Chris Shepherd stands at the front of a small hotel boardroom preaching the gospel of pickup artistry to six 20-something lads who have come seeking transformation.

As they feverishly transcribe his words onto hotel stationary, Shepherd, his mop of curly hair strewn, his untucked shirt peeking out beneath his sweater, speaks with Moses-like authority on the mysterious methods of girl getting.

“The belief in your head determines your actions,” he says philosophically, his fist slicing through the air to emphasize key words. “You have to be thinking that you’re worthy of her, that you have something to offer her. Otherwise, you’re giving off the needy vibe.”

The resulting nods around the table serve as an outward expression of self-reflection.

Shepherd, a real-life Hitch and international dating coach who has built a career servicing male ineptitude in the pursuit of women, holds a kind of celebrity here.

His students have converged in a downtown Toronto hotel from across the province, each dishing out a cool $3,000 for a three-day seminar with the California-based Love Systems guru, because things haven’t gone well for them in the bars, grocery stores and coffee shops where they have attempted meeting women who transfix.

Each has a tale or two of humiliating defeat.

They’re here to learn how to transform those slow-motion, train-wreck encounters into something resembling effortless savoir faire.

Shepherd, a 34-year-old Montrealer who travels the world — Sydney, London, Berlin, Tokyo, New York — teaching the mysteries of the female mind, is equipping his students with pre-prepared questions designed to fill the crucial seconds that follow, “Hey there, I’m Joe.”

Begin, he suggests, with observational intuitiveness.

“You have a smart girl vibe,” he says, looking at one of his students in a kind of gender twisted role-play. “What kind of books do you read?”

Whether such an approach actually works as advertised (unthinkable if it were uttered by me), here’s what’s clear: Shepherd delivers it with charm.

Then, he digs deeper. At least, deeper as these things are measured.

“If you could have dinner with anyone in the world, who would it be?” he directs the lads by way of illustration.

This is more art than science, he makes clear.

“Don’t ask for her resume,” he says. “It’s boring. Ask questions that get down to her character and the reasons why she’s doing things (while) communicating your own character.”

Next, he says, be prepared for the return volley of questions.

Mike, a 21-year-old university student from London, Ont., offers up basketball icon Michael Jordan as his hypothetical dream dinner mate when asked by Shepherd.

“Why?” Shepherd poses in female character.

“He’s the greatest basketball player of all time?,” the student’s voice tailing upward into a question rather than a statement of conviction.

And so begins an aimless verbal meander through nothingness, eventually leading to involuntary cringes around the room.

“The point is to talk about yourself and say that Michael Jordan is an inspiration that has meant a lot in my life in terms of becoming successful in my own life. It’s about communicating your own inner strength and character.”

More nods. The room is his.

Meanwhile, I’m pondering the more existential questions about why 20-something men who hang out on university campuses and night clubs are digging into their wallets for $3,000 to get help meeting women.

“I just needed to get this part of my life handled,” explained one. “It’s better than spending it buying drinks all night for women who disappear.”

Another said: “I’ve saved up for months to do this. It’s the most important thing for me right now. So I prioritized it.”

In part, Shepherd says, they need help because they’re too honest off the bat.

“In early encounters, I open up about the highlights of my life,” he tells them. “Probably not the problems.”

The truth, sure. But not front-loaded.

To complete the object lesson, the men break into pairs for play acting exercises with each other — an odd series of man-on-fake-woman exchanges.

Observational point: men who self-admittedly have little understanding of female reaction may not be the most reliable role-play partners when it comes to female reactions.

“Hey, there, I saw you standing over here and I think you’re really beautiful,” says a five-foot-seven business major named Doug sauntering up to a six-foot-eight computer-programmer classmate named Phil.

“How, um, is your, um, night going?”

Another coach steps in and places his hand on Phil’s arm, squeezing gently.

“You want a light touch,” he counsels. “And try to get rid of the umms. It’s sub-communication. If you stutter step, it shows hesitation.”

The other conversation killer here, Shepherd injects, is the old chestnut question about how your night is going.

Lazy. Lacking creativity. And, most fatally, predictable.

The more energized and playful alternatives include: “Let me guess. … You are getting drunk, your friend is flirting with boys and your other friend is keeping you both out of trouble.”

Or, if making the high-difficulty approach to a group of women, consider this, Shepherd advises: “Which one of you is the leader?” If they all claim the title, which he says is likely, initiate a round of rock-paper-scissors to determine the winner.

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The secret ingredient: “You’re leading this,” he says. “It communicates a leadership quality that women find attractive.”

For a solo mission, Shepherd offers this approach: “You have a really nice energy. I bet you do a nurturing job like dolphin veterinarian.”

Doug, inspired, tries again. He parrots the dolphin veterinarian line to his male partner. It’s less weird than it sounds.

But it gets worse in the following seconds.

“What’s the transition?” he pleads.

Two instructors dig into their pickup artist grab bag and pull out the so-called “opinion opener” method: Seemingly random and spontaneous questions signifying nothing but nevertheless bridging a conversation in crisis. They are questions that serve an end unto themselves.

“My buddy and I are having an argument about something and we need a female perspective,” goes one of the scripted questions.

“How long do you have to wait after you break up with someone before you hook up with her roommate?”

The answer is, of course, as irrelevant as the question. The provocation it intends to spark is the apparent point.

Shepherd spits out a few more code-red-situation savers: “Do you think people from Toronto are colder than people from Montreal?”; “Do drunk ‘I love yous’ count?”; “Is kissing cheating?”

The secret, he says, is questions that tap into the female conversational kryptonite: personal relationships.

“Nine out of 10 women will find this to be a subject matter that interests them. Women like this stuff more than guys do.”

Nine out of the 10 women I surveyed about the methodology of pickup artistry tell a far different story (it may have actually been all 10).

“I’m vomiting,” said Emma Jarratt, a 20-something journalist and single Torontonian upon reviewing Shepherd’s romance pitches. “This is categorically going to fail. As a woman who’s been to a bar in her day … just, no. This would never work.”

Megan Pratt, a 25-year-old single from Toronto, says pre-scripted pickup lines may actually be a deal killer for men seeking meaningful connection.

“Preaching that men should adopt an inauthentic, overly confident personality while making a first impression likely sets his clients up for future trouble down the line,” she says. “My concerns are primarily with his sexist diminishing of female complexity and his false advertising.”

And so, you, like them, may be among the disbelieving. Perhaps even repulsed.

But here’s the thing: A few hours later, Shepherd and his students are standing in a downtown bar surveying the options as part of the real-world training element of the boot camp weekend.

One by one, he sends the trainees into romantically charged situations, pointing out women around the room and directing the men to make the approach, armed with the skills they were taught earlier in the day.

It’s a war scene at first.

“I got shot down,” says Doug, returning slump-shouldered after an aborted mission with two attractive blondes standing barside. “It’s rough out there. They were so gorgeous. I forgot what to say.”

After several failures, the lads challenge Shepherd to show his stuff with a large group of women in the far corner who look like they may have just arrived from a magazine photo shoot.

It is inspiration.

Without a second thought, Shepherd charts a straight-line path to their table.

As the students stand breathlessly observing a few metres away, Shepherd has the group of women laughing and high-fiving him in minutes.

“He is the king,” says Doug, smiling widely. “I can’t believe it. I love that dude.”

Toronto Star investigative reporter Robert Cribb offers Mankind, a quirky video series that explores relationships, career, fashion and style, health and fitness — for men. Look for it on thestar.com. He can be reached at rcribb@thestar.ca