06 / 03 / 2018
5 Minute Read

Should you date an escort ?

Most men would probably not even consider such a scenario. For most men, even those who use escort services, there is no way they would allow themselves to have feelings for a woman that has had, and is having, sex with a multitude of other men.

I understand them fully. There are so many insecurities being trampled on in such relationships. Tons of questions come up. What if she is recognized in public ? Who wants that coy smile from a stranger as he’s judging you based on her choice of careers ? How can I compete with all those other men ? What if I am one of many she is dating? How can I tell ? Aren’t I exposing myself to STDs ? Why would I share my lady with anyone else ? Etc, etc, etc…

I’m on the doorstep of my fifties, single, no kids, and I have dated escorts on many occasions, and would do so again provided the lady was worth it. Full disclosure: I would, and have, dated escorts, but always with the understanding that if we wanted to go beyond dating and become a full-fledged couple, she would have to give up the business.

Now let me address those many questions/insecurities.

Men are hardwired to be jealous of physical intimacy; for good reasons. We men, throughout our history, could never be sure that our offspring was actually ours. The natural instinct is thus to guard access to our mates so as to not raise illegitimate children; it defeats the purpose of propagating one’s DNA.

Therefore, having your lady share physical intimacy with other men, for money, will evoke a visceral reaction that is tough to tame. DNA testing eliminates the risk as far as kids go, but the fear of being one of many in her dating pool is understandable, although irrational, because even in a normal couple, you can never be sure either. It’s always a leap of faith. You might be sharing a lady and not know about it. The fact is you are always implicitly in competition; you have to be confident of what you bring to the table.

The embarrassment you could be exposed to if she’s recognized in public is really of your own making. Why should you care about a stranger’s opinion ? What if you met a normal girl and were unaware that she’s been with countless men before you ? The only difference would be that, at least, your escort/lady was upfront about it and she got paid. Most promiscuous normal ladies usually have serious self confidence issues that should worry you a lot more anyways.

As far as STDs go, the fact is that, except for streetwalkers, most ladies in the sex industry get tested on a far more regular basis than the general population and they always use condoms; how many regular girls can say that ?

Now the hardest argument to dismantle; why would any man accept to share his woman ? In a perfect world, you shouldn’t. But this is not a perfect world. You can’t let perfection be the enemy of the good, or you may walk right by a truly great experience/person.

Exclusivity is big part of the value of a relationship; everyone wants their own sacred little garden. It is not ideal when your partner is or was an escort, because the physical intimacy club has too many members. However, the club that should be very exclusive is that of her heart. That’s the one you want to be a VIP of. Sex is sex, but if you give true passionate love away like candy on Halloween, what is that special feeling of being The One worth ?

I have had 3 relationships with escorts. Ranging from dating to it’s complicated...

One was with a university student that gave me her phone number after our first escort/client encounter. We would meet a couple times a month for dinner and torrid overnight stays. Then one day, she graduated, told me: “We are not at the same stages in our lives...and I don’t regret any of the time we spent together”; she hopped on a plane, flew across an ocean and I never heard from her again.

Another was a regular escort on my list; then one day, we bumped into each other on the metro, she recognized me, we started chatting and seeing each other every now and again. Her life has been a series of dramas. She got sick, got better, let herself go and let’s just say the bloom is off the rose now...We still have those long talks once in a while, but that’s it.

The last one was just a thunderbolt. On our first escort/client encounter, she point blank asked me if I would date an escort, to which I said yes; we exchanged phone numbers. I saw her once more as an escort after that, then never again. We only saw each other socially. To be honest, I thought she was The One; truly the best combination of all the attributes I love in a woman. I thought if God blesses with kids, I’d want to see her face on them... but I was the only one carrying water on that count. It happens…

And that is exactly the point. It happens. I found three of the most beautiful flowers growing in what many people would call manure laden mud: the sex industry. Imagine if I had been obtuse and passed on these 3 ladies.

I would have missed out on a great 2 years of the best sex I ever had with that foreign student.

I would have missed out on 10 years of great conversations with a refined lady.

Worst of all, I would have missed out on 8 years of a woman whose mere presence makes me happy.

I’m still single, no kids, almost 50. I didn’t land the relationship that I wanted with either regular women or escorts, but I sure had more memorable times with the latter than the former.


J.R. for TheVelvetRooms

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