Dating an escort - can it work?

Hi there,

I feel I could use some advice, sorry - it's a bit long winded but here's the background:

Over the past few years, I spent some time on and off using escort services. I ask that you don't try to judge me for this. It's something I chose to explore (it is legal in my home country). I often work long hours, so when I haven't been in a relationship, it's something that I found helped me.

It all started when I met with a working girl a bit over a year ago. Let's call her Alice. I saw her a few times over 2 months, which is unusual as I am normally not inclined to make repeat visits. I liked her though so was interested in seeing her more. Soon she started to contact me (on a number I gave), saying she missed me each week. I started to get a vibe from her, one that I normally get from someone interested in going out with me.

Initially I felt perhaps she was just playing me a little. I'm not exactly new to this. I thought she saw me as a good client who could provide repeat business. I wasn't 100% sure though, normally I can detect false affection. I hadn't felt like this with other escorts I'd spend time with.

Each time we met, she would get excited that I had returned to see her. The staff at her place of work noticed. They treated me nicely and I was told they would reduce the cost for me to continue to visit Alice. I started to wonder if she did have real feelings for me as she seemed genuinely interested. My intuition/gut feeling was telling me the vibe was real and she liked me. My rational mind decided that in this case, money was involved, so it was more likely just an illusion created to keep me coming back.

I started to get a little concerned. Even if Alice was genuinely was interested in me - I was uncomfortable in letting myself explore an interest in Alice. My concern meant that I decided to back off and stop going to see Alice. I ignored her requests to come and see her and eventually she stopped trying to contact me.

At the beginning of this year, I noticed Alice stopped advertising. I found I often thought of her. I wondered if any of the cues I felt from Alice were real. I wondered whether I had hurt her by not returning.

My mind wouldn't give it up. I decided to ring to see if Alice was still working. She was. I waited a while but my curiosity won and I decided to visit her again. The visit was slightly awkward... Alice acted a bit weird. It was like seeing a past girlfriend who I had ignored. She seemed happy to see me but now she was more guarded and a little distant. I left after that visit feeling bad, that maybe I had ruined a good thing. I didn't go back again ... until more recently.

A few months ago, my thoughts were again filled with the desire to see Alice. I wanted to see how she was. I went and saw her and when I arrived, she was overjoyed to see me.

Alice seemed really happy and I was feeling more and more that this wasn't some kind of false affection or facade.

This time, I decided to see her again soon she was super happy. She gave me her personal contact number and asked if I would like to go out for dinner. Now, I realized that her interest in me was quite likely to be real as she wants to spend time with me without money changing hands.

I've been seeing her over the past months and I've come to a crossroads as to whether I should let this continue. I can see myself really falling for her. Part of me wants to explore a serious relationship with Alice, she is really nice and I don't quite understand why she's working in the industry. Part of me is scared and I wonder if I'm in for a world of hurt.

I'm a little skeptical that it can work. I'm ok with her line of work at the moment but longer term I know I wouldn't be. I haven't really talked to her about her work as it seems a bit personal. I know she doesn't want to continue in this line of work forever, she's taking courses to get started in a new career. I just don't know how long it'll be before she's decides to really make a switch. I'm not out to save Alice - she obviously has chosen her own path and she is independent and I respect that. I do wonder where things would lead if I continue seeing her.

We are of similar age (30ish) and I'm at the point now where if I commit to a new relationship, I'd like to make it work. I've been in relationships before, some shorter term and one very long term one.

Maybe this is just a bit complicated? Aside from the risks of her job, there are also questions I can't answer. How do I introduce her to friends? My mother?

I guess I need to talk with her and see what she wants from the relationship. If we both want similar things, maybe I should just go for it?

You have no right to judge her as you reason you met is because you wanted to sleep with a prostitute. This is a really sleazy story. I think you two are perfect for each other!

Have you had sex without paying or are you taking her to dinner AND paying to get laid?

It's almost certainly a doomed relationship, unfortunately. Unless she's ready to move on to a career things can't possibly work in the long run. Whether or not you're paying determines whether or not she actually has an interest in you or she just sees you for a nice sucker whose company she doesn't mind so long as she gets her money and a free meal out of it.

I was in a similar situation years ago, only worse. We were on-again/off-again for years. After I got personally involved with her, I gradually figured out that she was a meth addict. She wouldn't quit her job or the drugs until she got arrested and had to clean up. She later got back into that work and ended up with a drug dealer and they both got hooked on heroin.

Anyway, at one point when she was desperate and I couldn't help out any other way, I drove her on outcalls a few times. Sitting in my car outside suburban houses, knowing she was having sex with some guy inside... I felt low. Think that scenario through, and decide if you can handle it now, before you live through it.

When she finally ended up in prison for 8 months, I decided that was the end. I wrote letters to her while she was in prison, encouraging her to make some better choices when she got out. And I started dating again. I met my current girlfriend, and we've been together for seven years now and are still happy together.

Yeah, it never,never land it might!