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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? 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. 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. A naturally outgoing person, Irenstein learned quickly and his dating life began to thrive.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.” ).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.

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.“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’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.Pollack brought a girl with him and Irenstein pulled him aside to say, “She likes you. Since growing out of baby clothes, Pollack had worn nothing but the requisite white button-down shirt and black pants. We stand outside Barnes & Noble, watching the people pass.Kiss her.” Never having kissed a girl, he was scared, but with Irenstein’s encouragement, he went for it. Irenstein points to a woman sitting nearby, engrossed in her Black Berry, and starts feeding Sam lines: “Tell her you’re waiting for somebody and that it looks like she’s waiting for somebody,” Irenstein suggests.

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