Arrangements Gone Wild

By June I had gone through an intense love affair.

I threw myself into work as therapy. But I found myself looking toward finding another arrangement. Perhaps not the wisest coping strategy.

I threw a lot of caution to the winds in enlisting into Arrangements. I now see it as an illuminating self-destructive behavior. I had convinced myself in February 2010 not to stray from my Arrangement criteria. Yet I regressed and did exactly that.

In the six months between August 2010 and January 2011 I engaged no fewer than four Arrangements. I broke several of my Arrangement rules.

Those Arrangements do not include the two earlier Arrangements where I had still the one year economic contract to pay out. One of those I had to extend on a hardship basis. Her economic situation was dire. And she was in the middle of a school commitment.

I also went through a few reconnections with woman I had met earlier. Some were candidates for previous Arrangements. I reconsidered because I had broken some earlier Arrangement rules. I did so in a manner both unlike me and sometimes unbecoming.

I had never done anything like this before in my life.

Arrangements

Lana was a woman with a profile both taller and older than my typical preference. She had two children one year apart from teen pregnancies in a bad marriage. Her parents had passed away early. She had raised her kids to teens on her own, worked as a successful enterprise salesperson, had done some part-time modeling, and through she was in her late thirties she looked stunning, partly due to half-Asian genetics. Her previous business had tanked in the last economic crises. She was eager to start a new business and had the Project business plan all set. The Arrangement started well. She was a survivor, independent and headstrong. But her time commitments to raise her children, manage the business, remain in the southeast nowhere near my travels, and a number of other things made it impossible to actually meet more than a few times. So the Arrangement quickly terminated by mutual consent though I maintained my investment commitments to her business.

Tara was another single mom, still in her twenties. Her interest was getting out of the debt trap being in Las Vegas and a set of dead-end service jobs and starting a photography business. Her talents was quite obvious given her ability to create strong photographs with relatively simple camera and studio equipment, Photoshop on an ancient Macintosh, and a lot of creativity. She had never had an arrangement and in fact had only recently freed herself from the deadbeat father of her children. She was very eager to follow my lead. But her fear of rejection from the windfall that I represented was worrisome. This was compounded by her bipolar condition. Though treated with medication I saw incipient instability. If the emotional attachment grew too strong I worried that there would be a messy breakdown. So ending it early, though itself a messy process, was the expedient and appropriate solution. Again I maintained my investment commitments to her business.

Bella was an attorney in her twenties highly connected to the tech world though mostly artistic. A fantastic writer her interest was in starting a business consultancy. She actually had started one in New York that specialized in labor negotiations but needed assistance in expanding it, in particular into the higher growth areas of technology sector. She had two previous affairs with older married men who had created a lot of opportunity for her. Bella perfectly understood the limited temporal nature of the Arrangement. But she felt strongly she wanted to be connected strongly to my principal business. She was more service oriented. She did not have strong entrepreneurial goals of her own. She wanted to serve my goals. She was a submissive, very much reminiscent of the female character in movie, The Secretary. I retained her as a consultant to one of my businesses and detached on the relationship side over several months. She remains a paid consultant that adds value to one of my businesses.

Sara was a mid-twenties Chinese graduate student in her final year at a top California school. Young, pretty, and intensely ambitious she had already started two energy companies and started working on major deals between US companies and her extensive Chinese connections. A true dynamo in personality and drive, and yet seemingly innocent, she was able to charm professors, politicians and executives into helping her extensively with contacts and references. Sara had great ideas and no sense of limitations. In other words a perfect entrepreneur. She had a charming oral fetish and a princess syndrome. I helped her with two major projects and fundraising. Though to be truthful she did it mostly on her own. As a natural consequence of these she relocated to China. She was kept so busy that the conversion of the relationship to more distant was natural.

One could ask why I chose these women. It was a combination of their needing or liking me and their physical attractiveness. In retrospect I may have rebounded from Yu-na by seeking acceptance and validation first and foremost. This theory is reinforced even more by my breaking a cardinal rule I had about Arrangements: exclusivity. In these cases I maintained the option of having more than one simultaneous Arrangement, and, in fact, even some dating on the side. In the past my Arrangements were entirely exclusive: while in an Arrangement I would not see any other woman. While I had one or more of the Arrangements noted above, I also was seeking alternatives. This is the main danger, I think, of eschewing exclusivity. Too much seeking of alternatives, leading to restlessness and focus outside of the relationship.

Arrangements Revisited

I had hooked up with five woman who were previous Arrangement candidates. These are women whom I had interviewed in the past. One was an actress in Los Angeles who had a few major movie minor role credits. Another was a model now turned business development person for Asia business. A third was an contracts attorney at a major California high technology law firm. The last two were Asian women whom I had met at high end room salons in Asia. One was taking a graduate degree in economics. The other planning to take an MBA in Australia and brushing up on her English.

These weren’t proud moments. I knew of their interest in me. I met them and wined and dined them. I slept with them for the first time. I had not slept with them in the past during their candidacy. So they were all one-night stands. Perhaps not literally one night, but whatever time I spent with them, that was the last time I spent with them. Sexual trysts that gained neither party very much.

I also almost hooked up with three other women I had met through the Arrangement process. One was a 20 year old blonde ex-model and student. She had a boyfriend that had proposed to her, but she was indecisive. Another was an MD-PhD student in her mid-twenties at a reputable east coast medical school. She was thinking of adding an MBA to her already overloaded diploma collection. A third was a 20 year old Asian architecture student. She shared elaborate and open-minded sexual fantasies over phone and email. I did not end up bedding these women. But I came uncomfortably close.

On the exciting side, the lack of inhibition about longer term engagement gave a lot liberty to try more daring things more quickly. I was often surprised how willing my partners were in these initial sexual encounters. To role play, for rough sex, public sex, threesomes, swinging, creative videos… whatever. Nothing truly new to me. But novel in happening so early. Often during our first or first few sexual trysts.

I felt a bit numb about these encounters. I enjoyed them. I enjoyed the women. But there was no lasting positive experience. Conversations weren’t lively or active. They weren’t competitive at all with work. And I started to feel like I was taking advantage of the emotional needs of these women. I started to suspect they were merely filler for the hole left by Yu-na. That the compromises in my Arrangement rules were my subconscious guarantee that these encounters would never be successful or fulfilling.