-By Caleb Jones

This is the fifth installment of the book that I never published, regarding my history with women and the lessons I learned from it. If you haven’t yet, you should read parts one, two, three, and four before you read the article below, so you can be up to speed on where the story picks up. Everything below is all 100% true to the best of my memory, though all the names of the people described have been changed.

We last left off in mid-2007. I was freshly divorced and excited to finally be free, but was struggling to understand women and stumbling around trying to get good at dating them…

Summer, 2007

As if Melody wasn’t enough to introduce me to the world of illogical gold-diggers, I was soon onto an even harsher one. The very next woman I met after Melody was Tina, one of the most extreme gold-diggers I have ever encountered, and my very first time going out on a date with a perfect 10.

We met on Match.com. She was 25 years old and looked just like Barbie. Beautiful face, long, platinum blonde hair, fitness instructor-quality body, big-but-not-too-big, teardrop-shaped fake breasts, unusual but attractive grey eyes. She was dressed in skin-tight Bebe clothing, had a Prada bag on her arm, and drove a Mercedes that had built in GPS, which back in 2007 was unusual and expensive.

Just by the above description, some of you more experienced guys can already tell where this is going.

I had never seen a perfect 10 this up close before in real life. When she first sat down across from me, I had to fight back a visceral, physical reaction to what I saw. Even better, as she started to speak, it was very clear she was smart, highly educated, and had a high income; she was a regional manager for a national woman’s clothing store. Still very inexperienced with women after my recent divorce, to say I was impressed and excited was an understatement.

Our first date was great and we hit it off. I had to fight hard to maintain my confident, don’t-give-a-shit demeanor that I knew was critical, particularly for attractive women like this. I couldn’t believe my luck that such a woman was sitting across from me, and liking me. Yet, it wasn’t luck; it was a result of me putting in the numbers, opening tons of women online, and going on lots of first dates. Practice makes perfect, and he who puts in the most numbers wins.

I honestly don’t remember much detail from the first date (it was ten years ago!), only that we talked and got along very well. She had moved up to Portland from Salt Lake City, where she divorced her very religious husband because he was cheating on her with his receptionist (ah, monogamy).

Unlike most states these days, Utah was not a “no fault” divorce state, so she hired a private investigator to follow her husband, got a bunch of incriminating photos, presented them in divorce court, and got a huge pile of money from the deluded, Disney bastard (who did not sign a prenup of course) when the dust had settled. She then moved to Portland to start a new life.

When texting a day or two later to hit her up for a second date, I was very surprised that she said yes. Just like with Alex, ten years of monogamous marriage had brainwashed me into thinking I wasn’t attractive to women, though slowly but surely I was “remembering” that some women actually liked me, even very attractive ones.

The second date was at a seafood restaurant where we ate lunch. Going out on a lunch date is a horrible mistake with a woman you haven’t had sex with at least twice, but I didn’t know this yet.

This time, she was more relaxed and comfortable with me. After about 30 minutes of talking, it all came out. Here are a few things she said.

“I’m an expensive gal. Men need to understand that.”

“I don’t do prenups!” (stated with an angry snort)

“The women who spend $2000 a year at Bebe and think they’re spending a lot of money! Pssh! Try $15,000, Sweetie.”

“Coach bags? Um, no. Please. Gross. I only wear Prada.”

“My last boyfriend gave me a birthday present and it was only $300. Ugh! How rude. He had a seven car garage, and he can only spend $300? Yeah, right.”

I stood there utterly fascinated as these insane things tumbled out of her mouth. I had never seen anything like it (though I would again, many times). Melody had been a stealthy gold-digger, and denied what she was. Tina, on the other hand, proudly flaunted gold-digger status like it was something she was proud of, a badge of honor for all to see.

Frankly, I found it reasonably logical once I thought about it. She could get any man she wanted, including beta multimillionaires much older than her (and she had, many times). She was open and honest about who and what she was. Hey, why not? If I was a 25 year-old female 10, I’d probably do something similar.

Under normal conditions, I would have moved on. But she was so…hot! I thought I had the skill to actually have sex with her over a prolonged period of time without spending too much money on her. (I was wrong; I did not yet have this skill, though I would acquire it later.)
Yet, it was not to be. At the end of our second date, we made out in the parking lot, the heavens parted and the doves sang, and I never saw her again. She hooked up with another guy and soon transferred to a far away city. Oh well; I had dodged a bullet. I’m not sure what would have happened if we had actually hooked up, but it would not have ended well.

Jenae

Around this same time, I was still working with the client company where I met Marci (who had been fired from there). Her replacement was Jenae, a very fit 40 year-old who looked just like a younger Susan Sarandon, but without the bug eyes. She exercised often and was very trim and fit. One day at work, Jenae and I talked in her office, the very same office that used to belong to Marci where she and I used to flirt. It was one of those talks where she didn’t want me to leave… she just wanted me to keep talking to her. Always a good sign. I got her to meet up with me at a local park to “talk” some more.

I have a hard and fast rule that I have followed all of my life, and that is to never have sex with anyone I work with. In Jenae’s case, she was very dissatisfied with her job, was job hunting, and planned to quit regardless of what happened within 30 days. I figured by the time she and I actually had sex (since I was averaging three or four dates before sex occurred back then), she would have quit the job by then, thereby not violating my “work together” rule.

Almost every time I see two people who work together date, it leads to workplace drama. During the relationship, but more importantly after the relationship when there’s a big breakup, all that drama and bullshit goes right into the workplace to screw up your work (and those of your co-workers). It might be fun to work with someone you’re fucking while everything is great between the two of you, but that’s temporary. After there’s a breakup and she now hates you, you still have to work with her. People don’t understand that.

Lesson Number Eight

Never date or have sex with people you work with, period.

What you can do is get her phone number, contact info, Facebook info, or whatever, then when you or her leave the job, hit her up. That’s exactly how I hooked up with Athena and Marci. In both cases, I met them at work, but the sexual/dating relationship didn’t start until after we were no longer working together.

Talking to Jenae at the park that day, I learned that she only had sex with one man in her entire life(!), that being her ex husband, and that was six years ago(!). She was a hardcore Christian, so much of this made sense. She actually quoted the Bible several times.

My favorite moment came when I found out that because she already had two grown children, she had her tubes tied. Music to my ears! It had been literally almost 10 years since I had actually cum inside a woman. After years of being married to Lacy and having to use condoms for birth control, and after having sex with women like Marci for months since the divorce, always having to worry about condoms and/or pulling out, the thought of cumming inside a woman again was so exciting and wonderful; it stirred a great, biological drive within me.

Regardless, Jenae would be very difficult and I knew it. I knew the odds of actually having sex with her were low, but I thought I was confident enough at this point in my evolution to maybe pull it off.
We ended up meeting three more times (kill me). All four “dates” were things like walking in the park, walking around the lake, talking, and things like that. No “date” stuff. We talked about relationships and sex (a key technique I would later integrate into my dating system), as well as marriage and divorce. She talked about all the other men who would hit on her. She talked about how when she was married, she wanted sex three times a week, which her husband wouldn’t give to her, and how painful that was. (Yeah, tell me about it!) It was enjoyable and I really liked her.

I did not try to kiss her or get sexual in any way during this time. I knew that would likely scare her off, though having four dates with no sex was difficult.

On our fourth get-together, she dressed up. She wore a pretty dress. As we walked around the lake, knowing it was now date number four and way past time to get to the sexy stuff, I finally pulled the trigger. I said something like, “We should relax tonight. We can go back to your place or go back to my place, whatever.” She said “Whatever.” Good answer! I didn’t waste any time. “Let’s go back to my place then. We can watch a movie or something.” She said “Okay.”

I smiled and walked her to my car, trying not to fist pump in the air.

Though I had forgotten it then, I learned a few times prior that in a dating situation, a woman already knows she’s going to have sex with you before the date even begins. She was already planning to get sexual with me that night, or at least was open to the strong possibility. That was the reason for the sudden nonchalant attitude about coming back to my place (something she never would have agreed too prior) and the nice dress.
I was still living in the apartment back then, still waiting on my divorce (the legal part of ended up taking two full years, just as I had anticipated). We got back to my place, and I sat in my office chair in the middle of the makeshift home office where the living room was supposed to be. She sat across from me in my recliner chair. We talked for a bit, and then I remembered how uselessly long I waited to sexually escalate with Marci. Determined not to make the same mistake, after talking for a little while, I walked over to Jenae and just kissed her.

I was reasonably confident she would welcome the kiss, and I was correct. She liked it. I expected the kiss to be terrible; she was six years out of practice after all. To my surprise, it was very nice. My high sex drive started raging as usual, and I was really turned on. She was so cute in that little dress, with her eager eyes and tight little body. I slowly lifted her off the chair and walked her into my bedroom. I expected resistance, but instead, she started leading me. Interesting!

My eyes shot out in amazement when before I even got to my bed, she whipped off her own dress in one quick motion, with no prompting from me, and stood there naked before me. God must love me. Clearly she had given this a lot of thought and was more than ready.

We had sex, and I’ll go light on the R-rated details. She was very tight and bled a little. I had to be gentle, which is always difficult for me. And yes, for the first time in almost 10 years, I came inside. Most of you have no idea what that feels like; to wait 10 years to orgasm with a woman the way nature intended. It’s beyond what words can describe.

One the way back to her place to drop her off, I told her that she honored me by allowing me to be her first man after six years. She gave me a big hug. It was very nice.

We kept seeing each other for the next several months. Remembering how verbalizing everything with Marci didn’t work out, this time I made sure to keep my mouth shut, and didn’t say anything about “our relationship,” whether or not we could date or sleep with other people, or anything else regarding the rules or parameters of the “relationship.” We just spent time together, enjoyed each other’s company, and had lots of sex. It was a great time, my first ongoing relationship of any real length since my divorce.

I kept on with my online dating during all of this, of course. No monogamy for me! During that time, I met several other interesting women, and it was interesting to watch how the relationship with Jenae played out… little did I know that she was my first provider hunter, and I would have to learn how to manage that.

I’ll talk about all of that in the next chapter.

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