Billionaire’s Unorthodox Pickup Line Divides The Young, The Lonely And The Single

Billionaire Bill Ackman is dividing the internet due to a highly unorthodox pickup line.

On Saturday, Ackman acknowledged the struggles of young people meeting potential romantic partners in real life, as opposed to on a dating app, and suggested they use a pickup line that has worked for him. (Subscribe to MR. RIGHT, a free weekly newsletter about modern masculinity)

“I would ask: ‘May I meet you?’ before engaging further in a conversation. I almost never got a No. It inevitably enabled the opportunity for a further conversation. I met a lot of really interesting people this way. I think the combination of proper grammar and politeness was the key to its effectiveness. You might give it a try,” Ackman said.

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

Ackman later followed up and said he had received a positive success story using his line. However, it didn’t go so well for others.

Feedback from the field https://t.co/3PHHvvaQKG pic.twitter.com/x9NRe0xz5J

— High Yield Harry (@HighyieldHarry) November 17, 2025

I tried this at the coffee shop.

I asked this cute girl sitting next to me, “May I meet you?”

She said no.

The end. pic.twitter.com/TzDTNxmkSj

— Heisenberg (@Mr_Derivatives) November 15, 2025

I just tested @BillAckman’s “May I meet you” dating method https://t.co/scDdaMLuMi pic.twitter.com/3nv5U5ghHN

— Nick O’Neill (@chooserich) November 16, 2025

Unironically, “May I meet you” has just become a killer pickup line for this exact demographic

– gets a laugh
– inside joke creates shared connection
– signals interest with low pressure https://t.co/Y15OEhT0Z7

— Lulu Cheng Meservey (@lulumeservey) November 17, 2025

Some women actually praised the line, arguing that if it has already become an inside joke among, presumably, people who work in tech or finance, live in New York City, or just follow Ackman and the viral discourses of X.

some dude in a bar in west village tonight is going to say “may i meet you?” and it’s going to work on some girl. they’re going to get married. they’re going to have 5 kids and a golden retriever in greenwich, ct. the end. https://t.co/GNBZqcRioQ

— Aubrey Strobel (@aubreystrobel) November 17, 2025

Pickup lines are all about the delivery and who’s delivering them. Of course, if you are tall, handsome, and signaling wealth, you can get away with a much cheesier pickup line. If you are an Average Joe, your pickup lines need to be clever enough and smoothly delivered to get the woman to laugh and feel at ease.

It’s also about the context. Ackman’s “May I meet you?” could work if the person is online enough to be aware of the trend. However, if you are in a dive bar in Wyoming, “May I meet you?” might not pass muster. Frankly, I don’t think “May I meet you?” would have worked on my wife.

The only advice I would give is to embrace the Silicon Valley mantra of failing fast and failing often. If someone doesn’t express interest, don’t linger. Don’t be weird. Move on. And failing is sometimes fun. A night out marked by repeatedly botched pickup lines and the ensuing reactions from women makes for a far better story than a night quietly lingering in the corner of the bar amongst your friends. Also, having a wingman makes it easier (and more fun), as well.