At The Art of Charm, we hear one dating problem a lot: “Jordan,” people tell me, “I can get the date. I don’t need you to tell me how. What I can’t do is get the second date.”

The problem? They’re failing to connect with a woman.

Remember that conversation is a team sport. You need to show interest in a woman beyond the size of her bra and how you’re going to get her out of it.

Women have it easy, in some ways, when it comes to meeting men. It’s a buyer’s market for them. All they have to do is look halfway decent and we’re all over them. At the same time, this creates pressure to filter out the bad guys and find the good guys.

How do they do this? Mostly, they look for guys with whom they have some kind of meaningful connection. While you can’t ever force that connection, you can greatly improve your odds of making it happen with the women you like. It involves two key steps.

1. Banter is light, playful and essentially content-free. This is the flirty, jokey part of interacting with a woman on a date.

2. Rapport is the more serious, non-ironic form of communication. You don’t have to get super heavy here, but you do want to keep it real.

Banter always comes first. Why? When you’re out with a new person, it’s not easy to volunteer info about oneself. Seemingly innocuous questions like “have you ever been here before?” and “do you like the food here?” can actually make a woman feel uncomfortable and defensive.

We break those walls down with banter. Gentle ribbing puts her in a lighthearted mood. Just make sure to be playful rather than mean. That signals it’s OK to relax, cut loose a bit and have a good time. You know that “sense of humor” thing that women say they love so much? Banter is the place to show it off.

Rapport, on the other hand, is where you really make the connection. Don’t worry: we’re not suggesting you give a blow-by-blow of watching your auntie die of cancer. But rapport is honest and straightforward, and it shows that you’re committed to the interaction. It even makes you appear a little vulnerable, which is like catnip to women. Think of the early montage in Wedding Crashers.

French Foreign Legion. Gets ’em every time…

This is the stage where you start forming a real bond. The content of the conversation might not be terribly exotic: jobs, cars, music, movies, favorite foods… whatever. The point is that you’re sharing something about yourself and, in turn, being allowed a little peek into the life of your date. You’re finding out real information about each other, and the commonalities draw you together.

Remember, though, that conversation is a team sport. You want to ask as much (or more) of your date as you’re giving. Women hate hearing guys go on and on about themselves. You need to show interest in her beyond the size of her bra and how you’re going to get her out of it. Trust me, most women see right through all of that.

A lot of guys make the mistake of thinking they need to go out of their way to impress a woman. But often that’s just about the worst thing you can do, as it reeks of desperation. Instead, you want to just be your “best self,” and create an environment where your date feels comfortable sharing things about herself. Then you can use that environment to create a connection based on similar experiences and feelings.

Simply do that and—trust me—she’ll want to come back for seconds.

Jordan Harbinger is a Wall Street lawyer turned Social Dynamics expert and coach. He is the owner and co-founder of The Art of Charm, a dating and relationships coaching company. If you dig this and want to learn more from Jordan and The Art of Charm team, visit You can also interact with Jordan on Facebook.