Billionaire Roundly Mocked Over His Cringey Pickup Line: 'Some Crazy Unc Advice'

Social media users turned down Bill Ackman's dating advice after he talked up its "effectiveness" on strangers.
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Billionaire hedge fund manager Bill Ackman offered his “two cents” to young men looking to meet singles over the weekend — and social media users overwhelmingly cringed at his dating advice.

Ackman, in a post to X on Saturday, claimed that “online culture has destroyed the ability to spontaneously meet strangers” before sharing a pickup line he claimed to use on people he found “compelling” in his youth.

“I would ask: ‘May I meet you?’ before engaging further in a conversation. I almost never got a No,” claimed the Trump-backing billionaire, who married Neri Oxman in 2019 after his divorce with his first wife of 24 years, Karen Herskovitz.

“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.”

He later added that the line should work on women seeking men and “same sex interactions.”

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

A number of users on the platform tested out Ackman’s line in public while other critics mocked it, with one user calling it “some crazy unc advice” and another flat out declaring that it’s “not gonna work.”

“may i meet u” as a pickup line is some crazy unc advice https://t.co/7UrN9waBut

— John Wang (@j0hnwang) November 16, 2025

Men: don’t open with “may I meet you?”

it’s not gonna work https://t.co/hwJMvrvW2T

— Aubrey Strobel (@aubreystrobel) November 16, 2025

May I meet you? pic.twitter.com/Xapqu4Sqe2

— Murray Hill Guy (@MurrayHillGuy1) November 16, 2025

You miss 100% of the shots you don’t take https://t.co/hIO2u3Yykz pic.twitter.com/nvOD1FK0A1

— greg (@greg16676935420) November 16, 2025

Re: Bill Ackman’s “May I meet you?” advice for approaching girls.

Obviously hilarious, but also a great reminder of how far removed billionaires/celebrities are from actual society. They have zero clue how normal people interact and it’s good to remember that.

— Soho Hank (@elusivecurrent) November 17, 2025

Bill Ackman’s “May I meet you?” tweet could go down as his most viral moment since his “Hell is coming” segment on CNBC back during the March 2020 covid days…

Guy simply just knows what to say to get attention, whether good or bad.

— Heisenberg (@Mr_Derivatives) November 16, 2025

thx bill, this is "peak rizz"

just tried this at the cafe and had 7 different women call the authorities, which i understand is a common way of playing "hard to get" (i'm now banned from the cafe)

— Riley (@rylzdigital) November 15, 2025

“May I meet you?” he billionaired softly.

— saila (@sailaunderscore) November 16, 2025

The funniest thing about the "May i meet you" meme will be when it reaches such cult popularity as an inside joke that it starts to work as an ironic pickup line.

— Matt Senter (@MattSenter) November 16, 2025
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