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“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? “It communicates a leadership quality that women find attractive.” For a solo mission, Shepherd offers this approach: “You have a really nice energy. 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.Dating is supposed to come naturally, but for whom?

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. “If you could have dinner with anyone in the world, who would it be? “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. So I prioritized it.”In part, Shepherd says, they need help because they’re too honest off the bat. 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. ” If they all claim the title, which he says is likely, initiate a round of rock-paper-scissors to determine the winner.

“You have a smart girl vibe,” he says, looking at one of his students in a kind of gender twisted role-play. ”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. “In early encounters, I open up about the highlights of my life,” he tells them. 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. 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. The secret ingredient: “You’re leading this,” he says. 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.

Through video chat sessions, Toronto Wingwoman will honesty help you evaluate your past dating experiences and figure out what exactly you want and need.

Working with you we find out what barriers might be in place that are stopping you from finding love.

Or Joe*, a successful corporate executive in his early 40s who had worked so hard building his career that he’d forgotten about building a family and worried it was too late…