And he ended up dropping over 25k on me that month.

Win/Win

Just to give you some variance in situation, I'll give you two different relationships I had.  I dated one as conventionally as you can imagine.  Dinner dates, theater, shopping, movies, nights in just watching tv.  etc..  We dated for about 4 months before it ended.    

Another time, the situation was much simpler.  She would text me and say she wanted to see me tonight.  I would go and pay for a hotel room and she would come over and spend a few hours before she had to go home to the kids.  

These were both massage/ body rub girls.  Remember, these are human beings who have all the standard needs of other girls.  Sure they have jobs that require immediate intimacy with a lot of clients and it always seems as if they are enjoying their work and the "life" but they also need that someone to listen to them and understand their different situations and make them feel special.  Some are very good at keeping the two worlds isolated from each other.  A lot have lines that get blurred.  In the end we all do what we have to get some form of what we need.

10 years ago a provider was here for three months from Europe.  She didn't really know anyone and didn't really like the guy running the business.  She was the sexiest, most beautiful and worldly girl I had met at the time.  We had an awesome affair, and our relationship ended with me sending her several overseas packages full of the green she had cultivated.  Trust.  Lust.  Fun.  Fun.  Fun.  I often wonder what she's up to now, as she went back home and used her hard earned cash for school.  

If it happens, it is always by chance.  Never by design

A few phone calls/e-mails. Mostly of the "I want to talk to someone about this that would understand" variety. I tend to be a good listener and have that whole 'trustworthy' vibe about me, I guess.  

Not that I would have turned down any of these women for an actual date and/or relationship. They were all beautiful, intelligent women who had the added benefit of being damn sexy. I'd see any of them in a heartbeat - if they were out here instead of in Chicago. Who knows - maybe they are (some are retired), but I'd never know.  C'est la vie.

I've done that a few times....

Three times actually.   Had really great chemistry with all of them...and with two of them "saw them" in the business-free realm for a few months or so.   It never went back to client/provider relationship after that, and eventually ended.    

The other client, I only went out with once OTC:  When we met for dinner, he "drank" his dinner, ordered nothing, while I enjoyed mine.  Then the following week he called me like three times and sounded pretty intoxicated every time.....which I thought "no way" am I doing THIS.   Feeling he had a "drinking problem", I never went out with him again because of that.  And never saw him again as a client either.  

: