V. Relationships: The Final Frontier

Girls on Rotation

What you have now is a guy’s dream: multiple women asking to spend time with you. The benefits of this situation are obvious: you get to see an assortment of naked women and enjoy different sexual encounters with each of them. However, there are certain measures to keep in place to avoid problems.

Though most women will get the sense that you’re playing the field – and most will accept this, in the beginning – none really want confirmation of their suspicions. Therefore, follow a few practical tips that will keep you out of hot water:

  • Clean the place up a bit after every session.
  • Have a drawer for jewellery; they always leave something behind.
  • Change the sheets (if using the bed) or dry clean your faux-fur rug on a frequent basis. This is as much for you as it is for her.
  • When you’re spending time together, turn your phone to silent. Even if you’re not in the middle of having sex, tons of incoming texts will arouse suspicion.
  • Don’t let her look through your phone, obviously.
  • Tell them to text first instead of “popping” by. Having girls circling your crib is bad news.
  • Have a few new, packaged toothbrushes handy for the impromptu sleepover.
  • Plenty of water. Sexual acrobatics makes people thirsty.

Also, if you find yourself in the middle of a menstruation wave, it could be helpful to buy a box of tampons or pads. I haven’t done this, but I’ve thought about it on a few occasions. I actually searched for some that my ex-girlfriend may have left behind because a girl was bleeding. No luck.

Also, if you’re having a quick session, it helps to have somewhere to be. I often have a tutoring appointment or need a cup of coffee. This gives you a good excuse to get out of your place, walk them a block and then see them off. If you have a heavy load of women, knowing how to extricate yourself becomes crucial. Don’t feel you have to give them too much information; these are casual encounters and the women aren’t entitled to a microscope on your schedule. That’s the province of a girlfriend who’s earned the right to keep tabs on you.

Managing Expectations

Most girls that sleep with you will want more. Some will be content with a booty-call arrangement and others will never return. The ones that understand the situation for what it is – a physical connection between two people – are the best. The ones that expect more need to be informed that you’re not looking for a girlfriend. Some may tenaciously cling to the idea that they’ll get you to commit. Maybe you will. Maybe you won’t.

I rarely have this problem because I must broadcast a “player” vibe. I meet the girls, we’ll have a fun night or two or three and then things will moderate. We’ll probably have a light text relationship over the next couple of weeks. My moderate interest probably indicates that I’m not suitable boyfriend material. Actually, what often happens is that the girl gets very horny and texts a lot after our first session or two. I’m usually satisfied with her at that point and I’m looking at the next girl. It’s a funny reversal of roles. I try to be as nice and accommodating as possible.

My goal when I’m single is to have as much fun with as many different girls as possible. I love a lot about women – how they look, feel, smell, laugh, giggle, their curiosity, etc. – and I want to have an abundance of them in my life. I don’t want to hurt feelings – that’s the last thing I intend to do. Unfortunately, it’s hard to have many women in my life without occasionally disappointing some expectations. I mitigate this by being as up-front as possible. Obviously, I can’t say, “This is about sex and nothing more. After two weeks’ time we won’t see each other again.” Few unpaid women would be up for that. It’s also not accurate, because some stay in my life on a continuing basis and occasionally I forsake others for the love of a single girlfriend. But, I do try to discourage a girl’s imagination by avoiding romantic moments or situations in which she can envision me as “her man.”

In this regard, paying for a woman takes on a particular significance. Most women can’t help but view you as a “provider” when you pay for them. Taking her out and leading the night casts yourself as the dominant, decisive male and that role encourages her to imagine you as a boyfriend. If that happens, you’ll have an emotionally invested woman on your hands and the situation becomes loaded. You’re no longer having casual sex.
So, within reason, keep the relationship to the bedroom if you intend to maintain something casual. Going out to a meal after sex is fine, but lots of outings or fancy events where you’re not being sexual sends the wrong message and can easily confuse you or her. A player in Los Angeles once commented that if you see a girl more than twice a week, she’s your girlfriend. There’s truth to that.


Given the chaotic nature of New York City, planning a date more than two days away is foolish. In fact, things turn out best if they occur that evening because you keep the momentum of the first meeting. The best nights of the week to meet are Monday, Tuesday and Wednesday. The other nights can work well, but often the girl has other plans or she expects a real “date.” That’s not to say you need to take her on one, just that she’ll be thinking about being taken out; her objections may be more vociferous. I’ve already discussed the methods of double- and triple-booking. Just make sure you have the energy to manage all those women and the willingness to lose a few if you hit snafus. Like I said, if you stand her up, chances are she’s gone forever.

The way I work a typical week is to get text confirmations from the girls a few days prior. Then, the day-of, I will send a short text like, “See you tonight.” They’ll come back with “when/where” or some request for particulars. I usually have them arrive at 9:30 or so. This gives us time to chat before getting jiggy. If you have a calendar, or Outlook, you can line them up all week long. If you have a date every night of the week, you’re sure to be getting laid.


How do you narrow it down to your core customers? Well, some girls won’t play and they can be nixed. Others will play and disappear, which is frustrating, but this is casual dating so it cuts both ways. Your steadies will get the picture, soon enough. This may be the first time in your life when you’re done having sex with a good-looking girl and you go to the bathroom to piss and check your phone and two other cuties have texted you, “Can I see you tonight?” Work through the system in this book and your dating reality will be totally transformed, I guarantee it.

A benefit of having ample inventory is that you can now make choices: tattoos, or none?, smoker or not?, tall or short?, breasts or ass? Finally, you’re in a position of strength. Don’t be too quick to give it away. Remember, that once you’ve entered a relationship with a woman where strong feelings are involved, your options will decrease to zero. In a monogamous relationship she is in control because if you stray, you’re in the wrong and women generally don’t have the same sexual urges to go outside the relationship. So, be careful about forfeiting your abundance, should you chose to do so.

Breaking It Off

Like a band-aid, I’d say. One of the benefits of being a strong male is that you can be sensitive to a woman’s feelings but still direct. I’ve told a number of women it’s over, or that the attraction wasn’t there. They are hurt a bit, but we’re both better off for it. The tangled, struggling separation that some guys create is painful to watch. If you’re done fucking her, let her know it’s over and that you had fun.

I’ve found that sometimes it’s nice to keep them on the back-burner if they live out of town, for instance. It’s nice to have a fresh piece of booty when she flies in for work every six months. Often times, it’s not necessary to have a “hard-line” talk about the relationship. If she’s a hottie and your attention falls away after an initial heated week, she’ll be surprised, but she’ll get the picture. Female pride works in the other direction, too and it can benefit the player. Once you tire of a girl, she’ll generally leave you alone because her pride won’t let her pester you too much. That’s generally true, especially with good-looking girls. Scrappier chicks may hang on a bit longer because they have finally got some good attention.

The Girlfriend

So, how does that one, special girl make it all the way to your heart? I won’t pretend to know what makes a girl special to each guy. Also, this isn’t a relationship guide, per se. If you are in a relationship, it would behoove you to maintain your male identity and individuality so that your girl maintains respect and sexual attraction. That’s as much as I’ll say about couples’ dynamics.

For me, I play with a lot of women until one – like Annie, my last girlfriend of 2 years – is the right combination of beauty, warmth, humor, compassion and courtesy. It helps if she’s a dirty little girl in the bedroom. We lived together here in NYC, which is unusual, and made a successful go of it for over two years – lots of laughs, meals, movies, sex, sleeping in, etc. I remember reading a book called Mating in Captivity when I felt the passion was seeping out of our relationship. I still see her and love her, but right now, I enjoy playing the field. Too much excitement out there!

A final note on relationships: unlike game, where you can manage to land a woman “out of your league” by developing very strong skills, long-term relationships usually require that both man and woman are on the same level. By that, I mean you can only keep up appearances for so long. A woman who wants money will get it, and if you don’t have it she will leave you. If she’s very smart and you don’t stimulate her, forget it. Also, if she’s a goddess, she’s going to have a horde of men chasing her every day, so you will have to fight the fight on a daily basis.

Just something to consider…

The Danger of Obsession

All of us are, more-or-less, prone to obsessive thoughts. When it comes to the object of our desire, the obsession can intensify. I can be as neurotic as the next guy, and on a number of occasions my thinking became unhealthy and obsessive and I felt out of control. If you choose to play the field and date a lot of women, you have to learn how to maintain a detached interest in the girls and monitor your own thinking so it doesn’t get destructive.

There have been two girls in my five years here in NYC who have triggered an unhealthy response in my thinking. I will discuss them both and describe what I did. I will also talk about general tactics that you must employ if you are to remain sane and have fun throughout this journey.

Obsession – despite the Calvin Klein fragrance – is a dangerous state of mind. There are plenty of headlines describing the murder-suicide of a frustrated lover or jealous ex-boyfriend. Part of the game men and women play is to mislead, deceive, and tempt, and it can be exciting and fun. But, sometimes one person thinks that more is at stake and really gets invested in the idea of the other person. If the feelings and intentions aren’t reciprocated, confusion and anger can follow.

The first woman, Rory, was a cocktail waitress at a very hip NYC nightclub. Through a set of circumstances, she initiated conversation and gave me her number. She was hanging on my arm the whole night, even as her boss yelled at her to get back to work. I was a bit confused by her forwardness given that she was an attractive “bottle girl” at a fancy nightclub. She explained things later, saying that when I refused her offer of a drink and did so firmly a second time, it really turned her on. Nothing seems to turn on a hot girl more than being told she can’t do something or someone. So she set up this dynamic that was both unusual and flattering for me.

We got together for coffee downtown – this was in 2004 before I had a codified system – and she made some allusions to sex and mentioned my “cock” in a graphic manner, comments that seemed incongruous with her outward appearance. Later, we had dinner and she described growing up on Long Island to a domineering father and hinted at some other family trouble. We went back to her place and fooled around.

And here’s where the seeds of the obsessive thinking were sown. Despite being quite sexual and teasing me with some touching and sucking, she kept at bay. And then, abruptly she forced me out of her apartment. I was befuddled. We met a couple of days later and she claimed that I was too intense, so she couldn’t see me. That’s when my determination to get in her pants really kicked-in. I visited her apartment at least twice unannounced and called her too many times without encouragement. A male friend helped me delete her number from my phone.

Here are a couple of things that I’ve learned (confirmed with girl #2, a few years later) these types have in common:

  • A history of filing restraining orders against past boyfriends.
  • The female initiates or makes the beginning very agreeable and easy, though doesn’t give the sex up. There’s a strong promise of sex.
  • As soon as I showed interest, she withdrew acutely, despite the fact that she had started the engagement.

My experience with the second girl, Sylvia, was more recent, but she also caused me to get in a doozy. I had more experience and I was able to get the dynamic down on paper, in black and white, so I could see that she was participating in an unhealthy push-and-pull. I met her at Whole Foods, she came over to my place that night to watch a movie, and we had a nice physical (though not sexual) time lying bed. She shared a good deal about her life, and even revealed that her sister was a former pornstar. She also had boyfriends with restraining orders, and she also behaved in a weird manner, emotionally. She was very available up front, and then when my interest was clear, she withdrew and became hard to reach. We went back and forth for a week over text and phone, with her claiming she wanted to meet. Saturday came and she agreed to meet, but her attitude was half-hearted. I gave her an ultimatum, knowing she wouldn’t accept (but hoping she would) and then got in the shower. She responded that she wouldn’t be treated that way and, “Have a good life.” I deleted her number and de-listed her on facebook. The obsessive thoughts were somewhat periodic and I actually looked her number up when my phone bill came. I explained in a text my feelings and how I had acted immaturely by giving her an ultimatum; I had felt vulnerable by showing her I liked her, and I had become too available. She wrote back that it was unfortunate, but that she didn’t want to see me. A week later, I deleted her number again, and left it at that.

There’s a lot to learn here. The situations were so similar that I can offer some general lessons:

  • Though they were both attractive, neither girl was hotter than most of the girls with whom I have sex. Attractiveness doesn’t have a direct bearing on obsession.
  • I didn’t have sex with either girl. Part of what drives the obsession is the desire and promise of sex. After I’ve had sex with a woman, a good deal of her leverage is neutralized.
  • The only way to neutralize obsessive thinking is to remove means of contact. I had to delete phone numbers and other contact information. Time will lessen the intensity of the pull, provided there’s no further contact.

I’m no psychologist, so I’m just taking a stab at this, but it seems the issue at play in these scenarios is the power dynamic between two people. Clearly, love and true affection were absent from these interactions; nevertheless, there was strong attraction. I felt as though I was drawn into an attractive scenario and then I lost control of my goal (the woman) and I lost control of myself. To regain a sense of stability, I had to cut all ties with the dynamic. Even minimal contact has to be avoided. It’s like smoking: I can’t have just one cigarette.

Maybe I’m the type of person who has a tendency towards obsessive thinking and therefore I’m susceptible to these types of traps. But, I doubt it. I think there are many situations in which an untrained mind can fall victim to obsession. The important thing is to know how to extricate yourself from the dynamic before any real damage is done. Clearly, earlier boyfriends of both girls were unable to do so on their own. Law enforcement was necessary.

I’ve illuminated two extreme examples to demonstrate the possible power dynamics that feed into obsession. Most of my “problem girls” are caught in the pre-obsessive phase and I know how to deal with them. Dealing with a potential problem girl in the beginning will save you a lot of heartache and stress down the line. They all share this common behavior:

  • You have had initial physical and possible sexual contact with the girl but it was interrupted. She remains in contact with you, seemingly interested in connecting, but she never commits to a rendezvous and you never see her.

If a girl in your inventory is doing this, you can set a final deadline (an ultimatum) in nice language, and if she fails to show, you must delete her number. This type of girl will drain your mojo and get you frustrated. Because she has let you be physical once, you have in your mind a concrete sense and expectation of being physical with her again. Somehow, she knows this. This activated desire will make you a weak hunter because you will lack discipline. It turns out that it’s much easier to be disciplined if we never have a slice of cake, a drag of a cigarette, or a hit of a drug. If you taste the honey, though, and you don’t have ready access to more, you will lose your strength. It’s happened to me.

I was recently shot down by a very hot girl in a shoe store around the corner. She was a smoking hot “10” who claimed to have a boyfriend and was sassy in response to my masculine energy. But, I walked away and haven’t thought of her again. Whatever, another hot girl. But, if I’d had a moment with her in a stairwell, or on a park bench, it would be much harder to walk away. I’d nurse that possibility until it was debilitating.

So, beware of the ones who’ve played a bit and now keep their distance. It’s unlikely they’ll present again. If they were serious about seeing you, wouldn’t they have done so already?

I cull my phonebook every month. Winnowing down the mess of numbers to those that are true responders will help keep your sanity. Don’t dedicate mindspace to those bullshit girls who are wasting your time; for all you know, they’re laughing with their girlfriends every time you send a text. Be smart and systematic about your inventory so you spend your free time on real prospects.

You’ll also know the true value of deleted numbers because few, if any, girls will text you of their own volition. Rarely do I get a text initiation from a girl I’ve deleted because she was uncooperative. It becomes clear over time that I was working a one-way relationship with some of these girls. Learn that soon, and move on. Next!