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Game On, Part 2: The Ageless Art of the Pick-Up

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Yesterday, NYU senior Jesse VanDusen introduced his grudge match for the ages: pitting the dating advice of 16th century courtier Baldassare Castiglione against the notorious ‘Pick-Up Artists’ of our own day. As yesterday’s episode concluded, VanDusen was about to move in for his first attempt to chat up women using pricey modern techniques…

By Jesse VanDusen

Sprezzatura

I introduced myself to the two girls racking up their Verizon bills with a technique Luna aptly calls the “opinion opener.” I said that a friend of mine was debating moving from Brooklyn to Manhattan, and I wondered which borough they thought was cooler. They looked up from their phones with dazed grins — it worked.

The pair had recently graduated from the New School with degrees in fashion design but I didn’t really care. In order to assert my higher status I had to constantly one-up their achievements. They had graduated with one degree; I’m graduating with two. They’ve never been to McSorley’s; McSorley’s is my spot. I bombarded them so quickly with boasts they didn’t even have a chance to comment on my silly ski hat.

But this lasted only so long. While trying to explain exactly how many Michelin-ranked restaurants I had eaten at in Europe last year, an unruly bunch of Wall-Streeters stepped in. The sheer number of the men undid me — the two women quickly jumped ship and I was defeated.

What went wrong? I peacocked. I opinion-opened. I inflated my ego like a Macy’s Thanksgiving Parade balloon. Two days later, I visited Luna’s two-floor brownstone on the Upper West Side and find out. The apartment, which he shares with the vice-president of his company, 21-year-old Miles Bukiet, is where Craft of Charisma holds its $3,500 mastery course.

“Your problem is you had to make those other guys look like a bunch of assholes,” says Bukiet, who is on leave from Wesleyan College to work for Luna. Nearby, there’s a salad bowl filled with every size and flavor of condom money can buy.

Luna, tall with greasy black hair and a flat sweaty face, lies stretched over one of the two black leather couches that face a 72-inch Samsung flat-screen. As Miles explains how I could cut down my financial district foes, Luna butts in, throwing up his hands with what seems like unadulterated panic.

“No, that’s not the way to do it at all,” Luna says. “You have to befriend the guys. At the very least you’ll make some new friends at the bar and be more social.”

Bukiet then heads upstairs to prepare for a session he and Chad Richardson, a short Colombian man in his late thirties who asked to be renamed for this article, will be teaching tonight.

Before taking Luna’s private dating lessons, Richardson suffered from social anxiety. Six months and $12,000 later, Richardson can game his way to your heart (or at least your telephone number). He attributes his success to a cult-like adherence to Luna’s rules. “I bought this shirt I call the Captain Crunch shirt because it looks like the silly thing Captain Crunch wears,” Richardson says. “I did it because Chris told me to and it works, even though I think I look ridiculous.” Richardson freely volunteers to run classes like the one with Bukiet tonight.

Luna won’t be teaching — a supermodel asked him to attend an Iranian symphony at Carnegie Hall.

I had other plans for the evening as well. I was going back to McSorley’s sans chapeau and sans ego. Unlike gamers like Luna, my 500-year-old friend Baldassare Castiglione insists that a man “Not cracke and boast of his actes and good qualities.” Boosting higher social power was out — the man with sprezzatura knows his strengths but rarely shows them, especially not during a first encounter. I also replaced the winter hat with a new fashion formula. Apparently, for the perfect courtier conformity was all the rage, blending in with the common folk like Prince Hal in Shakespeare’s Henry IV trumped flamboyant individuality any day. In fact Castiglione says a man should “fashion his garments after the faction of the most, and those to be black or of some darkish and sad coulour, not garish.”

So I sat at another round table of McSorley’s dressed almost entirely in black, looking somewhere between a die-hard Parisian and a 15-year-old My Chemical Romance devotee. This time I didn’t even need a gimmicky opener (Castiglione provides none in his book). Leaning my wooden stool way back I accidentally bumped heads with the girl sitting behind me — somewhere the Elizabethan gods were smiling. I apologized and started conversation with the beautiful curly-brown haired NYU junior. At every opportunity I complimented her — on her outfit (silky grey shirt), on her job (an internship with a commercial production company), on her smile (it was a great smile.) And at every occasion I shirked away from revealing much about myself — I never boasted about the heights of my academic achievements and I never mentioned my own employment or lofty aspirations. I just sat like a courtier, listened, praised and blended in.

By the end of the night I had a phone number and a bursting grin of my own.

And the first round had clearly gone to Castiglione.

Tomorrow in Part 3: The art of the kiss

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