Dear Sasha, I’m a 30 year-old gay man who in over a decade of being out has never dated or had a boyfriend. The last time I had sex was three years ago. The time before that was four-and-a-half years ago. I can’t remember what a kiss feels like. I’ve “been myself'” for three decades and it’s not working.
I’ve started thinking more and more about hiring the services of an escort for a boyfriend experience. I’m thinking of an overnight session that lasts into the next morning involving a lot of role-playing: him literally pretending to be my new boyfriend who’s in love with me. This wouldn’t be too scripted but it would include experiences I’ve never had (going out to dinner or a movie, holding hands, flirting, saying/hearing “I love you,” waking up together etc.).
What can I realistically expect to get out of the experience if I do go through with it? I’ve accepted that I’ll never find love. I’m simply hoping for a little comfort, relief and pleasure, even if I’m not entitled to it for real.
-At My Wit's Fuckin' End ?
Dear Wit’s,
This deliberately hopeless attitude isn’t winning you any potential boyfriend points, but if that’s not enough to send you flinging yourself all over a chintz divan, longtime escort Logan has some firm words too.
“I’ve never had this asked of me directly but it does go with the territory in general, usually with repeat clientele,” he says. “The going to dinner/movie, flirting is what escorts are paid to do: ensure the client has a great time. The ‘feeling’ of being in love may just come out of that without asking directly for those words.”
Though Logan himself is a trained actor, he says he would, “seriously doubt my capacity to pull it off with any amount of sincerity. But if this is what he is looking for, my advice would be to call around and find someone who would be willing to go for it. Meet with the escort, paid of course, and get a sense if they are comfortable with each other and if the escort is going to come anywhere near his expectations. Make sure the escort—and he himself—understands that this is role-playing and it’s not going to turn into something creepy. The minute I hear the word ‘love’ from a client, the red lights start flashing and I head for the door, but if it’s part of the fantasy, that’s a different story.”
What can you realistically expect from the experience? “Paying someone for a little comfort, relief and pleasure is very reasonable,” says Logan, “Most escorts should have no problem at all with that request. Paying someone to sincerely tell him they love him and him believing it in return is a very tall order in my opinion and should it fail to meet his expectations, which I’m guessing it will by the line, ‘I've accepted that I will never find love,’ he may just find himself a little more bitter than he already is. No one in this world is ‘entitled’ to love whether they pay for it or not.”
Logan dusts off his Hamlet and elaborates, “We know what we are but know not what we may be. Instead of looking at himself as the reason he’s not connecting with people, he has this ‘take me as I am’ approach and blames the world for not loving him as he is. Bullshit, I say. If you’re not getting what you want in life, look at yourself and see what it is you can change or improve on. If he thinks that paying someone to pretend to love him will in some way comfort his sorry ass, he’s just pouring salt on an open wound. His next letter to you will be what a failure the escort was at his job, I’m sure.”
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