The Playboy's Playbook: The Date

by Date Master Dan

Welcome back to the second installment of the Playboy's Playbook. You must have learned something interesting from the first article, “Pre-Date Set Up,” so now you're back for more, as we go from the initial contact, through the game plan and now on to the date.

Before we progress, let's recap a few key points from the first article.

Guys: Pick up the phone and call, keep it short and to the point. Get an idea of what kind of girl she is, especially if you are sarcastic and funny, you don't want her thinking you're a whack job when you tell her you're taking her out in Harlem and she should wear a comfortable pair of shoes and bring mace. If she thinks you're serious, I recommend three stiff cocktails before the date instead of two. In addition, pick a spot convenient to her apartment.

Girls: More bathing suit pics on Facebook and help us out with the labeling on the albums. Time theft at my company is real -- I can only steal a few seconds here and there and the screen is usually minimized, so help me out. When a guy calls, call him back. If you're busy when he calls, it's perfectly acceptable to text him back right then saying you saw he called, but you're busy and will call him later, but don't text back and expect him to be excited about it.

A few notes on dating in the greatest city in the world before we proceed. Dating in NYC is a mixture of excitement, disappointment, pleasure, brutality, and tomfoolery. People date for a lot of different reasons -- to meet new people, to hook up, to find a significant other, and to get married. I'm not quite sure where I fall within this spectrum, but I do suppose it changes frequently based on the season, the vacation schedules of my friends, and the general economy. It was pretty easy getting reservations back in 2009 during the recession.

I have friends who are married to the first person they dated, and other friends who are slugging it out with me on the slow track, feeling absolutely no pressure at all. Whatever your reason, I hope this next chapter of the Playboy's Playbook will give you some tips to become a better dater and reach your goals faster, whatever they might be. So enough screwing around with Facebook and G-Chat, it's now time for THE DATE!

The Text Game

I tend to wait until after 3 p.m. to initiate the convo; for some stupid reason, I like to make her wonder if we're actually going out. Before you've convinced yourself that this move makes me a player (or a total genius), I warned you that I'd be candid – this is the game and this is how I play it. To be honest, some days I'm really busy and don't get around to texting until later in the afternoon, but other times, it's certainly deliberate. Actual text of a real conversation from a few weeks prior is below (guys, notice the lack of emoticons in my texts):

Me: hey what's up? Her: Hey! Not much, just super busy at work!! What's going on with you?? Me: just working, we still on for tonight? Her: Yea! What did you have in mind? Me: Let's meet at Von Bar on Bleecker and Bowery, around 930. Her: Great! See ya then

This was a set up, and the phone call a few days earlier actually went pretty badly. She didn't say much, didn't seem all that interested in going out, but I set up a date nonetheless. She lives in the East Village, and given her lack of communication skills on the phone, I picked a spot that was dark, had a DJ and a dance floor, so we could be distracted with music and dancing (hopefully), and wouldn't have to sit there and just talk for 2 hours. How did the date go? Chlorophyll? More like Borophyll…

Anyway, the logic here, ladies and gents, is that the female wants you to make the decisions, pick the spot, call the shots, steer the conversation, pick up the check, and be a gentleman. Never ask a girl where she wants to go or what she wants to do on the date.  Don't even ask her which table she wants to sit at. If you want to step up your game, ask her what she'll be having, then order it for her.

Note to both parties here -- it says a lot about your character the way you treat and interact with people in different societal levels than your own. When you're a bitch to the waitress because she gave you a vodka tonic instead of a vodka soda, or you act like a pompous ass when the host doesn't give you the table you want, everybody notices, and it's not a good thing.  We're all out trying to have an enjoyable evening, let's try and be pleasant to everyone.

Getting There...

My move is usually to show up 3-5 minutes early, go into the bar to check out the seating situation and plan my attack. I particularly like a corner booth or some other set up where it's easy for me to sit next to my date instead of directly across from her. It increases the chances for some casual arm or leg touches, and who knows where it goes after that.

The only downside to showing up a few minutes early is that girls almost always show up 5-10 minutes late. Honestly, ladies, what's up with that? You can do better. I don't even care about the wasted time on bad dates -- you can keep it; it's all a life experience. What I want back is the 10 minutes I stand waiting outside a bar looking like a jackass playing 'Words With Friends' with my grandma on my iPhone. I know I look ridiculous, leaning against the wall, feigning coolness, and I hear you snickering as you walk by. I know it's Tuesday night and I'm outside some cheesy wine bar, guy; I'm trying to get some flow — let me be.

The Date

So now we're on the date and the only thing I can really say here is I try to keep the girl/guy talking ratio to about 75/25, meaning she should be talking 75% of the time. The catch-22 here is that she is probably not interesting, but you know what she's not interested in? Listening to you talk, champ. After the date, her roommate is going to ask how it went, and if she just spent the past 3 hours talking about herself, she'll think it went pretty well.

So just ask her some random ass questions like what her favorite animal cracker is and sit back, relax and think about your fantasy football pickups you need to make before the waiver deadline in the morning.  Also, I can't imagine that being a good listener will hurt your chances when you try and close.

Depending on how the date goes, I'll probably suggest that we relocate to another spot after a few drinks, or take a walk and see what we can find.  This tactic is called bouncing.  By going to multiple bars on one date, she'll have memories of being at numerous bars with you, which creates the impression that she's known you longer than she has, thereby increasing her comfort level.

The Check

But before we head out to another bar, it's time for that check to come, baby, and I can't wait to see her reaction. One of three things is about to happen.  She'll do the right thing and do the dance, go for her purse and offer to split, knowing very well I'll be paying anyway. Or maybe she'll sit there like a lady, smile, let me pay, then thank me for the drinks. Or, she could quite possibly be an awful person, watch me pay, and forget to say thank you.

Ladies, do the right thing: do the dance, pretend to go for your wallet to split the check, or just don't sit there like you're expecting us to pay.  We know it's ridiculous, we know we are paying, and we know that you know that we know that you know that we know, but just do it; it makes it easier for me to swallow that tab for two garbage drinks each and a crappy crostini while listening to your stupid stories about your weekend in the Hamptons with your camp friends and how you are all so over Fire Island.


Congrats on making it this far on date #1, a lot of people better than yourself have crashed and burned before getting to this point. Are you having fun yet? Do you want to blow your brains out? Slip some roofies into your drink? Hopefully both parties don't feel hoodwinked and are somewhat attracted to their date, but at this point I'm usually doing the math on how much this evening is costing me and how I could have better spent my time and money.

It's around this time that I'm thinking about where the closest Citi Bike station is to save me some cab $$ on the way home and where I can get a slice of 99 cent pizza. But before its time to say goodbye, am I going in for the makeout? Join me next week and we'll tackle head-on (literally) the make out and proper ways to get it done.

Until next time - just do the right thing,

Date Master Dan.

Top photo courtesy AMC/Mad Men