Billionaire hedge fund manager Bill Ackman recently shared some dating advice for young men on X, and the resulting online mockery proves his dating reality is probably much different than yours. The 59-year-old investor, who is worth billions, decided to weigh in on modern romance.
Ackman’s central issue is something many of us can agree on: he feels that online culture has completely “destroyed the ability to spontaneously meet strangers.” If you’re trying to meet someone in a public setting, that spontaneity just seems gone, and honestly, he’s got a point there. However, his advice, found by Brobible, sounds like something that happens in only the fanciest settings.
His solution is where things get interesting and undeniably awkward. He shared the exact words he used during his youth to approach someone he found “compelling.” That magic phrase? “May I meet you?” This isn’t going to hit our list of best TikTok pickup lines anytime soon.
Who says this and doesn’t immediately feel embarrassed?
Ackman claimed that when he used this phrase, he “almost never got a No.” That is a bold statement. He thinks the key to its effectiveness was the combination of “proper grammar and politeness.” He then suggested that this highly formal approach should work for everyone, including women seeking men or same-sex interactions. He wrapped up his advice, which he called “just two cents,” by stating he’s concerned about the “next generation’s happiness and population replacement rates.”
That was truly all it took for the internet to go absolutely wild. If you’re going to drop a phrase that sounds like it was pulled straight from a Jane Austen novel, you have to expect some brutal feedback, especially when you’re a billionaire. People immediately started generating memes and jokes, calling the whole statement absurd.
I hear from many young men that they find it difficult to meet young women in a public setting. In other words, the online culture has destroyed the ability to spontaneously meet strangers. As such, I thought I would share a few words that I used in my youth to meet someone that…
— Bill Ackman (@BillAckman) November 15, 2025
The general consensus was that this advice only works if you already possess the inherent confidence and status that comes with being a wealthy, successful person. If a regular guy tried that, he’d probably get a strange look or maybe even be laughed at. However, we’d rather have this than hear about a celebrity who inappropriately tries pickup lines on minors.
We didn’t have to wait long for someone to test this theory in the wild. One commenter shared a very brief, painful anecdote about putting Ackman’s advice to the test immediately. This commenter wrote that they tried the advice at a coffee shop, asking a girl sitting nearby, “May I meet you?” The result was swift: “She said no. The end.” That’s rough, but it proves that not everyone is charmed by vintage formality.
Ackman doubled down and advised the rejected commenter to “Try again.” He also added a little motivational speech, telling the user, “You need not fear being rejected. Wrong girl for you. Her loss, your gain.” I agree with that, your story doesn’t end just because you got rejected. Not everyone is going to like you, so don’t feel down because someone says no. Try for someone else.
While the billionaire’s heart might be in the right place regarding the state of modern dating, his advice certainly isn’t hitting the mark. It’s definitely a funny reminder that sometimes, people who live in the upper echelons of wealth just don’t have the same social experiences as the rest of us. If you’d like to avoid instant rejection and becoming a viral meme, you’re probably better off sticking to a simple “Hi” or maybe even just a friendly smile. Skip the “May I meet you?” unless you’re auditioning for a period drama.
