02/13/2014 10:55 am ET Updated Apr 15, 2014

The Most Important Event on a First Date

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So the First Date is almost done. The conversation has been effortless and insightful. Your jokes were hilarious and at one point, your hands touched. And it was not awkward. The second date is looking promising. Now the waiter, who has been eyeing your lady a bit too conspicuously, brings the check. And here, dear reader, is where the most important event on a First Date happens. The one event that tells you exactly what your lady is all about: The Reach.

Before we get to that, let's talk about how you got this first date. There you were, checking your ex-girlfriends Facebook for the umpteenth time, discovering a painful, but obvious truth: 1. She does not think about you at all and 2. Her boyfriend is much cooler than you. I also know you hate Valentine's Day because its not a real holiday and its supposed to be about love, when really its about buying chocolates that will be thrown out, flowers that will wilt and die and getting a diamond that is probably a blood diamond. It looks like you might be spending the night watching When Harry Met Sally. Again. With ice cream.

But screw that! You want in on the fun as well. So you meet a girl. She's funny, intelligent, cute, etc. So you decide to have the first date. You are nervous. I can tell. You are nervous because in NYC there is so much to do and you don't know where or what they are and honestly, you can't afford it anyway. So try not to have a scavenger hunt in the middle of winter. And don't go to a movie. That's something you do together, but not really. Between the Martin Scorcese looking ass behind you and the guy farting in front of you, its not a good look. No, what you need is the classic. The dinner.

Yeah, the dinner. You wanna take her somewhere nice and affordable, with food that won't have you on the toilet seat for the rest of the night. Italian (not Olive Garden) or American (not McDonald's) are good choices. Take her to a spot you know relatively well, so you can look real cool, even if you're not.

Now the food is here. You're worrying about the food. And the drinks. Stop that. She's a grown up. She knows how to order and you don't have to do everything for her. What is important is that during the dinner, the dialogue must happen. Remember that word. Di-a- logue. Meaning two people talk. You know those guys who say, "just let the woman talk and agree with everything they say." We call those guys divorced bachelors. She is not a child. Be an active listener. Respond. Believe it or not, she does want to know more about you. That's the whole point of the first date. For you all to get know each other.

But all of this really is small compared to what is about to happen next. This next movement, or lack of one, is paramount on the first date. 8 out of 10 times, this is a great signifier of whether your relationship is going to be good or terrible. You have to wait for The Reach.

The Reach is when on the first date, the bill comes and it is time for payment your lady proceeds to reach for her purse, rummage in her bag or at least attempts to look at the bill. If she does that, you got yourself a winner. If she doesn't do The Reach? Run. Throw down the money and jump for the nearest subway. Theres is a big difference between chivalry and dependency.

The Reach says that she is perfectly capable of paying the bill, and doesn't need you to do that. The Reach shows her independence, strength and consideration. If you are a young 20 something in NYC, chances are you don't have a complete grasp on your finances. Reach women know this and that simple act explicates that. The girl who when the bill comes, is all of a sudden very fascinated by something on the ceiling, or has a bathroom emergency that is suddenly over once the money comes out, will expect you to pay for a lot more after. These are the girls that want a man to take care of her, instead of y'all taking care of each other. Lastly, the Reach lady will let you pay not because of some arbitrary and archaic tradition, or because she is a woman and you are a man, but because you want to. Hey, she did you a favor by coming out with you. The least you can do is pick up the check!

Sadly, it is now time to say goodbye. She did The Reach, so you got yourself a keeper. You have done what you can. Now its up to her. And she will text you back eventually, just be patient. You made it through the first date. It doesn't get easier necessarily, but I have a feeling it will get better. I think your Valentine's Day will be fabulous. Don't worry about how I know this, just be glad I'm not Steve Harvey. And what am I gonna be doing, on Valentine's Day, you ask? I'm not sure. I think When Harry Met Sally will be on. With ice cream.