“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.”

“At Footsteps, the men come in wondering, ‘If I go with someone to a movie, how do I know if it’s a date or if we’re just friends?’” says Lani Santo, the group’s executive director. “‘Where can I meet people to date? Can I only meet people in bars? That’s what I’ve seen in movies.’ When people are segregated by gender from a young age, learning how to navigate dating and relationships is an enormous challenge.”

Ryan Pollack, a 35-year-old Footsteps member, reminisces about his early days in the secular world. “I met girls,” he says, “but I was constantly in the ‘friend zone.’ I had no clue how to take things to the next level.” When he met Irenstein at Footsteps, Irenstein invited him to a pool party. Pollack brought a girl with him and Irenstein pulled him aside to say, “She likes you. Kiss her.” Never having kissed a girl, he was scared, but with Irenstein’s encouragement, he went for it. “That changed my life,” Pollack says. Soon after, Irenstein took him shopping. Since growing out of baby clothes, Pollack had worn nothing but the requisite white button-down shirt and black pants. “He showed me Calvin Klein,” Pollack recalls. “He showed me blazers! I started wearing blazers with jeans and the response I got was incredible. People started looking at me. Girls would say, ‘You look so handsome.’”

After a couple of hours of talking in circles with Sam, about whether or not he wants to be in a relationship (“some people do want a relationship, and some people don’t want a relationship”), about his dating experience (“I don’t know how you define that”), and about whether or not he’d like to just have some sex—OK, that one was my question (“That’s hard to answer because the answer has a lot of implied meanings”), Irenstein leads him out into Union Square to talk to some real live women.

We stand outside Barnes & Noble, watching the people pass. Irenstein points to a woman sitting nearby, engrossed in her BlackBerry, and starts feeding Sam lines: “Tell her you’re waiting for somebody and that it looks like she’s waiting for somebody,” Irenstein suggests. “Say you can babysit each other for 5 minutes.”

With his relaxed posture and easy smile, Irenstein could pull off a line like that no problem. But Sam hesitates. With his hands shoved deep into his pockets, his refusal to hold eye contact, and his man purse, he’s likely to bomb.

“If you think so much,” Irenstein says, “she’s gonna be gone. Go.”

Sam wanders toward her, stops, loops back around and returns to us to report that she’s wearing ear buds.

“She’ll take them out!” Irenstein says, pushing him back toward her.

Sam approaches the girl again, and says something to her that causes her to look up briefly before returning to her phone. Sam stares at her for a second, his arms hanging at his sides, before sitting beside her and gazing into middle distance, as if he’d always planned to sit right there because where else would he sit? Eventually, Irenstein walks over and rescues him.

Of course, approaching a stranger and engaging her in conversation takes a degree of self-certainty, a sense that you’ll remain basically intact if rejected. But Sam is a man who, half an hour earlier, couldn’t tell Irenstein what his favorite color is, what his favorite food is, or what kind of weather he likes. “Do you exist?” Irenstein shouted at him. “You need to exist!” When Sam started to argue with him, Irenstein interrupted, “Don’t argue with me! Do you understand? I was like you!”

But Irenstein is not giving up: “People who leave the religious community are very strong,” he tells me. “It’s very hard to do. But once they’re out, they use that strength to move on. To move forward.”

“You’ve got a lot going for you,” he tells Sam. “But you have work to do. It starts here,” he says pointing to his head. “You have to fix what’s in here.”