The Playboy's Playbook: Observations From A Serial First Dater

by Date Master Dan

The dating landscape for Generation-Y is complicated for both men and women. Old school rules are called into question and replaced with detailed instructions on how to play the game, which has become harder to win than a tennis match against Rafael Nadal on clay. It’s a wonder how any of us actually connect and form meaningful relationships with our significant others.

Women complain that men are clueless when it comes to wooing a girl. Men complain that women are too difficult to decode. Wouldn’t it be great to have an experienced friend who we can defer to with all of our inquiries on dating and hooking up? Someone who knows the difference between when she’s blowing you off and when she’s playing hard to get. Or who can accurately explain his ambiguous text messages and tell us what the right move is when we’re at a late-night crossroads. What we all could use – regardless if we’re male or female – is a third party that has years of dating experience, advice to share, and can tell us like it is.

Well, we’ve finally found him. Readers, meet Dan. Dan, meet the readers. We have a feeling everyone will be fast friends with the launch of our new The Playboy's Playbook column. Dan is an expert when it comes to breaking down the dating scene, determining when it’s appropriate to text “come over” at 3 a.m., and deciding on where we should take our Tinder date if we want to get laid at the end of the evening. He’s a real 29-year-old bachelor, living in NYC with a coveted job, and ready to spill his relationship secrets to both genders. We’ll leave the rest of the introductions up to him.

Elite Daily is rolling out a revolutionary column that will finally offer a real perspective on dating. He’ll give us insight into how to behave (or not!), what to expect, and unconventional ideas to winning our partner over. We’ll be covering everything from first kisses to final breakups – and we hope that our readers will gain a little piece of mind and a lot more confidence in the dating world. It’s time to start playing the game the right way.

Up first? What goes on behind-the-scenes before the big date…

“Hey, wanna get set up?” I get it all the time. At 29, with most of my hair, a job, and a decent apartment in the upscale West Village, I’m either an eligible bachelor or a charity project for my friends’ girlfriends, fiancés, wives, and sometimes complete strangers. Am I that pathetic? Is there a stench of desperation emanating from me? Sometimes I wonder if any thought is even put into these set ups, or if it is more like, “hey, you’re single, she’s single, you never know!”

No, I usually do know, and I’d rather save the $80 and a Tuesday night, but I digress. Maybe all of us single folk should flee to a remote island to remove ourselves from the grasp of amateur matchmakers.

When presented with a potential set up, it’s the same drill every time. Give me a name and a few vitals, and I’ll check her out on Facebook to search through her pictures for the bathing suit pics (note to girls: it would make guys’ lives immensely easier to label a photo album “swimsuit” or “beach fun” rather than make us search to find what we’re looking for).

After I’ve convinced myself that she’s cute enough for a weeknight date and made sure that I don’t have anything better to do (wouldn’t finally starting "Friday Night Lights" on Netflix be a better use of my night?), I get the #, make sure this poor girl has been informed by our mutual matchmaker that there are people out there working on her behalf, wait a few days not to seem desperate, then make the call.

The Initial Contact

Sunday and Monday nights are optimal nights for the first conversation call, as she’s probably figuring out plans for the week, and Wednesday isn’t bad either to make plans for the following week. Thursday, Friday and Saturday are definite non-starters.

If I were a chump, I’d text, but I’m an adult, and not only do girls appreciate a call to set up a date, it gives me a chance to put a voice to a face and get a sense of her personality. Another note to girls -- I should really just make a list at the bottom -- nothing infuriates me more than leaving a voicemail then having you text me back the next day telling me you got my voicemail. I know you got my message, I’m the one that left it, I called you for a reason, be a grown up and call me back. I realize that text messaging has stripped you of your ability to properly communicate on the phone, and it would have been easier for me to send you a Facebook message while sitting on the toilet, but I didn’t. I’m not looking for a pen-pal, call me back.

My ‘first call’ game is pretty tight, and it’s because I stick to the basics. Men, even you can take a page from this piece. Get the vitals -- where she lives and works (comes in handy when picking the date spot), what she does, where she is from, and maybe toss in a stupid joke (only kind I have); but I generally keep it pretty short. If she gets a little chatty, which can happen from time to time, I’ll usually just tell her we should probably save some things to talk about on the first date. A good transition that I’ve found helpful is “so Lindsay/Jessica/Lauren/Carly/Jaclyn/Emily, if you’re not too busy on Tuesday/Wednesday, let’s meet up for some drinks. I try not to ask questions, just make vague statements. She’ll say “sure,” to which I’ll reply that I’ll text her the day of and we'll figure out a plan.

The Game Plan

I used to put a lot of time and thought into picking a first date spot, but now in my late 20s, I couldn't really care less. From 2007-2010, also known as my “amateur dating days,” I thought I knew what I was doing and hit the wine bar circuit really hard. I might have done a Yelp search for “Gramercy Date Spot” at least 100 times -- they should have cut me off a while ago -- and I’ve been to those lame bars on Irving Place more times than I care to admit.

I’ve spent way too much time at Merc Bar, and actually got excited when Biblioteca opened up in Murray Hill, just to have some variety for the 34th street gals. Now I cringe when I walk by that place, it’s the worst (or maybe my previous choices in lounges were the worst). Today, I really don’t give a crap about the place -- give me some setting with dim lighting, cheap drinks, a little music, and tattooed patrons, and I should be all set.

One thing I do put some thought into is location, as I try to make it somewhat convenient for her while trying to limit my cab fare to $12 each way. When I ask where she lives, I keep my fingers crossed for anywhere but the Upper East Side, as I’m almost always coming from the West Village downtown. I would always prefer a local West Village spot -- who wouldn’t want home court advantage?

But I really can only get away with that if she lives on the west side (not Upper West Side), or as far east as Union Square. If she’s a Murray Hill/NoGra (North Gramercy) or Gramercy chick, I’ll usually pick something in Gramercy or the East Village area. Upper East Side turns into a post-work date, and there are ample lame wine bars in the 50s to hit up.

There you have it. One phone call and a half-assed attempt at picking a decent spot, and we’re already 50% of the way there. Once you have these basics down, you’re practically guaranteed a second meeting. Now that we’ve got all the details squared away, it’s time to watch "The Challenge" on MTV (hey, I don’t judge you for watching "So You Think You Can Dance!") and wait for the big evening to arrive. Stay tuned for the next installation of my column, which will give the whole rundown of THE DATE.

Playboy Dan | Elite. 

Date Master Dan is a 29 year-old bachelor living in NYC with his rescue Golden Retriever, Stanley. As the eldest of three siblings (brother and sister), he knows the inner-monologues of girls and guys alike. Dan is an active guy who enjoys skiing, rock-climbing, and grilling at his infamous Beer-B-Q’s. He likes live music and good company to share in it. And above all, he’s an expert when it comes to mastering the dating scene. 

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