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“If I could work magic in your dating life,” Israel Irenstein says, “what would you have me change?” We’re sitting at a table at Pret A Manger in Union Square, and Irenstein, a 35-year-old dating coach dressed neatly in a pale green Tommy Hilfiger button-down, is talking with Sam, a 29-year-old ex-Orthodox Jew. Sam looks terrified behind his wire-rimmed glasses. Clutching the strap of his bag under the table as if it’s the leash of an unruly dog, he displays an impressive commitment to deflection—responding to Irenstein’s personal questions by spouting perplexing theories, including, “A major aspect of the notion of getting better at dating is not about increasing the total numbers, but increasing the yield of the process.”

Irenstein tries a new angle: “Who do you think wants sex more,” he asks Sam, “men or women?” Sam concedes that this may not be a universal truth, but in his experience women totally want it more.

According to Irenstein, lack of self-confidence pervades the recently ex-Orthodox, who refer to themselves as OTD, or “Off the Derech” (derech is Hebrew for path). Once they’ve gone off the path, for a variety of reasons including loss of faith, distaste for the lifestyle, and longing to educate themselves beyond the Jewish texts, OTD’ers are like immigrants in the secular world, unsure of the language and customs of dating, battling the voices of their parents and rabbis, who warned them that touching the opposite sex before marriage would incur God’s wrath.

“There are three problems specific to the ex-religious when they first try to date,” Irenstein says. “Inexperience, having no identity, and having no understanding of the opposite sex.” That makes sense when you consider how insular the Orthodox communities are. Premarital sex, even premarital touching, is prohibited. And there is a rule for everything, including which shoelace to tie first and what to do with one’s facial hair. OTD’ers who come to Irenstein never had the awkward, albeit formative, experiences the rest of us had—slow-dancing with some height-inappropriate partner in seventh grade, locking braces with someone in the back of a movie theater, getting to “second base.” Their questions for Irenstein range from the peculiar such as, “Is it OK to pay a girl $80 to go out with me?” to the commonplace concerns of men on the New York dating scene: “How many dates before I should allow her to split the check?”

Irenstein doesn’t just answer their questions about the game; he shoves the men out onto the field. By the end of his session with Sam, he’ll have Sam approaching girls, trying to score a phone number, or at least to touch an elbow during some flirtatious banter.

At 29, Irenstein was married with two daughters, living in the Hasidic community he’d grown up in. He remembers his 6-year-old coming home from school and telling him that non-Jews existed solely to witness the good deeds of the Jews. He’d wanted out of Hasidism for a while, but that was the day he pulled his kids out of school and laid plans to move. “I would have done anything,” says Irenstein, “even given up my own life, to make sure my kids weren’t forced into cult living.”
 

Having grown up in Israel and Brooklyn, Irenstein landed in secular New York with a third-grade-level education and a mediocre grasp of English. When he and his wife divorced, he found himself on foreign ground. “I had no idea how to talk to women,” he says. “I’d never even looked one in the eye.” Irenstein’s former Hasidic community, Gur, is one of the strictest sects, as well as one of the most sexually squeamish. Even married couples aren’t supposed to kiss, and they’re allowed sex only for purposes of procreation.

Frustrated by his own cluelessness, Irenstein turned to pick-up artists and dating coaches, including New York Dating Coach, as well as to self-help books, Tony Robbins’ confidence-building seminars, and therapy. He was less interested in learning pickup lines and routines than he was in retraining his brain; he wanted to project self-confidence. Today, that’s what he teaches—that if you feel good about yourself, you’ll have an easier time with the opposite sex. It sounds basic, but to many OTD’ers, it’s not.

A naturally outgoing person, Irenstein learned quickly and his dating life began to thrive. He, became a dating coach himself, sometimes freelancing for New York Dating Coach, other times taking on private clients. But he doesn’t charge for the one-on-one coaching he offers people like Sam and the dating seminars he conducts at Footsteps, a nonprofit that helps OTD’ers assimilate. “People helped me,” Irenstein says, “so I make it a point to help others.”

http://www.slate.com/articles/double_x/doublex/2012/04/dating_in_new_york_a_dating_coach_for_ex_orthodox_men_.html