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Here is how direct openers work. All of the literature on social dynamics tells us that the fact that you’re attracted to someone does nothing to make them attracted to you. In fact, the opposite is true. If we are too attracted to them, they will be less attracted to us. However, when you’re bold enough to tell a woman that you are attracted to her, what you’re really doing is asking for an almost immediate judgement on her part. Subjecting yourself to judgement requires balls for which you get some points.

Unless you’re good looking or bring some other kind of value – eg you’re the main speaker at a conference or you just walked into a restaurant with two beautiful women by your side – you don’t usually get enough points to seal the deal, but you do get some. The problem, as stated above, is that while you are getting some points, you are also losing some: if she thinks you’re sold on her but she’s not sold on you, you’re going to be perceived as less valuable. This is why when the best guys go direct, they almost immediately start working to reverse the power dynamic so they can establish that they are not completely sold.

For older guys, this is hard to do. When a much older man goes direct with a much younger woman, it is hard to plausibly make the case that he is not already sold on her. Why? Because both parties know that a 40 year old man might prefer a 20 year old woman to a 35 year old woman for one reason and one reason only, her looks. She’s not more interesting or more accomplished than 35 year olds, but she’s usually hotter. He already knows all about her looks so if she believes that’s what he mostly cares about, her assumption that he is already sold is going to be hard to change. Even if you’re not already sold, she’s going to assume you are.

This is why I advise most older men not to go direct. You can’t really hide attraction. Your body will give you away. But with indirect, you can more easily control the frame by showing that your attraction is tempered by a high degree of skepticism that the woman standing in front of you is really good enough for your attention.

This is how to understand this: there are probably some strippers that I might think are super hot, but I seriously doubt I would ever want to go on a date with one. This is the dividing line between pure physical attraction and real interest. When a woman meets a man with the right combination of physical attraction and skepticism, she intuitively understands that she is dealing with a high value man. Such men have high standards, and women find that extremely attractive.

If you’re going to do street stops and you’re not going direct, you’re going to need a reason to stop her, and directions are a pretty good reason. The problem with directions is that when you do try to transition to a more personal conversation, you often get that “oh now I know why you asked me for directions” look. In other words, they realize not only that you didn’t stop them for the purpose of asking directions but also that you didn’t have the balls to tell them the truth. So you get neither the points you’d get in a direct approach nor the frame control you’d get with an indirect approach.

So what’s the solution? In my opinion, the solution is to make the transition more natural. Here is how I think it should go:

1) Ask for complicated directions, directions they can’t just blurt out as they move on. “Hey, quick question. How would I get to the castle in Central Park?” That’s a place in New York that’s kinda tricky to get to.

2) If they take the time to give you those complicated directions, or at least discuss the problem with you, you can say: “Thank you. That was very nice of you. This is a pretty friendly city. Do you agree?”

3) At this point, if they’re open to chatting, they’re going to say yes or no. It really doesn’t matter. If they comment at all, you can tell them a little story. “You know, I have this friend who’s really interested in understanding people. When he’s out and about and sees someone eating, he’ll walk up to them and say ‘Hey, can I have the last bite of that?’ You know what’s amazing? Almost no one says ‘No’. He says he can count on one hand the number of angry reactions he’s gotten over the years.” (By the way, that friend is me. I love doing that!)

4) When you tell that story, they usually laugh or want to know if your friend really takes the last bite, or whatever. Let them chime in before you move on and say “Anyway, you look like you might be the kind of person who might give away your last bite.” Look her up and down and say “What do you do, sister? Do you sing, do you dance, do you read, do you write?”

Why do I think this works better than a cold read or a compliment? It’s a smoother transition from what you asked for to what you wanted. It goes ‘directions’ to ‘thank you’ to ‘that’s very nice of you’ to ‘this is a nice city’ to ‘funny story about friend’ to something more personal. And it does it without that “oh you’ve been deceiving me all along” moment.