually. The more I established myself in the secular world, the less meaning I felt from religious rituals and obligations. This presents an ongoing challenge. Rob and I have deep connections with Judaism but from opposite ends. He lived and worked on a kibbutz, and was raised in a close-knit Reform Jewish community in the suburbs. When he insists that we attend services in a non-Orthodox synagogue, I can’t help but feel I’m drinking skim milk—a watered down version of a richer, truer, practice. I remain nostalgic for the vibrant pageantry of ultra-Orthodoxy. Yet my attachment to Judaism remains strong because of my focus on transformation. It draws me to Jewish mysticism and its enigmatic path to enlightenment. According to the Zohar, life is built on opposites that we must resolve to achieve tikkun olam; male and female, failure and success, weakness and strength. My life is a reconciliation of those opposites by learning to live with contradictions. I’ve finally become whole.