I have invested far more hours than I would comfortably acknowledge delving into the curious universe of pickup artist material that has proliferated across nearly every imaginable form of media. Over the years, I have consumed television programs devoted to the subject, quietly observed heated discussions in online forums, and read an impressive range of books—some mainstream publications released by established publishing houses, others self-published or distributed as questionable e-books through the more obscure corners of the internet. My fascination with this peculiar subculture can, at least in part, be traced to the mid-2010s, when the online communities of pickup artists suddenly collided with broader political and cultural controversies. During that time, the so-called PUA forums intersected with the discourse surrounding GamerGate, a widely publicized online harassment campaign aimed primarily at women in the gaming industry, which gave these spaces an outsized and unintended political significance.
Yet my interest predated those events. Long before the GamerGate era, I was captivated by the sheer spectacle of VH1’s 2007 reality series *The Pickup Artist*. The show followed a theatrically eccentric man known by the pseudonym “Mystery” as he attempted to transform socially awkward young men into confident suitors, demonstrating his methods amid the neon haze of Arizona’s nightlife. Around the same period, I devoured Neil Strauss’s book *The Game*, a work that chronicled Mystery’s exploits and detailed the subculture’s rituals through the eyes of Strauss himself—a journalist who, somewhat ironically, evolved into a pickup artist in his own right. I found myself enthralled by this surreal world of men donning flamboyant feather boas and furry hats—what they proudly referred to as “peacocking”—all in the quest to attract attention. The combination of their awkward earnestness and the almost theatrical absurdity of their social strategies made the entire scene difficult to turn away from.
What truly intrigued me, however, was the paradox underlying these communities: the tension between the lonely, uncertain men sincerely yearning for companionship and the often cynical, manipulative, or openly misogynistic teachers who claimed to possess the secret formulas for romantic success. These self-styled gurus, who regularly marketed overpriced seminars, video courses, and private coaching sessions, developed elaborate vocabularies and intricate systems of classifications to give their advice an air of scientific precision. Despite all that sophistication, most of their instruction could be distilled into a single, almost trite message—project confidence and approach people with genuine intent.
This persistent theme resurfaced recently when Bill Ackman, the prominent hedge-fund manager and an active social-media commentator, unintentionally triggered a wave of online amusement. In a reflective mood, Ackman tweeted what he described as his long-favored opener for starting conversations with women: the simple phrase, “May I meet you?” The line’s elegance—or awkwardness, depending on one’s perspective—quickly went viral. The internet’s reaction ranged from skeptical mockery to mild endorsement. Many critics argued that such a disarmingly formal expression might succeed only for someone already blessed with Ackman’s privilege, height, or financial status, while others suggested that, coming from an average man, it would likely read as unsettling rather than charming.
Still, a subset of commentators defended the phrase as a refreshing display of politeness and directness. They proposed that, although slightly unconventional, its straightforwardness could open the door to an authentic conversation. Zachary Zane, relationships expert for Grindr, even praised the line as a “solid icebreaker,” pointing out that it invites the other person to make a clear choice—to engage or not—thereby respecting individual autonomy. Some adventurous users online claimed to have tested Ackman’s approach themselves, with at least one reporting surprising success. Yet Myles Slayton, the CEO of the dating app Cerca, remained unconvinced. He dismissed the line as ineffective but conceded that Ackman’s underlying observation was valid: men, particularly younger ones, are approaching women far less frequently than in previous generations.
Ackman’s comment taps into a broader social truth. Initiating contact with a stranger has always provoked anxiety, but for Generation Z—raised in an environment dominated by swiping interfaces and algorithmic matchmaking—the idea of starting a face-to-face conversation can feel nearly paralyzing. Many young singles lament how rare genuine in-person interactions have become, even as they express a desire for exactly that kind of connection. The uncomfortable truth is that breaking the ice requires risk and vulnerability; one must sometimes become that slightly awkward person who blurts out a clumsy line in a crowded room. The worst possible outcome is mere rejection, which, in the grand scheme of things, is hardly catastrophic.
Drawing from my own extensive, some might say encyclopedic, exposure to pickup artist tactics—nearly 10,000 hours of accumulated observation—I can confidently assert that “May I meet you?” is far from the most effective opening gambit. In the lexicon of seasoned PUAs, a successful “cold approach” relies on a line that initiates interaction naturally while diverting attention from romantic intent. For instance, a classic example from Mystery’s 2007 show involved beginning with, “Hey, did you just see the fight outside?”—a fabricated scenario designed purely to trigger curiosity and dialogue. Another effective technique for group settings was to enlist the audience’s participation: “Help my friend and me settle an argument,” followed by some lighthearted, debatable question. Such openers function precisely because they initiate conversation on neutral ground, allowing rapport to develop organically before any explicit flirtation begins.
Ackman’s phrase, by contrast, reveals its agenda too quickly. After uttering “May I meet you?” there is nowhere intriguing to steer the exchange; it immediately reduces the interaction to a transactional query rather than a dynamic conversation. Even worse, the predictable follow-up—something like “What’s your name?”—feels uninspired and overly formal. The charm evaporates as quickly as it was invoked.
Ultimately, what the pickup artist community seeks to address, however clumsily, is not the mastery of specific scripts or linguistic tricks, but the deeper psychological challenge of what they term the “inner game.” The greatest obstacle to engaging others, particularly in romantic contexts, is seldom the absence of a perfect line; it is self-doubt, fear of embarrassment, and internalized social hesitation. Confronting this barrier—learning to tolerate discomfort and rejection—is the real developmental work. Some instructors even prescribe experimental exercises, such as conversing casually with elderly women in grocery-store lines, to desensitize students to the fear of initiating contact with strangers.
Therefore, if Ackman’s peculiar line accomplishes nothing more than emboldening someone to muster the courage to speak to another human being, it has arguably served its purpose. Polite confidence—and the willingness to act despite awkwardness—constitutes most of the battle. Regardless of whether the line itself is corny or archaic, the essential success lies in taking that first small risk.
During a recent visit to Reddit’s r/seduction community—a still-thriving hub of discussion about dating strategy—I noticed that Ackman’s advice had not become a trending topic there. Instead, users were sharing a newly popular post outlining what was humorously titled a “stupid simple natural seduction method.” This post broke attraction-building down into a four-step process: first, cultivate genuine proficiency in some hobby or interest; second, organize community events or gatherings centered on that activity; third, naturally assume a leadership role that establishes social visibility; and finally, choose among those who share your enthusiasm. While the enumeration was meant to sound effortless, its underlying premise was refreshingly wholesome: rather than memorizing contrived dialogue, become a multidimensional person. Authenticity, competence, and visible passion will inevitably attract others more reliably than any rehearsed opener ever could. Even many professional pickup artists—those ostensibly wedded to the artifice of the “game”—would begrudgingly agree with that conclusion.
Additional reporting by Sydney Bradley.
Sourse: https://www.businessinsider.com/bill-ackmans-pickup-line-may-i-meet-you-effective-2025-11
