Back to episode — Episode 3020 CWSA 11/16/25
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pursuing a relationship, my old guy question is this. If there's anybody young enough to answer the question, do young people pursue or do they just exist? This is a serious question, by the way. I don't know the answer. Do young people pursue relationships as much as they used to? Or do they just say, "No, I'm going to do this thing. I'll probably meet some people. Some of the people I meet might…
← Previous segment →how to talk to somebody, learn how to get past embarrassment, learn how to enter a room and own it. Those are pretty valuable skills. So if you think there's no way to learn it because there's something about the world that changed, not really. There are just three books you can read: Reframe Your Brain, Win Bigly, and How to Fail at Almost Everything and Still Win Big. They will fix you.
All right, so this leads me to my most fun story of the day. How many of you know who billionaire venture capitalist Bill Ackman is? Does that name ring a bell? So I wouldn't call him a conservative or Republican but he certainly went from deep Democrat to maybe I should rethink this whole thing. I think I'd call him an independent, but I don't want to be the one who labels him.
So apparently he had a suggestion for how to meet a young woman, and this is based on his dating experience. All right. Now, here's what you need to know about Bill Ackman. If Grok is not lying to me, he's 6'3. He has perfect hair and he has almost model-like male good looks. Went to Harvard, is a billionaire. And he's going to teach you how to pick up women. And here's what he teaches you because he thinks it's about the line that you use. So not entirely that, you know, it's also the having the guts to go up to somebody. That would be at least half of it. But he says use this question. He says, I would ask quote, "May I meet you before engaging further? I almost never got a no."
All right, let's get back to the real world. How many of you live in the real world? Anybody? Most of you. Oh, most of you live in the actual reality. In your experience, how many handsome 6 foot 3 billionaires with perfect hair get turned down when they introduce themselves in a public place? Has that ever happened in the history of male and female interaction? Has that ever happened?
So I don't know if Bill Ackman is not aware of his own situation because sometimes we're not aware of ourselves, right? It's easier to see somebody else than it is to see yourself. But that's kind of funny. Now, I would go further and say that "may I meet you" might be one of the worst pickup lines I've ever heard. And indeed, the reason I saw it at all is that there was some young man who had read this advice and he tried it out at a bar. Now, he didn't tell us what he looks like, but I'm just going to guess. Probably not 6'3 with perfect hair and a billion dollars and handsome. Probably not.
Anyway, he not only got turned down when he used that line, he got mocked mercilessly and the women that were with the one he targeted for his approach, they all just laughed until they cried at him while standing right in front of him. Now, you see the problem?
All right, let me tell you what's wrong with this line. "May I meet you" will work for every 6'3 billionaire with good hair. It'll work for all of them. Why? Because the woman doesn't care what you say. If you have all that other stuff working for you and plus he's an interesting guy. I mean he has the whole package, right? So it shouldn't be any surprise that no matter what he says it works. But here's what's wrong with what he says. He's asking for permission. How many of you ladies got the ick when you heard that he asked for permission to meet you? It's not permission to go to your house. It's not permission to hug you. It's not permission to rifle through your purse. It's permission to simply say who you are and ask who the other person is. That is so ick. Am I wrong? Ladies, back me up. Back me up.
Now, but while I say it's ick and weak, wouldn't it be a lot stronger to just say, "Hi, I'm Bill Ackma
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n." How would that not work? Hi, my name's Bill. That would work every time. That would work 100 percent of the time. Anyway, so my advice is just go introduce yourself if you're that handsome. It'll all work out. Robot surgeons. We talked about that. We don't need to talk about robot surgeons anymore. Dershowitz is fun to check in with every now and then when there's a legal story. And this Eps…
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