How to Date a Phone Sex Worker

Dear Dating Mom:

I’m dating a woman who used to be a phone sex worker. Now every time we are together and she talks dirty to me, I feel like she isn’t being sincere because she has said it so many times to so many different men. She says I shouldn’t think like that but I can’t help it.


You talking to ME?

Dear You Talking to ME?:

From the sound of it, your girlfriend has been retired for a while now and the possibility of her taking her work home with her is minimal. 


In my mind, you should take some comfort in that. That being said, Lord above, what I would give to date a guy who used to be a professional housekeeper. In that case, I’d pray to God daily that he would still feel like every day was a work day, but this is about you right? Sorry.

I can understand how you would feel this way but the problem is she can’t undo what she has told you, and so you’re just going to have to take her word for it that when she says things like, “You turn me on so much” or “You’re so hot,” she really is thinking about you and not one of her customers. 

The advantage here is at least you can look her in the eye and know if she is being sincere. I’m going to gamble that when she is telling you these things, she’s not simultaneously polishing her floors in her favorite sweatpants, like she did during all of her other “love chats."

Also, be happy that at least she knows how to turn a guy on, right? You didn’t mention for how long she was employed in this particular arena, but the fact that she was employed at all, to me, is quite impressive.

I, for one, couldn’t do it, no matter how good the pay. I’m a horrible liar and a little bit, a lot, lazy so depending on the time of day I was working, it wouldn’t surprise me to find myself saying things like, “What am I wearing? It’s 10 o’clock at night and I’m talking to a freak, what do you think I’m wearing? A ball gown? A pair of high heeled shoes and a cape? No, I’m wearing a t-shirt, shorts, and a pair of slippers you f**ing nimwad!”

So you see, there are big advantages to dating this woman or, at the very least, not me.

Of course, if one night, she climbs into your bed wearing a t-shirt, shorts, and a pair of slippers and then begins to tell you how badly she wants to screw you, well then that is when you will know that she is, in fact, being very insincere or at the very least you screwed up something big time and at least for that night, you're not gonna get any.

Are you a single mom with a question about dating/sex/love? Or do you just want to try to trip Jessica up? Leave her a question in comments or you can write to her directly at

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