Approaching a complete stranger on the street is really, really tough. Approaching a woman on the street you don't know at all, especially if she's walking this way and you're walking that way and you have like three seconds, that's really, really hard.

I can just say the last thing you wanna do—we'll start there, we'll start with the thing you don't wanna do—is to try and force it. If it feels like she's on the phone, she's doing something else, and you reach out or something, that's gonna be not just creepy, that's scary. You have to read the situation; you have to let it be natural.

Just an aside in this—I was not aware of this, but apparently one of the places that women do not like being approached the most is in a parking lot. Apparently, women feel very vulnerable. Almost never do they want anyone—unless you're coming to save them from a dangerous situation—they don't want to be approached when they're in a parking lot, apparently.

So if you meet some woman at a supermarket, don't wait until she goes out to her car to approach her. For some reason, women feel very vulnerable and really not comfortable in those situations. So just a little aside: don't approach a woman in the parking lot.

But approaching her in public on the street, in the supermarket, something like that—again, if there's some kind of situation like you're in a supermarket and people are just going from point A to point B, and there's a place for a minute—that's naturally going to be a little bit easier because you have a reason for not moving, she has a reason for not moving. So it's a more natural setting.

So I would say look for the natural settings, and something where she's not going somewhere, you're not going somewhere—that's easier. If you're waiting in line somewhere, that's even more natural because you really have nothing to do, and talking to the person next to you might even be the most natural thing to do.

As far as the not being creepy part of it—which is tricky—the creepiness comes out because you're just thinking about her and you're doing something with her that you don't naturally do normally with other people. That's what creates the creepy feeling.

So if you only ever approach anyone in public when you're attracted to them, that's gonna feel creepy. If, however, you start to practice connecting with people in general—older people, younger people, men, women, couples, people that are alone, groups, individuals that are by themselves—and you just get comfortable and natural with connecting with almost anyone in the situation that you're in, you will start to feel more natural and more confident when you're doing that.

And then when you see the one woman that you really do have an interest in, you're really just talking to her the way that you've been talking to plenty of people around you throughout your life. You know, several times this week you've had conversations you just strike up with somebody in public. It's a natural thing; this is what you do.

This is what a confident man naturally does. When you are already in that role, you're already doing it, and then you see the woman in the street that you really wanna talk to, you're doing what you naturally do.

The creepy thing is doing something that's not natural. There's an agenda, there's something you want in your mind that you're going towards. That's what strikes a woman as creepy. But if you do this all the time and you're doing it with her the same way you do everyone else, she's gonna feel welcomed in. She's gonna feel a lot more safe.

So that's really the trick behind it. In the book Women Love Unicorns, there's actually a section in there that's called Magic Circles, and it's about constantly inviting people in and creating this sort of inviting, energetic, joyful place that you're in, and that you're inviting other people into constantly. They feel alive when they're in your presence.

That's exactly how you wanna be approaching a woman when you're approaching her in public. You're inviting her into this happy, celebratory, calm but joyful place that you're in. You're inviting her into your magic circle that you're also inviting plenty of other people into.

That's what I have to say about approaching a woman on the street.