Gettin' Down in Chi-Town
The Escort Talk
Dear Lucy,
I have been working as an escort for the last 6 months. And while I love my job, I have become terrified to enter into any boy/girl-friend relationship for fear of possible repercussions it would have, specifically, if my friends and/or family were to find out my career choice.  If I do decide to start a relationship with someone, I can’t imagine lying to them about such a big part of my life. When and how would you tell a prospective lover, with the least risk of being outed?
This is a toughy. I really see no option but to tell your potential new partner about your career choice BEFORE the first time you sleep together.
Lying is not on the table here, and I’m glad you can’t imagine yourself doing so. If you don’t tell the person you’re dating what it is you do for a living, they’re going to wonder. Especially if your job involves going out at all hours of the night. If you’re interested in a “real” relationship with someone, it will have to be built on trust, as that is the only way for any good relationship to survive.
When you meet someone that you’re interested in starting something deeper with, you’ll have to start slow. It’s easy, in our society, to jump into bed with someone first, then learn about him later. Believe me, I’ve done it many a time. But with a big piece of sensitive information like yours to drop on a new love, you should be sure that he is the one you want to reveal yourself to. Go on many dates before having sex. Make out and mess around, sure, but no sexual acts involving fluid exchange until you’ve decided that he’s worth having the Escort Talk with.
So let’s say you find the guy you’re ready to trust with this important fact about yourself. Well, you say you’re very concerned about your friends and family finding out about your job- this is why trust is so important. Tell your dude that you really like him, and that you’re interested in going further with your relationship. But before you go much further physically, you want him to know something private about yourself. Stress to him that this is NOT something you discuss with your friends and family, but you like him and trust him, and you want him to feel the same way about you.
Then it’s really a toss up as to how he’ll react. If you present yourself to him confidently and matter-of-factly, he’ll probably react better than if you act scared and sheepish, or even ashamed. He may decide that he’s not able to have a girlfriend who is an escort. But you have chosen a risky profession, and this is one of the risks you have to be willing to take.
I’m not sure what your reasons for escorting are. Maybe you find that it’s the best way for you to survive financially, or maybe you just dig the job. I think it is totally possible to find a guy out there who won’t freak out over you being an escort, maybe he’ll be turned on by it too! Or maybe you’ll find yourself feeling something deeper for a client, Pretty Woman style. But if you’re having a ton of trouble finding a guy who’s ok with your job, perhaps you’ll need to decide if that job is worth keeping.
Xoxo, Lucy

The Escort Talk

Dear Lucy,

I have been working as an escort for the last 6 months. And while I love my job, I have become terrified to enter into any boy/girl-friend relationship for fear of possible repercussions it would have, specifically, if my friends and/or family were to find out my career choice.
If I do decide to start a relationship with someone, I can’t imagine lying to them about such a big part of my life. When and how would you tell a prospective lover, with the least risk of being outed?

This is a toughy. I really see no option but to tell your potential new partner about your career choice BEFORE the first time you sleep together.

Lying is not on the table here, and I’m glad you can’t imagine yourself doing so. If you don’t tell the person you’re dating what it is you do for a living, they’re going to wonder. Especially if your job involves going out at all hours of the night. If you’re interested in a “real” relationship with someone, it will have to be built on trust, as that is the only way for any good relationship to survive.

When you meet someone that you’re interested in starting something deeper with, you’ll have to start slow. It’s easy, in our society, to jump into bed with someone first, then learn about him later. Believe me, I’ve done it many a time. But with a big piece of sensitive information like yours to drop on a new love, you should be sure that he is the one you want to reveal yourself to. Go on many dates before having sex. Make out and mess around, sure, but no sexual acts involving fluid exchange until you’ve decided that he’s worth having the Escort Talk with.

So let’s say you find the guy you’re ready to trust with this important fact about yourself. Well, you say you’re very concerned about your friends and family finding out about your job- this is why trust is so important. Tell your dude that you really like him, and that you’re interested in going further with your relationship. But before you go much further physically, you want him to know something private about yourself. Stress to him that this is NOT something you discuss with your friends and family, but you like him and trust him, and you want him to feel the same way about you.

Then it’s really a toss up as to how he’ll react. If you present yourself to him confidently and matter-of-factly, he’ll probably react better than if you act scared and sheepish, or even ashamed. He may decide that he’s not able to have a girlfriend who is an escort. But you have chosen a risky profession, and this is one of the risks you have to be willing to take.

I’m not sure what your reasons for escorting are. Maybe you find that it’s the best way for you to survive financially, or maybe you just dig the job. I think it is totally possible to find a guy out there who won’t freak out over you being an escort, maybe he’ll be turned on by it too! Or maybe you’ll find yourself feeling something deeper for a client, Pretty Woman style. But if you’re having a ton of trouble finding a guy who’s ok with your job, perhaps you’ll need to decide if that job is worth keeping.

Xoxo, Lucy

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Life. Love. Lust.

I'm Lucy. I live in Chicago and I like to talk about sex. Give me a topic: I'm happy to answer any questions about love, sex, and relationships. Email me at LucyRockwell@gmail.com


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