Date Master Dan

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.

The Playboy's Playbook: Why You Need To Date With Pure Intentions, Not Cruel Intentions

ByDate Master Dan
During a heated scene in the Gen-Y classic, "Cruel Intentions," Sebastian, played by Ryan Phillippe, proclaims to Annette, "I can't win with you." In her sweetly innocent tone, Annette, played by Reese Witherspoon, wholeheartedly responds, "It's not…

The Playboy's Playbook: To Bone Or Not To Bone, That Is The Question

ByDate Master Dan
A lot of ink has been spilled on both sides of this argument. If you sleep with him too quickly, he’ll lose interest, think you’re easy and won’t have respect for you because he doesn’t think you respect yourself. If you wait too long, he’ll get…

The Playboy's Playbook: The 20 Reasons Why She’s Not Getting A Second Date

ByDate Master Dan
New York City is a special place. I’ve heard a lot of people say that it’s easy to meet people, but difficult to form meaningful relationships. I can agree with that. It’s an enormous city with millions of people and the next best thing might be…

The Playboy's Playbook: Avoiding The 'Marriage Zone' If You're A Guy And Overcoming It If You're A Girl

ByDate Master Dan
Readers of this column undoubtedly have heard the many wonderful reasons to be a healthy, gainfully employed 29-year-old single male living in New York City. My money is my money, I can go where I want, do as I want, but most importantly, my access…

The Playboy's Playbook: The Top 13 Ways To Kick Her Out Of Bed On Sunday Morning

ByDate Master Dan
The challenge isn’t getting her home; it’s getting her to leave. It’s safe to assume that most guys go out at night with the intention and desire to meet a nice girl and bring her home. Don’t, however, start high-fiving yourself and doing a victory…

The Playboy's Playbook: Why Gen-Y Weddings Have Gotten Out Of Hand

ByDate Master Dan
Welcome back to the next installment of The Playboy’s Playbook. Last week, we lightened things up a bit with The 17 Reasons Why It’s Great Being 29 and Single, I hope you all were entertained. Now that we’re clear on how enjoyable freedom and…

The Playboy's Playbook: The 17 Reasons Why It's Great Being 29 And Single

ByDate Master Dan
Even though Generation-Y has cemented the trend of marriage later in life, as a 29-year-old single guy, I still get grilled by my family and married friends as to why I don’t have a “someone special” in my life. The honest answer is that, being…

The Playboy's Playbook: Second Date Slump

ByDate Master Dan
So you had a pretty good time on your first date, congratulations.  She showed up on time, you were totally on your game navigating the conversation and got a good spot at the bar, you worked smooth transitions and a nailed the non-awkward make out…

The Playboy's Playbook: The Post-Date Hook Up

ByDate Master Dan
Well hello there. Glad to see you’re back again.  I hope you enjoyed your weekend, and maybe even incorporated some of my tips into your dating game.  As we progress further into The Playboy’s Playbook, you might start to see a pattern of how I like…

The Playboy's Playbook: The Date

ByDate 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…

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

ByDate 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…