Backstory: The Casanova class

By the end of their third date, Jay thought it was time. The first two dates had been wonderful. Julie seemed to get him, get his sense of humor, and really enjoy spending time with him. Their first time out, he had simply driven her to work in the morning – an hour-and-a-half commute from Fort Lee, N.J., to Manhattan, which gave them plenty of time to talk. A few nights later, they hopped around to a few different places and again had a great time.

"I just thought that, you know, by the third date, I should try to kiss her," says Jay, a salesman for an international transportation company. But when he leaned over, she turned away, leaving Jay bewildered and discouraged. After his divorce, most of his experiences "out there" had been awkward and frustrating, so he wondered, "Am I just not good with women?"

Jay's bewilderment drove him to seek answers – and a better "game." So, along with six other men in their mid-to-late 30s, Jay paid $1,600 to attend a "charm school," a three-day weekend boot camp in which a cadre of young and more socially successful men would teach them the secrets of wooing women. From the art of conversation to the subtle techniques of kinesthetics – or flirtatious touching – these seven men embarked on a quest to find their inner Adonis, to learn to be desirable, and then practice their skills in the night life of Manhattan.

***

It's a Friday afternoon in Midtown, blocks from Madison Square Garden, and the seven bewildered men (who, like Jay, have been given fictitious names) are meeting for the first time with four social coaches from Charisma Arts, a company that offers these boot camps in cities across the US. Part "self-help" and part a Tony Robbins-esque effort to "unleash the power within," these seminars follow a quintessentially American ideal to apply management science to matters of the human psyche.

The men each begin with a brief introduction, describing their current plight with women. Some are funny and gregarious, others withdrawn and demure, and they vary in levels of traditional attractiveness and professional success. But each share a general sense of unease with themselves, a deep frustration and loneliness.

After Jay, a tall, attractive man with dark hair and a goatee, tells his story about his dates with Julie, Charles explains his own plight. A general practice physician who flew in from Pittsburgh, Charles, too, has gone on many dates filled with pleasant conversation, but they never go beyond that. He's well groomed, gentle, and soft-spoken – but feels he lacks the skills to attract women. Chris, an Argentine tango dancer living in Staten Island, is also a doctor in psychiatry, and despite his receding hairline, he, too, is an attractive, fashionably dressed man. He wants more choice and feels he isn't dating the kind of women that really interest him.

The others in the group include an economics graduate student at Harvard University; a computer technician from Toronto; a program coordinator from Tampa, Fla.; and a UPS driver from Connecticut. As they tell their stories, the coaches from Charisma Arts interact with them and explain problems each had encountered.

The coaches are as varied in temperament and style as the wannabe players. Chad Diego De la Vega, who takes the lead in this session, is unassuming, somewhat short, and wears glasses. Yet he exudes a calm confidence and ease. Each man has already watched a DVD and read an e-book about the Charisma Arts principles – how to establish an attractive "vibe," for example, and how to engage in personal and intimate conversation – but Mr. De la Vega wants to stress the importance of the "SOI" – statement of intent.

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.