Backstory: The Casanova class

The problem during most of their dates, he explains, was that the women never really knew what the men wanted from them. Is your interest romantic? Do you really find me attractive? The SOI should make it clear, and it is as simple as telling them, for instance: "Wow, not only are you funny and intelligent, you're really sexy, too."

But De la Vega emphasizes that while the boot camp could explain the principles of good conversation and wooing, if the men become methodic, formulaic, or insincere, they will fail. And part of being sincere is embracing their weaknesses, and not being afraid of them.

"A really strong person isn't a person who's perfect," he says. "It's the person who's comfortable being imperfect. It's a person who's comfortable expressing his limitations.... He's comfortable being in a situation in which the outcome is unknown. And just saying, 'Hey, this is how I am,' and whether she rejects that or accepts it – it doesn't matter."

***

After five hours of instruction and role-playing, the group prepares to head out to a rooftop bar in the Flatiron District in Manhattan. The next day, they would go to a Barnes & Noble bookstore to work their "day game."

The first night was anxious for most of the group. While many did find the nerve to approach women, real progress came the second day. The coaches followed the recruits, instructing them to approach different groups of men and women and strike up conversations.

Charles walked up to a woman browsing the fiction section at Barnes & Noble. They talked for almost 45 minutes. Though Charles found her attractive, he never escalated the conversation into something more. When he told his coach what happened, he was immediately told to find her again and ask her out for coffee.

"I was going to make up a story about how my friends decided to stay a while longer, but he told me just to be honest," explains Charles to the group on Sunday. "So I told her my friend said I should ask you out for coffee. She said, 'OK.' " They had coffee at a nearby shop, and ended up text-messaging each other all evening.

Jay didn't have much success his first night out. His conversation felt forced, and, besides, he was nervous. But, feeling more relaxed the second night at the rooftop bar, he approached an attractive woman wearing a dark jacket with big brass buttons – it seemed 18th century and interesting to him. "Hi, I'm Jay," he said, as he recalled the conversation later.

"Hi ... Karen." He shook her hand, warmly.

"I love your jacket! I've never seen anything like it!"

They began to talk, and eventually struck up a conversation about art and architecture. Jay smiled and laughed. He lightly touched her elbow during a moment of levity. After about 45 minutes, Jay made his SOI. "Wow, not only are you so smart, you're sexy, too."

Karen blushed, and then lighted up, smiling. She leaned in, and said, "Really?"

As they continued chatting about architecture, the topic altered a bit. They talked about the eggs and darts on moldings, and other fertility symbols adorning Art Deco buildings. Later, they walked out onto the terrace for the view and a little privacy.

This time, Jay told the group the next day, his date didn't turn away when he tried to kiss her.

Page: 1 | 2