“Why do I have to like bars?” Sara asks her dating coach, Israel Irenstein, as the three of us walk down the Bowery in Lower Manhattan toward Phebe’s Tavern and Grill. Sara, who three years ago left her husband, and three weeks ago decided once and for all that there is no God, doesn’t fit the profile of a divorcée on the prowl: She’s 22 years old. Her baggy sweater hides her figure. She doesn’t drink. Oh, and she’s never had a conversation with a secular man.

“You don’t have to do anything,” Irenstein tells her.

Glib as that sounds, his response reflects his experience. He’s used to the ex-Hasidic women he coaches inquiring about “rules”: “If I go on a date with him, won’t I have to sleep with him?” “What should I do?” “Don’t women have to dress up to go out at night?”

“They’re raised to do what they’re told,” Irenstein tells me. “They always did whatever their husbands and rabbis said. I try to teach them that secular life is about doing what you want, not what you’re ‘supposed’ to do.” In Sara’s case, bars are key to absorbing the lesson. “She has this image in her mind of what ‘bars’ are. But bars are a vital part of secular life. They’re a big part of dating.”

Last month, I wrote about Irenstein’s efforts to help Sam, a 29-year-old ex-Orthodox Jew, navigate the secular dating scene. Irenstein taught Sam basic facts about women and encouraged him to work on his self-image. Within the OTD (“Off the Derech” or ex-religious) community, Irenstein helps roughly five times as many men as he does women. Many OTD women have been raised to obey, to take a back seat, and to avoid speaking to men, so they are less likely to ask for help with their love lives. As a result, they often struggle once they’ve left the fold. The women Irenstein meets through Footsteps, the nonprofit that helps OTD’ers assimilate into secular society, are “miserable and alone, or they sleep with a million guys, or they settle for the first guy they meet, often another OTD’er.” When women do reach out to him, Irenstein is thrilled to help.

Sara grew up in California in one of the strictest Hasidic sects, where she learned that bars, public schools, non-Jews, and even Jews from other Hasidic sects, were to be avoided. At 18, she met her future husband for one hour. Then they married. Because she was entirely uneducated about sex, sleeping with her husband was so repulsive and frightening to her, she could endure it only a few times. After that, she spent months creating excuses until her husband got fed up, drained her bank account, and left her. Ostracized by her family and community, Sara realized she could either commit suicide or reinvent herself. So she saved up enough money to flee to New York.

Three years later, she has a small apartment and a job she’s not crazy about, but she’s proud of her self-sufficiency. However, she fears men, whom she associates with the trauma of her marriage. The only men to whom she so much as says hello are other OTD’ers. Even her employers, though not members of Sara’s former sect, happen to be Hasids (and her customers are women). “I’m not used to interacting with men,” she says. “It never happens. Some guys whistle at me in the street, but I’m not attracted to them. I want to meet guys I’m attracted to who are attracted to me.”

Beautiful with thick hair and long eyelashes, Sara holds intense eye contact that implies not “I’m comfortable in my skin,” but “I dare you to take me down.” Once you get her talking, she is startlingly open about the details of her life, and about how disappointed she is that she’s spent the last few years essentially alone. One of the main setbacks for OTD women like Sara is isolation—many socialize with other OTD’ers or no one at all. Because they don’t know what’s socially appropriate and what’s not, they often keep to themselves rather than risk social humiliation. They’ve done the hard work of leaving their communities, but they have no idea how to replace their old lives with new ones.

“There are things you can do,” Irenstein tells Sara. “For people like us, dating isn’t intuitive. We have to learn. People say ‘go with the flow,’ right? ‘Be yourself?’ ” He shakes his head. “Trust me,” he says, laughing, “don’t.”

“OTD women grapple with how to make social cues clear even when they’re forming new friendships,” said Lani Santo, executive director of Footsteps. “With men, they wonder how to be honest about their feelings and how to communicate when they want to be ‘just friends.’ ”

At Phebe’s Tavern and Grill, Irenstein, Sara, and I find three stools off to the side. Because it’s happy hour and one of the first warm days of the season, the bar is full of groups of friends in summer clothes, holding pints of beer. Sara admits, with some prodding from Irenstein, that Phebe’s is a nice place, but she says that she prefers to watch the action than to join it.

“Who’s cute?” I ask her. “Who’s your type?”

“No one here is cute,” she says quickly. She’s holding her purse in her lap, eyeing the people around us warily.

Irenstein doesn’t push Sara to get up and mingle. He just leans back and sips his beer, commenting on our surroundings as if he and Sara are anthropologists studying a foreign culture, which, in a sense, they are. “See all the different things people are wearing?” he asks. (Sara was just complaining that her clothes weren’t fancy enough.) “There’s a pair of shorts. Jeans. A skirt. It’s anything goes in here.”

This is the third time I’ve watched Irenstein work with Sara. The first time, he met her in a coffee shop; the second time, a restaurant with a bar scene. At each meeting, Irenstein breaks down her destructive beliefs and replaces them with more useful messages. No, she’s not too fat to date. No, it doesn’t matter that she owns no expensive clothes. No, not all men are ill-mannered pigs. She’s adorable. She looks great. People will like her.

“I guarantee you,” Irenstein says, “the guys you’re attracted to are attracted to you.”

“Really?” Sara’s eyes widen, but she insists that that can’t be right.

“People are friendly,” Irenstein tells Sara. “You can talk to them. You can go up to those people at the bar and ask, ‘How’s the food here?’ and they’ll tell you.”

“No!” Sara says, giggling, her cheeks turning pink. She pulls her phone out to check her text messages. But amazingly, Irenstein’s encouragement seems to be working. Just receiving compliments for the first time in her life has boosted her confidence; over three sessions, she’s become more talkative, inquisitive, and relaxed. Now she puts her phone away, plays with her hair, and periodically glances at the people around her.

Finally, she concedes that she’ll talk to men, but only if I’ll come with her and start the conversation. I have her choose a group for us—she points out three guys in their mid-20s wearing polo shirts and slacks—and I lead her to them. I ask them something about the beers they’re drinking and they widen their circle to accommodate us. Within seconds, they’ve pulled Sara into the conversation. As the five of us chat and joke around, one of the guys slings his arm around Sara’s shoulder. She stiffens for only a second before moving closer to his body. For the first time in her 22 years of life, she’s engaging with secular men.

When we finally break away from the group and return to Irenstein, Sara is ecstatic, trembling so violently, she drops her phone. “We have to leave now!” she squeals at Irenstein. “I’m shaking!” She laughs as she pulls him to his feet. “I can’t stop shaking!” She shows us her quivering fingers. Once we’re out on the sidewalk, she says, “I think one of them liked me!”

“What did I tell you?” Irenstein says. “Everyone will love you.”