Tough Love: An Escort on Dating Her Clients
Illustration by nuglybird for Rice. 

Sometimes, I fantasize about dating a few of my clients in real life. Being in a real relationship. For “free”.

Let me preface this by saying that this is a rare occurrence. Most of the time, both parties are very aware of what they are getting into when they reach out to make a booking with me.

But in just about a year of being in this industry, I’ve met 3 people I wish I had met as myself rather than as Rebecca.

A family lawyer, a cafe owner and a freelance writer. To protect their identities, I can’t get more descriptive. All that you need to know is that they came from different backgrounds, but shared one thing in common. When we were together, we were electric.

As cliched as it sounds, meeting each of them felt like reuniting with a long-lost friend. Like we had known each other for a very long time.

We had shared interests, talked about “normal things” like watching La La Land and feeling miserable after, why Coltrane makes for the best rush hour playlist, that new overpriced Nasi Lemak restaurant that’s actually really good.

We shared our plans for the future, talked about our fears – not just serious stuff but banal nonsense like how I’m terrified of birds (brown pigeons, in particular).

Normal shit, essentially. Which to me, is the best part. In their own special way, I felt like I shared with each of them a connection that went beyond the usual escort – client relationship.

with the right person, the line between “business” and affection starts to blur

Perhaps I desire some normalcy. After all, I’m only human. I would like to have interactions where I’m not in “Rebecca mode”.

It sounds insane, I know. Perhaps I’m only feeling this way because Valentine’s Day is around the corner. But being in the business of intimacy, sometimes, and with the right person, the line between “business” and affection starts to blur.

It’s confusing for me because I know I’m supposed to maintain emotional boundaries with clients. Playing the part of a loving, fun girlfriend is not hard, but during times like these – it becomes a little too easy. I don’t act on my crushes because I like to remain professional, but can I really control who I develop a crush on?

When I first realised I was crushing on a client, I panicked. Why did we have to meet this way? It’s so unfair that I meet such an amazing person, only to keep things professional. Why didn’t we meet at a café or bookstore, like in the movies? Things might have turned out different.

But then again, if I had not chosen to be an escort, would our paths cross in the first place? Not likely.

The truth is, I’d rather know them as a client than not at all. I might never be in a relationship them, but I’m happy I met them all the same. This is fact. To me, fate works in mysterious ways that we can’t explain or control. We just deal with it.

I’m sure that I’m not alone in this. Sometimes you meet some unicorns that make you wonder about the possibilities beyond the normal client-escort relationship.

I’ve also wondered whether I could trust a guy who visits escorts

But sadly, dating a client is not an easy decision for an escort to make. The main issues are privacy and trust.

Pursuing this vocation comes with dealing with the stigma that comes with it. Protecting my identity is the most important thing to me. What if we have an ugly breakup and the ex-client threatens to expose my real identity to everyone?

Conversely, it would also be extremely unfair to date a client in a purely non-work context but for him to never get to know my real name or meet any of my friends or family.

It’s a classic catch-22.

I’ve also wondered whether I could trust a guy who visits escorts. Sure, the three guys in question were single when I met them (or at least that’s what they tell me), but what’s stopping them from doing the same if we do actually get together?

I can’t run from the fact that I help married men cheat on their wives and partners. And as hypocritical as it sounds, this has made me less willing to trust men in general.

It’s a job hazard, I guess. So based on my experience, one could say that it’s improbable for an escort to find love.

But I’m not ruling it out. I do plan to do this till my 30s, or when I find myself in a serious relationship – one that leads to marriage – whichever comes first. I’m only 21 after all, and I still have a long way to go.

There is a point of certainty though. I am naturally monogamous, so if a really amazing person (who is probably not a client) comes along – someone that I’d like to spend the rest of my life with, I’d quit in an instant.

Risqué Rebecca is a social escort working in Singapore and is a columnist for Rice. You might remember reading about her from our earlier article on social escort economics. 
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