A male sex work client is in bed with his female escort as his wife tries to call girl on the phone.
Infidelity, a huge crush, and poor emotional boundaries are a recipe for disaster...

"How do I choose between my girlfriend and my escort?"

Georgie Wolf
Georgie Wolf
Content warning: this article discusses stalking. If you find this topic distressing, you may wish to hit the 'back' button.
I literally, just came across your website tonight, as I search for answers to my serious dilemma of my feelings for an escort, while I'm also in a long-term relationship of 21 years.

I'm 47 years old, and before my current relationship I had been clients of massage attendants and escorts. I was faithful for the first few years of my relationship, but about four or five years I went back to doing it on the side. I never allowed any of these ladies into a personal relationship situation.

Recently, my personal life has been kind of rocky. From arguments over money, not being on the same page sexually or intimately, and of course her not wanting to do anything socially due to COVID. I still love her and don't want to lose her. But.....last year, while looking at some ads during lockdown, I came across this absolutely beautiful, 20-something escort. When things began to return to normal, I booked with her when she came to my city. We clicked. Then, once a month, it became my special treat.

Just before we went into another lockdown in 2021, I decided to invite her to breakfast and she accepted. Our date was off the clock (and no fee). I paid for all food. For some reason, right around then, I began to notice myself beginning to "cross the line" of developing feelings for her. Honestly, days would go by and I couldn't focus on things.

A few months later, I contacted her for a multi-hour date (dinner, sex). She said it would be $600. I was conflicted about a lot of things. Do I try to juggle two women? Do I tell her how I'm feeling? Well, after our date we had a long heart to heart. I told her how I had been feeling. She told me that she enjoyed my company but made it clear that she never dated while working as an escort.

We never had sex that night. It was an emotional overload for both of us. I asked how much I should give her for the night, she said honestly don't worry about it. The next few times I texted to see how she was doing or to try to get together...no response.

Last week, I wasn't sure what to do. I decided to book anonymously from a texting app. Upon entering, I could tell she looked a little annoyed. We talked out a few things and both felt good about our chat. I had one of my usual bedroom sessions (paid her hourly rate, plus a tip) and afterwards she asked me to stay, as she packed to head home.

As we embraced in one of those hugs where you're not sure when you will see the other person.....she looked at me and said, "When will I see you next?" I told her, 'That is entirely up to you. We laughed and made a joke or two, then agreed that we will figure it out.

I'm very conflicted, and all over the place. I have feelings for both women.On one hand, I want to be able to be selfish and juggle things. I know that is going to be a recipe for disaster at some point.  At the end of the day, I think my current fling will burn out at some point, but right now the flame is getting hotter!

Any thoughts, guidance or words of wisdom would be greatly appreciated.

Sometimes we do things that make ourselves miserable, even when we know it's a bad idea.

We may have a hunch that we're on the wrong track...yet we ask friends for advice and obsess over our problems, rather than simply walking away from a bad situation. I suspect this might be the case for you.

You've talked about being unhappy in your relationship and having feelings for your regular sex worker. You're worried about who to choose. You're uncertain as to whether your provider is open to a romance outside of her work.

It's tough love time. Nothing I have to say here is good news...but, hopefully, you'll find it helpful.

Fact #1: Escorts don't date their clients.

Although you feel a connection with your worker, it's clear that there's no chance of a real-life relationship.

You've made a lot of assumptions about how she feels, but you only really know how you feel. It's a sex worker's job to help you get comfortable, to make sure you both 'click' during your sessions. This doesn't mean their kindness towards you is necessarily fake! But it's a service. Her affection toward you is part of the experience you're paying for.

Escorts don't generally date their clients. Sure, you might be hoping that you're the exception to the rule. But your worker has made it very clear to you that she doesn't want a relationship. She doesn't date 'while working as an escort'. There's no need to agonize over the possibility. You already have your answer.

Fact #2: Ignoring a 'no' is unacceptable.

There are a lot of poor boundaries here. You've been hanging out with your provider off the clock, swapping text messages between bookings, and generally letting the line between 'professional' and 'friend' get blurry. Regardless of her role in this, it's your responsibility to keep your distance. You need to remind yourself that it's a professional relationship and avoid interacting with her in ways that blur the boundaries for you.

When she stopped replying to your messages and wouldn't accept your booking request, that was your signal to move on and see someone else. Instead, you made a booking by hiding your identity. This is not okay. When you've been refused by a provider, booking anyway using false details is a huge consent violation. It's happened to me in the past - it feels scary and invasive.  Your provider may not have felt safe enough to tell you how inappropriate your behavior was...but I suspect she wasn't happy. Turning up on someone's doorstep without permission is literally stalking. Please, never, ever do that again.

If a sex worker stops replying to your booking requests, they're telling you 'no'. You must respect that.

Fact #3: You're in charge of your feelings.

A lot of people think that romantic feelings just happen to us. We talk about being 'swept away', as though we have no control over who we fancy and how we behave. But the truth is, we do have control. It's your responsibility to decide what feelings (and which people) you focus on.

You're obsessing about your unrequited affection, trying to convince yourself that your professional relationship with your provider might turn into a relationship. But this is making you distressed. The solution is simple: find other things to do. Quit trying to see someone who can't give you what you want. Once you stop feeding the fire with repetitive thoughts and constant efforts to contact her, your feelings will fade.

It's time to make a choice...

You're stuck between staying in your unsatisfying relationship or pursuing a sex worker who isn't romantically available. Neither is a good choice. Luckily, there's a third option: just walk away.

I don't need to be psychic to see drama in your immediate future. Whether your infidelity is discovered or your provider takes further action to protect herself, this train is about to crash. It's nowhere near as fun, but perhaps you should consider seeing a sex-positive therapist, to figure out what you want in a partner. With some professional backup, you can search for a life partner who better meets your needs.

You have a bit of personal growth to do, too. Honesty and respectful boundaries are essential for a healthy relationship. Therapy can help you master this stuff....so that, hopefully, when you do find the right person, you'll be able to hang on to them.