A dating coach for ex-Orthodox women.

Teaching an Ex-Orthodox Woman How To Date in New York

Teaching an Ex-Orthodox Woman How To Date in New York

What women really think about news, politics, and culture.
May 31 2012 12:33 PM

She’s Just Not That Into Jew

A dating coach for ex-Orthodox Jewish women.

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“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.”