It’s Wednesday, which means its “Dear David” day. Today I’m answering a question from Mark on approaching women in public. It’s interesting, because it’s something I talk about a lot, but this takes the subject a little deeper.

Mark asks…

David, I love the idea of using observations with women. I understand pickup lines don’t work, and I get that women prefer guys who are natural and confident. Here’s my problem. Sometimes I’ll go over to talk a woman, and a random observation will pop into my head that ends up sounding weird.

As an example, I was standing next to a pretty blonde in a clothing store. She was looking at purple umbrella (they sold accessories too!) The first thing that popped into my head was, “Nice. I’m guessing you like purple then.”

She looked at me like I was a bit crazy, and said, “Kinda.”

I was going to come up with something about purple reminding me of Barney the Dinosaur from when I was a kid, but chickened out because I got the feeling she was unimpressed with my opener anyway!

So, when making observations, how do you know how to come up with something she’ll want to react to, rather than being random?


David says…

Hey Mark,

At least you’re actually out there taking action and trying to meet women. You made a good attempt at an observation, but I’d have probably gone for something like, “Wow, are we expecting rain or something? It looked pretty nice out there earlier!”

Just call her out a little bit. Be playful with her. But, look, here’s how I suggest coming up with approaches and observations which feel right, and more importantly that will get her talking.

I call it proximity approaching. What you need to do is take a good look at your “target.” What are they doing? Are they looking at an umbrella? Are they handling the fruit in a grocery store? Are they looking at the menu in a coffee shop?

Make sure you have an idea what she’s up to, and now you can come up with a non-threatening conversation, which won’t make her feel like you’re hitting on her. Once you have something in mind, go right over, and don’t wait. Come out with your opener and wait for a response, but be aware women won’t always respond. As you’ve seen, sometimes they’ll look at you weirdly and walk away. It happens. So what?

Just make sure if she responds you have some sort of comeback, or story of your own to tell her. You want to project the image of confidence, with a sense of humor. It shows you’re easy going, but it also tells her she doesn’t intimidate you, which should instantly relax her.

Once you’ve been talking for 30 seconds or so she’s yours for the closing.

Likewise, if you’re in a grocery store and you see a woman sniffing melons. I would go over, look at a melon and say, “What should a ripe melon smell like? These all smell the same to me!”

Chances are she’s going to respond to you. Now you need to be ready with your comeback or story. Say something like, “I can’t risk buying an unripe melon. When I was a kid, my Mom brought an unripe melon and it tasted disgusting. It’s scarred me for life!”

This normally gets a laugh, and if you’re really lucky she’ll ask you how old you were or something. If she does, you’re on to a winner. In short, Mark, I don’t think your opener was too much of a problem. You should have followed up with the Barney comment. I bet you’d have got a laugh and a better result.

Remember, it’s not how you open but how you close. Even the best opener in the world won’t help you if you don’t have a follow up!