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

by Date 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 all about winning, Sebastian." This docile dispute was a powerful exchange between the onscreen, and previously offscreen, lovers.

Annette was likely the one and only girl to get through to Sebastian and put his handsome and manipulative teenager self in his place. But the two lovebirds were really ahead of their time. Annette is absolutely right; it’s not all about winning.

All of us could benefit from taking a page from her book as to how to become better romantic partners, and more importantly, better people.

Try something different for a change: Don’t win the date. It’s a novel thought, and maybe not one suited for The Playboy’s Playbook, but let’s give it a shot. If you’re not finding success in the dating world, maybe it’s time to throw out the playbook.

After all, you should never change a winning game, but always change a losing game.

Yes, this is the Playboy’s Playbook, and we’re supposed to be breaking down the dating game, but is it really a game? No. People lose in games.

I don’t know about you, but every sport I’ve ever played always results in one party winning and another party losing. I don’t think I want to be in the business of winning at another person's expense.

Let’s turn dating into a win-win situation.

Here is a crazy idea: Learn the fundamentals to forget the fundamentals. Ingrained in your nature should be the urge to take charge, do the right thing, compliment, and lift people up, but this should all be done for the right reasons. Don’t fulfill your interpersonal and moral duties to impress; do it to be a better person.

Once you've done this, you’ll elude a radiance that will attract the right person for you.

You want to make people feel good, bottom line. People don’t remember what you say; they remember how you made them feel. By doing this, you'll garner the ability to act naturally and in a genuine manner. Only then will you have something that will truly be attractive to the right individual: originality.

Your date is not your adversary. The mission should not be to outsmart and maneuver him or her with your games in order to achieve your goal -- whether that’s to get him or her into bed, or to just get him or her to like you.

I’m not advocating becoming a pushover and out of character, nor am I exercising some sort of retraction of any previously posted opinions I've discussed.

What I am suggesting, however, is to not wait on responding to him or her text message for hours in an effort to seem less eager or less interested. If you are thinking of someone, if you are genuinely into someone, communicate with that person at free will.

Call me a romantic, but maybe that one person you are dying to talk to is going crazy over waiting to hear from you. Be who you are in the realm of dating -- don’t order scotch neat because you think that’s the kind of guy a girl wants, unless you’re like me and you really do love scotch.

In the world of dating for Generation-Y, the perception resides that dating opportunities are endless. Combining the Internet and smartphones, we can literally peruse hundreds of potential dates at a time, especially with apps like Tinder. The right person could be just another right swipe away.

But in a tech savvy society, we forget that people are more than dating profiles that display five photos of them on vacation, with their dog, and doing something adventurous.

People aren't defined by still emotion; people aren't defined by stop motion to capture a moment. Perhaps our generation is doomed by the effects of advancing technology on relationships.

With such invasive access to the lives of a limitless supply of people, we have lost sight of the emotional and psychological factors associated with dating and forming relationships.

The person sitting across from you is a real person: someone’s daughter, brother, sister, best friend. Displaying a bit more compassion and empathy for people's needs, regardless of the outcome, will undoubtedly do wonders for your dating karma.

Take each date for what it is -- a chance to meet a new person and have a good time. Who knows, maybe you’ll even learn something about yourself in the process.

Until next time, opt for pure intentions…

Top Photo Courtesy: Tumblr