Bill Ackman’s 'May I Meet You?' Pickup Plan Flops Spectacularly

Bill Ackman’s 'May I Meet You?' Pickup Plan Flops Spectacularly
Photo by Chris Li on Unsplash

KEY POINTS

  • •Bill Ackman tweeted on November 15, 2025, recommending 'May I meet you?' as his youth pickup line.
  • •His advice was mocked online but acknowledged by some experts as a decent conversation starter.
  • •Experts say the line only works if you're already tall, rich, and good-looking, which Ackman technically is.
  • •Reddit’s r/seduction suggests genuinely having interests and hosting events beats trying awkward one-liners.

In a plot twist that sounds like a hedge fund manager crashing a 2007 VH1 reality show hosted by a featherboa-rocking PUA named Mystery, Bill Ackman, Pershing Square’s bigwig, confessed he used the cringe-worthy pickup line 'May I meet you?' back in his youth. Posted November 15, 2025, on X (because why not fast-forward flirting advice?), the tweet triggered a meme storm roasting Ackman’s line as either charmingly awkward or an exclusive club for the tall, rich, and handsome. Dating guru Zachary Zane called it a 'solid icebreaker,' but Cerca CEO Myles Slayton warned this verbal Swiss Army knife won’t cut it. Meanwhile, Reddit's r/seduction recommends leading with hobbies and events—basically, be a normal person—not a walking AI pickup script.

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Source: Businessinsider | Published: 11/17/2025 | Author: Katie Notopoulos