The evolution of trust in paid dating

Some time ago, I wrote a bit about how trust evolves in virtual relationships.

I thought I’d write a bit about how it evolves in commercial sex (or at least, how it did for me), since I suspect that’s actually an area with which fewer of the readers of this blog have extensive experience.

Here’s how it worked for me.  I connected online.  Once in a great while I connected in real life with a woman I met in a massage parlor in an ongoing way. It once was possible to meet women on Craigslist, but by the time I had stopped paying for sex regularly, the main way I did it was SeekingArrangement, a God-awful, inexplicably inexcusably badly designed web site.  After a couple of messages on the web site, and then typically graduating into real e-mail, I would arrange to meet – for a drink, a meal.  By this time (3-5 or more messages in), I had a pretty good sense of whether we could possibly hit it off.  People tend to be very communicative via e-mail, very efficiently, about who and how they are in real life. In my experience, by the second e-mail, people generally have communicated whether there might be a “there” there.

Something like 90% of the women with whom I first discussed making a concrete plan flaked (or revealed themselves to be terminally unreliable) before the moment of the actual plan.  This might have been by disappearing during the e-mail phase, it might have been by making a plan and then rescheduling six times, it might have been by having a grandparent die or a family emergency, it might have been just by not showing up at all.  But once in a while – a woman would show up.

We would have a conversation.  Maybe it’s meta – about both of our experiences on the site.  Maybe it’s more direct – what she likes, what I want.  Maybe, at the end, we kiss.  Maybe a little more.  Typically, I would offer a bit of money – a token of my appreciation, to indicate “good faith,” consideration, etc., to show that I appreciate that I have, after all, gotten something:  the opportunity to share some time with, and be seen with, an attractive, typically younger, woman.  Occasionally, women would demand an up-front payment simply for the privilege of meeting with them. Invariably, my response to this was to walk away.  While I was prepared to show some appreciation for someone’s sharing some time with me, and to recognize that in fact there was some value to me simply in sharing a drink or meal with an attractive woman, I wasn’t prepared to agree in advance to pay someone to interview her.  And after all, this was something of a job interview.  (In my experience, I never was paid for a job interview, but hey….)  And I always had the sense that there were more than a few women for whom such “compensated dates” were what they ultimately were seeking from the site.

In any event – then, we would meet again, if we hit it off.  Typically, the second date would be a bit more intimate.  Sometimes, not.  Sometimes, it would be a second chance to “get to know one another” before a third, more intimate, date.  And again, if it was one of those platonic dates, the second date typically would be “compensated” as well.  But by this point, by the time I’m on a second date, I’m typically in a somewhat different zone with the young woman:  my experience has almost always been that, with women I meet twice, I’ve established enough of a rapport that we now have some fellow-feeling, we treat one another with respect.  I’m tempted to make a sort of Seinfeldian proclamation about the social obligations we have to one another at this point.  I, having shelled out some money, twice, am owed something by the woman.  Not in the way of sex – no, that’s always at her discretion.  But decency, politeness, respect – not standing me up, or disappearing, but rather, interacting as if we’re the friends that we’re (feigning?) becoming.

The woman, having twice given up a significant chunk of time for, let’s face it, substantially less than she might be making in a more intimate setting, is owed something by me – again, not money, not a “guaranteed arrangement.”  But decency, respect, politeness.

Typically, by the time we actually would go to bed, we would have a relationship that looks not unlike that of friends in these ways – we would know a bit about one another – albeit a circumscribed, and particularly “performed” bit; we would presumably like one another – of course acting always is a possibility, and performance of some sort a certainty, but I don’t know that I ever have gone to bed with a woman I didn’t like, and I sure hope the opposite is true; and we would not just like one another, but have a fundamental respect for the other, and desire to treat the other with decency.

I may be idealizing, or imagining, the motives and feelings of the women with whom I had compensated affairs, but I honestly don’t think so.

This is how it worked for me. How does that compare to what you imagine when you imagine men paying for sex not from “escorts,” but from “sugar baby/sugar daddy” type relationships?

There’s a whole ‘nother post to be written about the economics of such relationships, as well as one about the longer-term development of those relationships, and maybe I’ll do those some day.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.