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

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 bored and still lose interest thinking you're prude. Basically, you are screwed. Winter is coming, better recharge your batteries…

Every situation is different, but I've never been able to understand how having good sex with someone will make me less likely to see her again in the future. If you want to guarantee that, I'll cancel all my dates for the rest of the week and maybe even delete Tinder from my phone. Take me back to your apartment and show me some moves you learned during your semester abroad in Barcelona.

Want to know what will guarantee that I never want to see a girl again? Three dates, hundreds of hard earned smackaroos spent on crappy wine and overpriced tapas, and I don't even get to drop a load in her presence. And when I “suddenly” don't feel like being her text messaging pen pal anymore, she has the gall to ask what went wrong…

Over the years, I have found myself trapped into a vicious cycle. I get set up on a date, we go out, have a pretty decent time, I have a mild sexual attraction to her and am left wondering what she looks like sans clothes. Possibilities are endless. She could be a closet freak with some crazy fetish, or maybe she knows some tricks that I've never seen before. I'm intrigued!

So I get a make out, and get laughed at if I suggest we have a glass of wine at my apartment. “Oh, you just bought a nice bottle of Sauvignon Blanc that you'd like to try? Come on, I've heard that before.” To which I reply, “Hey, can't blame me for trying…”

Enter date two and we've lost some of that chemistry as I get to know her better. I'm getting bored and suddenly less curious about her sexual inclinations. I do find myself on her couch at the end of the night, but it's mostly heavy petting. Sweet.

Since I like to give things a shot and kind of think it's cute that she's into me, and know that I probably just need to buy her a meal in order to sleep with her, I take her out again, put on a great show, and get her into bed. And here is the crux of the problem. It's at this point that I have the green light to take her to bone zone, but I'm already over it. She's annoying, uninteresting, has bad style, and her one-bedroom converted apartment in Murray Hill doesn't exactly scream “originality.”

But since I'm not one to turn down sex, especially after I've “earned” it, I get to business in the hope that the experience will bring me closer to this person and help develop the relationship further.

However romantic this sounds, it usually doesn't happen like that, I end up leaving 20 minutes later (big no-no), and slowly stop texting and solidify my position in her assh*le realm, never to be spoken about kindly, ever again.

So what's the deal? What's the winning strategy? Would I have liked her more had we slept together on the first date? Who knows, but at least my DPL (dollar per lay) would have been a lot lower. Too much dating, not enough boning.

Until next time, don't make him wait.

Top Photo Credit: We Heart It

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Date Master Dan

Contributor

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 skii ...
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 skii ...

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