This is the next installment of the book I never published regarding my history with women and the lessons I learned. If you haven’t yet, you should read parts one, two, three, four, five, six, seven, eight, nine, ten, 11, 12, 13, 14, 15 , 16, 17, and 18 before you read the article below, so you can be up to speed on where the story picks up. I’m not describing literally every woman I dated or had sex with during these times. I’m just focusing on the most noteworthy ones. Everything below is 100% true to the best of my memory, journals, and spreadsheet records, though all the names of the people described have been changed.

-By Caleb Jones

We last left off about ten years ago…

March 2010

At the start of the month Shelly had LSNFTE’d me because I didn’t want to get married and Emma floated away, which I let her do (she’s the one who had herpes so I had no desire to keep her permanently in my life). That left me with my two solid women (and my two favorites), HBM and Charlotte. I was very happy and really liked both of them. They were both wonderful, friendly, sexual, consistent, and reliable.

The problem is that my absolute minimum number of women in my life has always been three. As I had learned before, the problem with having just two women is that it’s too close to one woman, which is monogamy, and therefore unacceptable. If you have two women, the instant one of them leaves, or gets a boyfriend, or does a LSNFTE, or you have to next one of them, then boom! You’re now down to one woman. Which is monogamy. Which I don’t do because it doesn’t create long-term happiness.

Therefore, I learned that, at least for me, the minimum safe number of women in your life is three. This way if one leaves, I still have two left and have plenty of time to go replace that third one. Even to this very day, over ten years later, I have still adhered to my Rule of Three without fail. (For example, today I have Pink Firefly plus my two consistent FBs… three women.)

Lesson Thirty-Two

The ideal minimum number of women in your life is three. One is monogamy. Two is monogamy waiting to happen. Three is ideal.

So, I followed my standard Blackdragon system. First I went through my phone and looked through all the women I had sex with at least twice (Lock-In) and picked out a few I thought would be pleasant to see again. I sent out several “Hey! How’s it going?” texts to several of these women and waited to see which ones responded.

Since I had only been doing this for three years, this list of women was not very large (today it’s huge). I didn’t think that statistically there would be enough ex-FBs and ex-MLTRs to guarantee that I would pull at least one or two of them back into regular rotation.

So, I hopped back onto the dating sites, resurrected my profiles, and fired off about 200 openers across three or four different sites. I figured this plus my ex resurrection efforts would be more than enough to bring in at least one or two women. And I was right.

This particular online dating blitz yielded two first dates. One was with a 32-year-old dark-haired Russian woman and the other was with a really cute 19-year-old with extremely long brown hair (not my favorite) and a very curvy but trim body (my favorite).

Unsurprisingly, the Russian woman turned out to be a total bitch and the first date with her was an unpleasant experience. I describe what happened under “Russian Girl #1” here. This was several years before I would notice a near-consistent pattern of problems from Russian women that I never experienced with any other race or nationality of women (though I still noted what happened, as I always do, for my records).

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On the other hand, the 19-year-old, who I’ll call Courtney, turned out to be a huge victory. I did the standard Blackdragon one-hour first date, meeting up at a local Denny’s (she was 19 so she didn’t care) and just ordered soft drinks. We talked for the entire hour and we hit it off. She was extremely shy with a very quiet voice. At times I wasn’t sure if she was interested in me at all (some women are like that). Regardless, when I hit her up the next day to come over to my place, she agreed, and we were having sex within about 40 minutes of her arriving at my house.

One hour and forty minutes grand total meet-to-sex, with only $13 spent, with a very cute girl who was almost 20 years younger than me. This was standard stuff at this point.

Even better, Courtney turned out to be one of the most long-term and enjoyable relationships with a VYW I have ever had in my life. She was very smart, extremely low key (and thus low drama and low jealousy), she had the exact physical traits I like, and we were very sexually compatible. I made her a low-end MLTR and saw her for over a year, consistently. Moreover, during that entire time she never once brought up the topic of monogamy or exclusivity. This makes her a unique exception, since even the most sexually relaxed women will eventually bring this up after a few months, requiring The Talk.

While this was all happening my fishing expedition for some returning exes also worked. Of all people, crazy Selina responded to my text and was enthusiastic to hang out again. I actually hesitated to do so, judging from my numerous crazy experiences with her before, but she was a very hot 20 year-old who I wouldn’t have to redate, and I figured I already had my other solid women, so I said, “What the hell.”

Lesson Thirty-Three

If you manage the relationship correctly while you’re having it, you can almost always bring an ex-FB or ex-MLTR back into your life as long as you keep many months of radio silence after she leaves and are very patient. 

This set off a story so crazy that I have never discussed it publicly before and purposely waited until it was at least ten years old to tell it.

Selina asked if she could spend the night since she needed a place to stay for two nights. She had some kind of dispute with her mom who she was living with at the time before Selina moved into an apartment with her boyfriend (of course she had a boyfriend; Selina always had a boyfriend). I reluctantly agreed (I hadn’t yet solidified the Cardinal Rules against having FBs spend the night) figuring it would only be two nights.

I coordinated with both Selina and her mom to meet them and pick up Selina. I had met Selina’s mom two years prior when I was playing around with Selina the first time. Mom was around my age (I was 38 at the time), fit, and very attractive. (Yeah. Now you know where this is going.)

Selina came over, stayed at my place for three days, and left without incident. Then Selina’s Mom started contacting me without me contacting her first, even to the point of sending me flirty messages.

I can’t give any detail about this next part, but to summarize, Selina’s Mom apparently had a thing for me regardless (or perhaps because of?) the weirdness of me hooking up with her daughter. We eventually met up in a parking lot briefly and talked for just a bit. Two days later Selina’s Mom was over at my place and… yeah, it happened.

It was a one-time thing, which was probably for the best. Pretty damn fun though. I also didn’t see Selina again for a while since she was more focused on her boyfriend. Again, for the best.

But there would be more from those two and others in their sphere. A lot more.

Around this time, Charlotte dropped a little bomb on me. One night, while in bed with each other, she asked me if she could be my official girlfriend. It had been over eight months, so I wasn’t surprised. She assured me that I could still have sex with all the other women I wanted, and she meant it (her jealousy was almost zero, which is why she was so wonderful). She just wanted us to officially identify each other as girlfriend and boyfriend.

I still wasn’t ready for anything like this. A god damn girlfriend, OLTR or not, was the last thing I wanted. I had only been out of my divorce three years and wasn’t done being 100% free and living out all of the sexual fantasies I hadn’t experienced yet. I also did not want a girlfriend taking the focus off my primary purpose in life: my businesses, which were starting to do well again after the financially difficult year of 2009.

In retrospect, I could have just solidified her as my high-end MLTR and given her the title of “girlfriend,” but back then I wasn’t 100% sure how to combine the term “girlfriend” with an MLTR (rather than the OLTR which is what it’s meant for).

So, as sweetly and as lovingly as I could, I told her no. She cried a little bit, gave me a hug, and told me she understood. Within a few weeks she was gone. Not a LSNFTE since there wasn’t another man in the picture. She just wanted more.

It was fine though. She came back a few years later. They always do. Plus, Courtney was essentially replacing her so I was still covered, and two more women would soon return. More on that in the next installment.