It has come to light that Bill Ackman’s recently viral conversation starter—now circulating widely across social media platforms—was more than just a clever line; it was, in fact, one of the strategies he reportedly used to introduce himself to women during his college years. Whitney Tilson, who once managed a hedge fund and more recently made a bid for the office of New York City mayor, has known Ackman since their shared days as Harvard undergraduates. In an interview with Business Insider, Tilson recounted that, during Ackman’s time as a bachelor, he often heard of his friend’s remarkable success employing a short, direct question that has lately found renewed attention online: “May I meet you?”
Tilson clarified that, although he had never personally witnessed Ackman delivering the line in real time, he clearly remembered Ackman describing its use with evident amusement and pride—particularly in contexts as unglamorous and spontaneous as the New York City subway. In Tilson’s view, the story captures Ackman’s essence perfectly. “That’s Bill,” he stated, emphasizing that such behaviors were entirely in keeping with Ackman’s character. “He’s naturally bold, unapologetically straightforward. If you know his trajectory as an investor, you understand that he embodies persistence and tenacity like few others I’ve met. He’s never been afraid to take risks or to expose himself to criticism.” Tilson, who later shared the anecdote on Facebook, explained that Ackman’s willingness to be candid and proactive—traits frequently seen in his business dealings—was equally visible in his personal approach to meeting people.
Interestingly, Tilson said he could not recall any instance in which Ackman confessed that the line backfired. Then again, Tilson was quick to concede that his friend enjoyed certain advantages that might have contributed to its effectiveness. As many social media commentators have also noted, Ackman was already tall, good-looking, and self-assured even before his meteoric rise on Wall Street. Today, Ackman, married and the father of several children, is estimated by *Forbes* to possess a net worth of roughly $9.3 billion—an impressive testament to a lifetime of strategic confidence.
Although Tilson admitted that he had not recently discussed the viral post with Ackman, he speculated that Ackman himself probably never anticipated the degree of attention it received online. “It’s rather harmless when you think about it,” Tilson remarked, suggesting that the internet’s fascination likely stemmed from the sheer simplicity and boldness of such an unadorned introduction. Business Insider contacted Ackman for a response regarding the resurgence of the story, but he did not reply to the request for comment.
Tilson, for his part, has had a distinguished career of his own in the financial world. He operated Kase Capital Management for nearly twenty years until closing the firm in 2017, after which he continued to influence the investment community through writing, teaching, and media appearances. Regarded as a dedicated advocate of value investing, Tilson co-authored *The Art of Value Investing* in 2013, a publication that helped solidify his standing as an authority in the field. His commentary has made him a familiar figure on various financial news networks, where his insights on markets and investor psychology remain in steady demand.
Their professional paths intersected notably in 2012 when Ackman took a public short position against the nutrition company Herbalife—a controversial move that divided the investment world. Although many prominent traders chose to bet on the opposite side of the trade, Tilson aligned himself with Ackman, likewise shorting the stock, demonstrating both collegial support and shared convictions about market fundamentals.
Reflecting further on their student days, Tilson reminisced that Ackman had several romantic relationships during college and possessed a certain pride in bringing people together, often playing matchmaker for friends. Tilson himself, though intrigued by the charm of Ackman’s conversational daring, confessed that he never personally attempted to use the now-famous line. Still, he concluded with a note of approval: confident, composed, and courteous as it was, he considered it a surprisingly effective way to initiate genuine human connection.
Sourse: https://www.businessinsider.com/bill-ackman-college-friend-whitney-tilson-pick-up-line-2025-11
