Has any of your past clients ever fallen in love with you and you didn’t reciprocate those feelings? I ask because the last escort I saw was different from all the other ones I’ve met; she’s very smart, strong, confident, beautiful and she even told me I was cute. She seems to be the kind of person I could be in a relationship with and I would like to get to know her off the clock, but I’ve had so many bad experiences with women in the past that I’m afraid to try anything. What should I do?
As I wrote in “Out of Bounds”, “It’s not at all unusual for a client to fall in love with a whore; sometimes, as in my case, that can actually go somewhere. But there were a lot of men who fell in love with me before Matt, and every one of my sex-working friends has had clients fall for her; it’s a natural outgrowth of a situation in which a lonely man spends a lot of time in the company of a beautiful, alluring woman who only shows him her best side.” But it isn’t common that the whore returns the feeling; I’ve answered a number of similar questions over the years from men in similar situations to yours. And even in the very unlikely event that she does reciprocate and a romantic relationship develops (remember, I was married to a former client for 14 years), such relationships have the same kind of problems as others do, plus a host of special difficulties born of stigma and jealousy.
I’m not telling you that you should run away, nor that a relationship with a sex worker is doomed; I’m telling you that A) it’s very unlikely she feels the same way about you as you do about her; and B) if she is in fact interesting in seeing you “off the clock”, you need to be aware that the relationship isn’t likely to be easier, simpler or more idyllic than any other sexual relationship between two flawed human beings, which is to say “not at all”. My advice to you is the same as it was to the two gentlemen I answered in “A Living Thing” and “Favor” earlier this year, which is: Enjoy what you have with her and don’t try to turn it into something it isn’t. And if she begins to clearly and directly express romantic interest in you, and it actually does turn into a romantic relationship rather than a strictly professional one, don’t go into it expecting it to be all sunshine and fairy dust, because I can absolutely guarantee you it won’t be no matter what you think right now.