A
male
age
51-59,
anonymous
writes:What advice is out there for dating an escort. She is in love with me that I am certain, I know I am crazy in love with her. We were friends before we started dating so I knew what she did for work but as things got more serious what use to not bother me now is starting to weigh on my mind and thoughts and its becoming harder and harder to as i fall deeper in love. What advice might you have for dating a sex worker and what do you suggest nt to do. To save you some trouble I have already ruled out asking her to quit. "if you love me how can you sleep with other men" question is not relevant for me, its more about the not knowing that side of her life in which everything Ive read so far tells me I need to better understand her work. How do I do that if i dont know whats going on? Thank you in advance
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female
reader, anonymous, writes (1 September 2020): The only thing you know about this woman is that she earns her living selling sex - so shes young and good looking and good at sex - end of. She might hate children, she might hate sitting around watching a box set when she could be out and about picking up men instead, she might be a terrible cook, dirty and slovenly and untidy around the home and very boring.
You will not be the first one who had ideas of her being his and being special with him where he can feel far more important than the others she goes with. But for that to work you have to be special and have more to offer than them. Think about what you can offer her that they do not. Gifts will not work. She is not going to sell herself short and make do with gifts instead of the usual fees.
Lots of men become infatuated with a woman. I knew a guy once who fell in love with a famous singer. Of course it was not really love, he just "loved" her because she was gorgeous and on television etc regularly. But he fooled himself into believing that he would date her and marry her. He made a total idiot of himself. It never occurred to him that he did not have enough in common with her.
She could get someone better looking, richer and more sparkly. She could pick and choose from loads who had more to offer.
Eventually he got married to a woman who was a shadow of the famous singer. Sort of an amateur singer with no talent who sang at karaoke evenings for free. She did not look gorgeous either. But it is because she was ordinary and nothing special he had a chance with her. They were on the same level, equals. Both had ordinary jobs, both had ordinary personalities and looks.
That is what you need. The rest is a pipe dream.
Some men take sex workers on holidays with them, but then it is normal for the man to pay her so much a day for her to be there, seeing as it is work to her and she would have been earning at least that if she had not gone.
Many women would refuse to go anyway as they prefer to be near friends and family and have time off and see other people and feel it is safer.
A
female
reader, anonymous, writes (1 September 2020): I cannot see why a mature Worldly woman who earns a lot of money and has men drooling over her would want a boyfriend in the first place. She would be far better off if you were a client where.
Women who get men paying them for their company are very confident, they value their time, they get easily bored, so why would she pick you to fall in love with and make such a wonderful exception for?
I am sure you are not very handsome, very well dressed, in a terrific job and buying her expensive gifts all day - and that is the type of man a woman might make an exception for. Otherwise she is is better off charging you so much per meet and having far more spare time to sell to other guys.
You don't come across as the sort of guy a woman would fall in love with if she is popular and confident.
Sounds to me like you are one of her paying customers, she is a prostitute, and you have delusions and hopes of more.
You would not be the first one. Many men think with their thing instead of their brain.
One of the things you said made no sense. You said you needed advice on how to date her - yet you also claim you love her and she loves you.
Why would you need advice on how to date someone if you are already in a relationship with them and have already been dating them? I need advice on how to date someone is when the person is a stranger to you, someone you barely know, not someone you are in a relationship with and where you love each other.
Instead of asking about how to date her you should be asking yourself why she would want to?
For you it is a way to get more from her without paying. For her it makes no sense.
It would be like saying to a car mechanic that you want him to repair and service your fleet of cars regularly and quickly but instead of paying him you will tell him you like him and buy him a pizza and fries now and then.
Like nobody else has ever tried that stunt with him before.
It dents your ego if you pay for sex so you prefer the idea it is a relationship.
If that is important to you then you must find a woman who does not have lots of confidence and is not that popular. She may be twice the age as this one, she may be fat, with a wonky eye and wooden leg, but then she will not be able to toss you aside and say no to you because she has terrific men queuing up for her. She will be in the same boat as most where her options are limited so she has to consider you more seriously.
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A
female
reader, anonymous, writes (27 August 2020): You're setting yourself up for failure. This woman is not girlfriend or wife material. You are just hoping she will be. You're trying to convince yourself so that you can keep her in your life because you're so infatuated with her. Believe me, it isn't love. You're in love with a fantasy. And she's a fantasy maker. But you're only fooling yourself in the end when you wake up to reality and a broken heart. Turn off your lust and turn on your common sense. The harder you fall, the harder it will be for you to share her. Because that's what you're doing now and always will be doing if you accept the situation. Frankly you should ask her to leave her work if she loves you. That's how it should be. But you know as well as we do that she won't give up her job for you. That's all you need to know.
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A
female
reader, anonymous, writes (26 August 2020): You say you know she loves you. Not sure how you can know this as most of the work of a true escort is making men feel special so they are eager to pay again another day. They are actresses, they pretend what you want them to be. If you really knew that she loved you the worry would go away yet it is still there. How long does love last anyway? Even if you both had a normal life there is no guarantee it will last a year. With a sex worker (which is what she is, not an escort as you like to pretend) there are so many variables and problems it is unlikely to last six months.
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A
female
reader, anonymous, writes (25 August 2020): There is no such thing as a site that specializes in dealing with the emotional aspects of relationships with sex workers - you would have to consult a reputable life coach and therapist 1 2 1 if you wanted help with this.They would treat it as a relationship issue, and take into account your background and hers.What I do not understand is why you are worried. Most prostitutes do not fall in love or want a boyfriend or lover, you should be over the moon she wants one and has selected you.But you also need to take into account that she could soon get bored, and she meets so many other men that she can easily replace you at the drop of a hat with someone she finds more attractive, better at sex or whatever.Most women who do sex work see sex as a disgusting boring thing they only do for the money. Just as most people who work as accountants all day do not want to be doing book keeping in their spare time.You call her an escort one minute and then a sex worker. They are two different things. A real escort is not a sex worker. She is classier, she is less likely to be having sex with her client and she only spends time with classy, wealthy clients. They do not want her as a blow up doll or for an orgasm. That would be the icing on the cake if it were to be included.A real escort spends a lot of time and money on being her. She would spend more money than most women earn on her home, appearance etc. Many of them have a secretary to arrange their bookings.Some sex workers are young students who struggle with money and realise they would be financially stupid to sleep around with other students for free, so they sell their time to older men who have a paid job. They find the older men have more sex appeal, more confidence and can take them to better places. They promise themselves that when they are ten years older they will stop, but they enjoy it and it pays well so some take it up full time or as well as their normal job later.As for telling you not to engage in open relationships. This is hardly an open relationship if you are her boyfriend and the others are only paying customers. Work is work and love is love,two different things. But you should protect yourself against catching some nasty illness, safe sex.The odds are that she will tire of you when she finds someone more stimulating or who can offer her more so make the most of it while it lasts. She is used to looking upon men as providers and she always will now.She also knows she has so many years to go before she loses her looks and has to make the most of them.She would not bother with a man who cannot provide for her and the men she meets would not want her if she was plain or old.I used to know a lady who was 67 (and very plain) who went out with very young good looking men - despite being married - but she was a bored lady and longed for secret sex. She would give them good sex if they took her to expensive lovely places. They were happy to do that because it was cheaper to date her than to pay a sex worker and she was happy to get away from boring old ugly bald hubby for a bit for a wild time, everyone was happy. Husband never found out. It went wrong when she fell for one of the young men and was nagging him to see her more. She became far too demanding and pushy and he dumped her.
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A
female
reader, anonymous, writes (24 August 2020): You say you would not ask her to give her job up for you. Y You would have to be very rich before she would even consider it if she is a real escort, she earns far more than most men, she won't give up her life and great income just to please you.
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A
female
reader, anonymous, writes (24 August 2020): I have had four clients come to me regularly who were escorts - all of them young and attractive, two of them were real and genuine escorts - that means they were very well educated, spoke numerous languages, articulate, intelligent, lots of common sense, very well dressed in expensive clothes, expensive big house and car, housekeepers, gardeners etc. They spent a lot of money regularly on hair, make up, manicures etc. The sort of men these women "date" are top executives and business owners. These two could easily have turned their back on sex work and run a successful lucrative business that did not involve sex, but they enjoyed it and they were very cautious as to safety etc. They had a fantastic income and lifestyle and were extremely picky about who, when, where etc any sex happened. In fact they were far more fussy and slept with far less men than many women who are easy lays.The other two were dreamers. Both insisted they were escorts. One was a street walker who could barely string a sentence together, swearing, over weight, wearing very cheap charity shop clothes, relying on handouts and stuff from others. One picked up guys in bars and was a bit more high class and selective, more expensive than her. But neither were escorts. A real escort is very expensive and they do not date - why on earth would they? That is like saying that you know a woman who charges a lot to make hand made clothes and she has chosen to spend a lot of time making you clothes for free instead of taking on more clients who pay. Paying for sex or a woman's company goes back to the time of Adam and Eve. There are mentions of it in the Bible. Many women now turn to it because they are desperate for money, nowhere to live, no love in their life or need money for drugs. But a true escort is classy, very classy. She is too level headed and smart for that stuff and it would put off the sort of customers who are happy to pay her a lot of money for her company. Some of her customers will pay her to go with them to the theatre and restaurants or business trips. She is not going to be interested in a meet of just an hour or just sex or sleazy. A true escort would only have rich and powerful men as customers and she would only pick a man who is even more intelligent, successful special and rich than those as her partner/lover/boyfriend. The last thing she would want is a little boy who needs to be educated about women and the ways of the World or who cannot pay his way.
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A
female
reader, Honeypie + ♥, writes (23 August 2020):
 I agree with Code Warrior.
Only thing I can add... is ALWAYS use condoms.
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A
male
reader, anonymous, writes (23 August 2020): To be honest my knowledge on the subject is purely from what I have read in the past. Never had the luxury of hiring one. As far as I know the escort business was started in the sixties and the idea behind it was as the name entails to provide companions for visiting company CEOs and tycoons on short business trips to major cities like London New York and Tokyo.. I think the duties of an escort was limited by the agencies then to accompany the clients to dinners, parties, sightseeing, shopping ..etc. i.e sex and intimacy was not on the menu but obviously the escort agencies had no means of monitoring the escort if she slept with the client for extra pay which she could keep for herself or not. So it is debatable really if an escort sleeps with her clients or not. My advice is really you are a mature person save yourself the anguish of doubt, don't get involved with her emotionally. There is plenty other nice mature women out there who don't work as escorts. On the other hand as I say my knowledge is purely theoretical so I can be wrong.
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