A Portrait of the Pickup Artist as a Young Man

With women way past liberated and our collective libido in hyperdrive, it’s a glorious time to be a guy. For the desperate ones not getting any, though, the shame has never stung worse. Fortunately for them, seduction guru Vin DiCarlo has the solution to loserdom, at just two grand a seminar.

Late Sunday afternoon, we get to the sex part.

Vin DiCarlo stands at the front of the room in a tight blue T-shirt and artfully tattered jeans, walking us through the final steps of the DiCarlo Escalation Ladder.

“I’m not going to tell you guys anything technical about kissing,” he says. “But after kissing her, what I’ll do next is move to kissing the neck. Okay? Kissing the neck.”

He strokes his throat softly, just under the jawline, like he might if he were alone with a woman. But there is no woman. It’s just us. Eight guys: five students, two assistants, and Vin, who says he’s slept with more than a hundred women, many within hours of meeting them.

“Once you get to that point,” Vin continues, “the next logical move would be to put your hands on her back.” From there, he swiftly progresses down his hypothetical girl’s body, first lifting her shirt “so your bare stomach touches against her stomach,” then “incidentally stimulating her vagina, through her clothing or whatever,” then removing her clothes, and eventually moving to full-on sex.

The room sits in silence. We’re all hung over and worn down from three days of hard-core training. During this weekend-long DiCarlo DiClassified workshop, we’ve gone over all the techniques for picking up women. We’ve done practice drills, and even gone out “into the field” to put our new skills to the test. Now we’re spent, and I’m staring at my notebook wondering what the hell I’m doing here listening to this 28-year-old “seduction guru” explain the elements of foreplay. I feel pathetic.

But I can’t not listen to Vin. It’s dirty, sleazy, repulsive. And yet: I’m hooked. He’s got something irresistible, and I can’t seem to dismiss all this as just testosterone-fueled ego-pumping bullshit for the post–sensitive ’90s man. Vin may have begun life as a hapless can’t-get-laid geek, but he’s become a real charmer. Charisma, you might call it. Or presence. Whatever it is, he’s got it. And that’s why, fried as we are, we’re still sitting here, lapping up his mojo: He’s promised us that if we listen to him, we can get it, too.

Seductionism, and the industry surrounding it, is all about sex. It sprang
up, unsurprisingly, in the early days of the Internet, which, as you may have heard, has revolutionized the way we think about sex a lot more than the Kinsey Report ever did. With girls going wild all over the place, the hard-up guys downloading porn day and night were left to ponder just one thing: How come I’m not getting any? Into this Zeitgeist strutted early seductionists like David DeAngelo and Ross Jeffries, who was reportedly the model for Tom Cruise’s character in Magnolia. Blending Don Juan mysticism and social psychology reminiscent of business books like Getting to Yes and The Art of the Deal, these visionaries came up with a set of strategies that promised to make it easy for anyone—absolutely anyone—to get lucky.

Over the next decade, seductionism became a movement, complete with books, websites, DVDs, and training classes like the ones Vin puts on—all of them aimed at men who are, as Diggs, one of my fellow students put it, “sick of not getting laid.” The Dr. Phils of the world keep insisting that men are emotional creatures who just want to be held, but the truth is we’re ruled by our carnal ambitions. More than money, fame, or power, more than anything, a man with the ability to score beautiful women has it all.

And that’s what led Vin into seductionism: He never got any, either. “Man, I was such a loser,” he tells me the first time we meet. He is smiling at the image of his old self. “When it came to dating, I was a failure—I mean, a total failure.”

It’s a Saturday afternoon a few weeks before the seminar. We’re at the Starbucks in Copley Place. (The mall is a favorite pickup spot for Boston seductionists, who calculate that women out shopping on a Saturday afternoon keep their guard lower than when they’re at a nightclub.) We’re joined by Alfredo Gutierrez, who Vin introduces as his personal manager. Alf’s a 21-year-old business student at UMass Boston and a Vin disciple. He’s decked out in a black suit and a wide-collared white shirt with a black tie. “He was a virgin when he came to me,” Vin confides when Alf runs off for cream and sugar. “You should see his girlfriend now. She’s totally hot.”

It’s not entirely clear why Vin needs a personal manager—“Alf deals with my travel arrangements,” he explains vaguely—but it does fit the playboy image Vin has spent years cultivating to cover up what he used to be. Today, he comes across as a less perfect Johnny Depp: narrow face, scruffy swashbuckler’s goatee, bucktoothed smile. He makes eye contact when he speaks and has a calm, languid way of moving that seems copped from Richard Gere in American Gigolo. At the same time, there’s a femininity to his strut, and his slickster wardrobe doesn’t come close to the sophistication of Gere’s Armani suits.

Vin grew up in Portland, Connecticut, a dot of a town in that blank space between Hartford and New Haven. He spent most of his time studying, painting, and playing guitar. An “alt” background like that should’ve made him a high school stud. Instead, it came off as artsy bookishness that alienated him from his peers. “I was a nerd, into physics and music and stuff, so I was a virgin till my last year in high school,” he says. That seemed to cement his loserdom, and much as he would later in life, he devised a strategy to rectify the situation. “The only reason I lost my virginity is that I went for someone who was known to be really easy. That’s what I had to do.”

After high school, he studied physics at the University of Connecticut, and continued to have little success with women. The physics department wasn’t exactly overflowing with babes. And the one girlfriend he did have cheated on him. “I swore I’d never feel like that again,” he says, glancing at Alf as if reinforcing some lesson, as if to say, And don’t you ever let yourself feel like that. Soon after graduation, a friend introduced Vin to a cute woman who had recently arrived from the Philippines. She was nice, not the cheating type. He married her. “That lasted about six months,” he says, shaking his head.

Vin was 22, divorced, living in the dreary western Mass. town of South Hadley, and miserable. His 9-to-5 at an engineering firm bored him. A few months later he quit, hoping to devote more time to the rock band he played in. To pay the bills, he started a janitorial business, taking a cue from his father, who’d owned a cleaning company for years. “I drove a white van,” he recalls. “This wasn’t a pimped-out 1970s van, with a disco ball and a Nintendo and a bed in the back. This was a cleaning van, with cleaning equipment and chemicals and things that probably gave me brain damage.”

Vin was desperately lonely. So when he heard a story about a guy who had a trick for picking up girls in 10 minutes, he decided to find out more. After some online research, he discovered Ross Jeffries, founder of the “Speed Seduction” system. This was what he’d been looking for, what he needed. As always, he studied hard, reading the work of other pickup pioneers, particularly David DeAngelo, whose 2001 book, Double Your Dating, is a seduction bible. He downloaded scripts—not just pickup lines, but entire conversational threads designed to keep the dialogue open and moving toward sex—and became a devotee of an Internet discussion group called alt.seduction.fast. After learning about the existence in other cities of seduction “lairs” that convene to discuss pickup techniques, he formed a chapter in Boston. The first official meeting was on a freezing day in late 2003. Vin and a few online friends went out together near Faneuil Hall.

“These guys were other nerds,” Vin says, laughing and taking a sip of his coffee. “They had sheets of paper with what they were going to say. I was the only one who didn’t write anything down. I thought I was fucked. I thought these guys were going to get laid the first night because they knew exactly what to say.”

It turned out Vin was the only one who “closed”—he got a phone number. “I was a natural.” A week later, he says, he slept with the girl. He was hooked. He became obsessed with “doing pickup,” and eventually quit the band because he didn’t have time to rehearse. He expanded the Boston lair and began writing about seductionism, quickly building a reputation on the Internet. His quasi-academic approach was in opposition to the mysticism and “natural game” of most gurus. His assertion that seduction was a structured process fit perfectly into the social calculus of his audience.

By early 2005, Vin was ready to go pro. He and a friend from the Boston lair founded a seduction training company called TheApproach and began offering boot camps in Boston and New York. The sessions were an immediate hit, with clients paying upward of $1,600 a pop. TheApproach was soon staging workshops in cities from San Francisco to London.

Vin had made himself a seduction guru. “Pickup was something that took me from being unhappy to finding happiness,” he says. “I found validation in this.”

The first day of the DiCarlo DiClassified Drills seminar falls on a cold, blustery Friday in February. We’re crowded into a drab function room in the basement of a restaurant in the Financial District. (I’d love to reveal the restaurant’s name, but Vin asked me not to, for fear of giving away information to his competition.) I’m a little nervous.

“This isn’t the type of workshop that’s for generally making your social life better,” Vin says in his opening remarks. “That’s going to happen, but what this is, is hard-core pickup training. Because you’re here, you’re going to have no choice but to change.”

My classmates aren’t the slick mini-Vins I expected, but instead a mishmash of desperate, insecure souls. Brian, a tall, redheaded 25-year-old who has flown in from Lansing, Michigan, got into seduction after a longtime girlfriend broke his heart. Bob is a young, loud Web designer from Rhode Island with a little paunch he hides under baggy button-downs. Diggs is a stocky pre-law student at BU with a perpetually confused look. Rahul, a 26-year-old immigrant from India, is the most unsure of all of us, and the only one who asked me not to use his real name. He works in high tech and wears designer jeans and a ridiculously oversize watch around his thin wrist.

“Pickup,” Vin says, pausing midsentence for effect, “is easy. People think there’s a lot of mysticism in it, or that it’s this larger-than-life thing. It’s not. All that stuff is just an illusion. So what I’m doing is changing your belief system.”

The drills that make up Vin’s curriculum are meant to get his acolytes climbing the “Attraction Hierarchy.” It’s a progression shrouded in the kind of indecipherable pseudo-intellectual jargon that self-help gurus of every stripe have employed for centuries:
1. Warm Dominance: To possess a steadfast emotional state that is completely independent of transitory social interactions.
2. Intrigue: To withhold your power on some level, whether it be holding back information, compliance, or direct indications of your interest.
3. Connection: Showing a promise of something that is directly valuable to a woman.
4. Credibility: What allows a woman to trust you. First, she should feel that you are safe and trustworthy. Second, she should feel a bit connected to you. Third, you should be able to give her direction.
5. Leadership: The state of being in control of the social situation and producing certain outcomes through perceiving and exploiting windows of opportunity.

In short, the Attraction Hierarchy translates to this: Don’t be desperate. Be yourself. Be charming. Be unafraid. Solid advice, if hardly the kind of top-secret stuff that would justify the seminar’s $2,000 price tag.

For the first drill, I am paired up with Rahul. We’re supposed to hold eye contact for five minutes, which will help us become accustomed to “confronting” a stranger. It’s basically a staring match. It turns out I’m pretty good at this, mainly because I know I have nothing to lose. I’m not “in the field”; no one is going to reject me here. My ego is safe.

But Rahul has trouble. He can’t hold my gaze for more than a few seconds. Each time we try, he breaks it off, titters in embarrassment, and says, “Damn. Okay, sorry, let’s try it again.” He takes a deep breath. Rubs his sweaty palms on his thighs. Exhales. “Ready,” he says, and we repeat.

Over the next two hours we take in all kinds of useful tips about approaching women. Apparently, I’ve been doing it wrong my whole life. For instance, I should have persevered through the various rejections I’ve heard over the years, such as “I think the gay bar is down the street.” Rather than retreat, Vin says, I should come back with something like, “Yeah, I hear it’s a lot of fun down there.”

After covering the basics, we’re ready to take things to the next level and learn what to do when we get our first taste of success—like when a girl actually agrees to talk to us. “If a girl gives you a compliment,” Vin says, “it’s a huge indicator of interest, so it’s also a huge window. So what you want to do is escalate.” He pauses to see if we’re grasping what he’s saying. “Now, excuse the homosexuality of what I’m about to do,” he continues, raising his eyebrows suggestively, “but you’re all going to do it, too.”

He motions to Diggs. “Okay,” Vin instructs, “give me a compliment. Tell me I have nice eyes or something.”

Diggs shifts his weight from one foot to the other. His gaze wanders for a second, checking to see what the rest of us are thinking. Finally he gestures vaguely toward Vin and mumbles, “You have nice eyes.”

“Really? You do, too,” Vin replies immediately. At the same time, he reaches his arm around Diggs’s waist and pulls him close, hip to hip. Like a great actor, Vin flows so authentically that in that moment, we almost believe he’s seriously hitting on Diggs. He tilts his head to make eye contact and smiles.

After an awkwardly long moment, the smile becomes a smirk and Vin releases his unnerved prey. He comes out of character and turns back to the class. “You want to train this,” he says. “It’s very important for a man to know what the appropriate escalation is for what a girl is doing. Okay, so give it a shot, guys.”

A few seconds later, I find myself wrapping my arm around Daniel Rose, a thin 21-year-old BU business student wearing a stenciled sports jacket and spiky hair. He is one of Vin’s guest lecturers and author of a self-published guidebook titled The Sex God Method. “I love your laugh, too,” I tell Dan as earnestly as I can, leaning in for the waist grab. Vin, hovering over us like a coach watching his players, nods his approval. “Good,” he says. “Good escalation.”

The seduction scene remained largely confined to the underground and the back strands of the Web until 2005, when journalist Neil Strauss published The Game. Documenting the real-life exploits of a seductionist named Erik Von Markovik, the book made the New York Times bestseller list and topped the Amazon.com rankings. Suddenly, seductionism was in the mainstream. Von Markovik, who goes by the nom d’amour Mystery, became a lecture-circuit celebrity and began running “Mystery Method” boot camps to turn Average Frustrated Chumps (AFCs) into Pick-Up Artists (PUAs). A film version of The Game is reportedly in the works.

If the movie ever comes out, Vin will probably go see it, but he suspects he won’t like it. Though he says he knows Mystery personally, he’s not impressed by his method. In the introduction to a 2006 Internet essay titled “Structured Natural Game,” Vin took a swipe at him while panning Strauss’s book, writing, “Highly reliant on canned material and routines, early seduction methods…created men who became robotic, lifeless, and emotionally inept. You can read all about them in The Game.”

The teaching of seduction, Vin argues, is in need of a total overhaul. This has become his obsession. Despite his own penchant for self-aggrandizing psychobabble—the “Attraction Hierarchy”?—he believes his workshop is a counter to everything that’s wrong with the current pedagogy. Today, pickup theory and scripts are in wide circulation online, and the various training seminars that exist are really just long lectures followed by a demonstration by the guru at some local bar. But DiCarlo DiClassified isn’t mere theory, he insists: It’s applied seduction. No scripts. No demonstrations. In Vin’s system, training has to be hands-on and done in real time, to replicate the interactions and nervous energy of an actual pickup. “Imagine soccer practice was just some coaches talking in front of a classroom, versus a team that practices and runs and shoots on the goal and actually does different drills,” he says. “It’s a world of difference.”

Friday night, a few hours after day one of our DiCarlo DiClassified workshop lets out, and the streets of the Theater District hum with cars and slinky women in little black dresses. The bouncer stamps our hands and ushers us into the Underbar, a glitzy nightclub beneath the Roxy. We’re here to test the concepts we learned in the classroom, and ourselves.

We’re not very good. We do a lot of standing around and watching pretty girls walk by. Vin tries to introduce Bob to several prospects, but Bob doesn’t persevere through their rejections. Rahul winds up sitting on a couch alone. Even Daniel, the Sex God author, stands off to the side, inert.

Brian eventually starts talking to an attractive Asian girl with a long face and big eyes, a sort of prettier Margaret Cho. He’s got her laughing at his jokes, and manages to wrap his arm around her waist. She giggles and squirms for a second but doesn’t push his arm away. “He’s doing really good,” Vin shouts over the music. He watches quietly for a moment, not unlike a father watching his son ride a bicycle for the first time, and then wanders off to see how everyone else is doing.

It’s impossible to tell if Vin is proud of Brian or proud of himself for helping Brian. To be honest, even after the seminar and after reading Vin’s writings and talking to him several times, I’m unsure about a lot of what he is up to. My over-educated side wants to mock him mercilessly as a charlatan. After all, despite Vin’s criticisms of his competitors, there’s a strong element of same-crap, different-system to DiCarlo DiClassified: A DVD is in the works, and Vin’s convoluted mumbo-jumbo is as pedantic as anything Mystery or Jeffries is peddling. Seduction guru? Maybe more like bullshit artist.

At the same time, I can’t just write him off. Sure, seductionism makes me glad I don’t have a daughter running around out there. But, ultimately, Vin’s lessons aren’t any nuttier than those of more culturally accepted “gurus” like business legend Tony Robbins, or fitness freak Richard Simmons, or even damn Dr. Phil. In his own way, Vin’s a very serious thinker who spends his days refining his craft. He’s not merely interested in getting laid or helping other men get laid; he’s obsessed with finding a better way to teach men how to get laid so that no man will ever feel the way he once did—like a nobody.

This is every guru’s great trick: that anyone can do it. Vin is exploiting man’s biggest weakness—himself—and milking it for everything it’s worth. My classmates and I know he’s doing it, and yet we let him. He has seduced us. But only because we want to be tricked.

“Before a guy has any skills, he just wants to get laid. He just wants women,” Vin tells me during one of our final conversations. “But what that is, is an unfulfilled emotion that getting more sex, getting more women, isn’t going to fulfill. I didn’t realize till later that this actually gives you the ability to figure out what you want out of life.”