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I came to Jerusalem with the intention of being a true pilgrim, making some kind of honest and open tshuva (return to Jewish law and observance) – in my fashion.

What clinched it was my sister’s announcement in September ’04 of her engagement to be married at the end of October. I would be coming to Jerusalem, at least for her wedding, and take it from there. I began to allow my beard to grow, in anticipation that it would come in handy. Both as a beard and a ‘beard.’ I knew somewhere in the Torah, the Talmud, somewhere Jewish law or custom said you should have a beard. Certainly a man of my age -- while I was (and am) frequently flattered to hear that I look a virile early 30s, I was, in fact, on the verge of 40 at the time of my trip. But the beard would cover more than my chin; I thought it would help me pass in a community that, if they knew everything about me, might never let me in.

Really, my desire to come and learn in Israel dates from my teens, when I spent a mediocre and frustrating few years in Hebrew School at my suburban New Jersey Conservadox synagogue. While I had been a curious, adept student, the quality of the teaching and programs varied so widely, and worse, the commitment of the other students and their families was so conflicted, that the atmosphere inhibited genuine learning and growth as much as facilitated it. And while we were only 45 minutes drive from New York City, probably the largest and most varied Jewish population in the world, we rarely made use of that vast resource, and instead were cooped up with our teachers in our cramped cinderblock classrooms, filled with adolescent hormones, frustration, and confusion about just why we were here For those few of us with a genuine interest in learning, the experience was even more hellish because the student disdain and acting out made it impossible to focus. Judaism was tantalizingly close, yet ultimately remote.

No one could explain to me what the big deal was, really, about being Jewish -- and if it was such an ancient, true, noble thing, then why Hebrew school was such a joke, and the services were, at best, melodromatic, campy mumbo jumbo, which few really seemed to understand or appreciate. There were a few older men in the congregation who clearly knew what was going on, because they had had genuine, effective Jewish educations when they were younger, clearly somewhere else (typically, Europe before the war). But otherwise, no one seemed to care. Very few people kept Kosher at home. Few kept Shabbat. I’m not sure I would have survived synagogue with any positive Jewish identification at all were it not for the choir.

Blood and Iron Steele, Der Eiserne Kantor, I dubbed him. Trained in the top cantorial school in Berlin before WWII, Joshua Steele had come over as a young man, together with the congregation (which was led out of Nazi Germany in 1938, the last year such an escape was possible, and somehow ended up in suburban New Jersey). He led the choir with an aging, yet still iron, classically Prussian fist, and an increasingly threadbare but formerly glorious heldentenor voice. I had started singing in the choir as preparation for my Bar Mitzvah, but I quickly became hooked. The services were still fairly classical Yekke services – composed by Lewandowski, a mid 19th century Jewish composer, who wove traditional niggunim into a larger oratorio structure, so that much of the service was one, long musical offering (8:30 am to 12:30 pm on Shabbat mornings). The choir was critical to this structure, and is to this day the most memorable part of my Jewish upbringing.. I could probably reproduce much of those Kabbalat Shabbat, Shacharit, and Musaf Shabbat services from memory, and even today when davening them, it’s that service, that choir, and the voice of Joshua Steele still echoing in my mind.

Aside from the choir, though, there was nothing to keep me engaged in Jewish education throughout my confused, closeted teenage years. Later in high school, then at college, I would return to sing in the synagogue choir for the holidays, and to lead my family’s Passover seder each year. I was the most educated, interested and religiously adept in my family, but I still craved a passionate, committed world of Jews living and learning and seeking to integrate Judaism into their modern, worldly lives.

I came out when I went to college, but, while I had various and occasional boyfriends, they were far fewer and further between than I’d ever envisioned, with long periods of loneliness. I’d never found love. And finding a nice Jewish boyfriend with whom I could also be passionately interested, and turned on, and sexually compatible was beginning to feel like waiting for Moshiach. The two Jewish guys I’d dated were painfully unsatisfying in very different ways. Rob was a handsome, tall, lean, long distance runner from Chicago; very smart, very diligent. I’d spied him several times at Columbia’s gay dances, and wondered out loud to a friend who lived in his dorm how I might meet him. Somehow, meet him I did, and while I was fumbling through small talk,I invited him home to my family for Pesach. At that time I was in the process of emotional, educational meltdown – I was behind in all my classes, behind with papers, and was missing classes to try to catch up with what I could -- and was generally in a state of neurotic denial. Nonetheless, the hottest Jewish gay boy I knew on campus, brilliant, athletic, romantic at times, had accepted my invitation home for the Passover. Perhaps surprisingly, things went very well. We very discreetly played a little footsy under the table, as I again led the seder for my clueless family, and we made out after hours upstairs in my room. This led to a three week period where we met almost every day for at least an hour, usually in a park just off campus, to have lunch, schmooze, and make out just a bit. It was deliciously like the classic romance I’d never had. Yet while I had managed to mostly keep the reality of my educational and emotional implosion hidden from him, he was beginning to get an inkling. When finally he’d finished all his exams, and the fullness of my disaster played out, the sex we had was passionate if neurotic. Our final day together came with the revelation of the fullness of my last semester’s crisis, and him telling me just how fucked up that was and how I needed help, and he needed to move on.

My only other Jewish boyfriend, David, was a small town political operative in New Jersey, on the town council, involved in Democratic politics, with a patronage job working in the office of a local politician. Totally closeted, with a budding ulcer, and with deep hangups about his body and sex. Not the brightest bulb intellectually, socially, or culturally either, and within three or four months of commuting to suburbia for this, I bailed.

All my other boyfriends were goyyim, who, while exciting, titillating, emotionally engaging, lacked one little thing: being Jewish. Mario, my little bed monkey and renaissance English lit scholar. Gregy, the pretty blond twinky actuarial student, whose career was a metaphor for his pathologically cautious and repressed emotional life. Mark, the totally hot and dramatically self destructive masochist with whom I’d had the best sex of my life, until his ongoing spiral of self destruction led him to a boyfriend who really abused him. Roberto, he of the platano grande, the macho latin lover who taught me – Ai! que rico, que suave, que sabroso! -- how to love sex. Dionne, the buff, hung, young black stud whom I met on the internet, with the wild sexaholic background and amazing feats of fetishistic derring do... Those and others, all exciting, appealing, amazing, romantic, hopeful -- and all not Jewish. While I felt I might have loved any of them, I wanted marriage... permanence.. yiddishkeit. Where were the hot, nice, available Jewish boys?

Careerwise, I had ridden the Internet craze at a top Wall Street investment bank all the way to the Firm Management E-Commerce Strategy Group, just to have it all evaporate beneath me. I was laid off a week before 9/11/01, and, with meaning I’m still fathoming, missed my meeting on the 41st floor of the World Trade Center II at 9am that morning by oversleeping. I spiraled through a series of dismal, short term jobs, financial disaster, and the eventual loss of my Park Avenue South apartment, into a guest apartment attached to my parents’ home in Jersey.

So it was time for a change; a leap out of the unfulfilling mess of a life in which I had fallen, and a leap into new realities. I wanted to explore what had so inspired my sister to transform her life from modern, independent, rising fashion industry exec, to marrying a yeshiva bucher met through a shadchan (matchmaker) after only five weeks of dating, and to the very traditional role of wife and mother in Jerusalems’s haredi (ultra-orthodox) community. It was time to explore more fully what this Jewish thing was all about, how it worked, where it came from, and what it might mean for me. Even me: the campus gay leader, founder of an Ivy League AIDS education and activist group, past president of my university’s LGBT group, co-founder of the international gay foot fetish organization -- the very model of the modern homosexual. If I could survive and thrive in one of Wall Street’s tightest, rightest, whitest, old-school investment banks, I thought, I’d survive haredi Jerusalem.

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