Guidance For The Perplexed

Have a friend (former client) who recently started living with a lady who left the SP business to be with him. He is in his mid fifties and he is a successful equity and fixed income trader who is rolling in money. The lady is in her mid thirties.
She is not only attractive but has a great personality. She is a master of the GFE, so much so that in her 14 year career a number of clients have made fools of themselves falling head over heels in love with her. The agency actually had to call the cops about a guy, a successful lawyer, who began stalking her. Oddly, another guy was desperate to have a child with her and had a contract drawn up offering very generous and guaranteed support payments. She declined.
Anyway to be with her my friend moved from Toronto and started working in his firm's Montreal trading room. He bought a big apartment in a golden square mile landmark building on Sherbrooke. They have lived together now for about eight months. He makes her whole for lost revenue and she benefits from his higher end lifestyle. She claims to be happy.
Before taking the plunge he asked my advice. One of the nice things about this and other adult boards is that they sometimes contain a wealth of information on local working girls, including the lady in question. Something I noticed was a merbite's comment in a review where she told him that she left one work location for another because the clients in the place she left were older and therefore "too soft". She wanted younger and harder guys. So I told him to watch out because she might have trouble transitioning to a one on one "civilian" relationship. The risk was that she might miss having great sex with mutiple partners just to hang with him.
Sure enuf she has recently asked if he would mind terribly if she went back to work one day a week. He is not keen on the idea but has asked again for my advice and I know she's got a hold on him.
Any ideas on what I might say to him?

To answer Patron, they are not married. He says that in Quebec unlike the other provinces people living together remain separate as to property. Is he correct? Idk.

I think I agree. This lady always said that she was in the biz just for the money and maybe that influenced his decision to take up with her, but I always got the impression that there was more to it than that. I'm sure she would not even have started if the money was not much better than other jobs she might do, but the personal freedom she had working when she wanted to, not having a boss etc and having a good income I think all equally appealed to her. I saw her a few times myself back in the days and my impression was that she really enjoyed giving pleasure. That seemed to be very important to her and I doubt that securing a good client base was the only reason. I'm not a psychologist but possibly she has a strong need to feel loved and appreciated. Possible? Idk. I had no chemistry with her myself but you could see that she was trying everything in her bag of tricks and was genuinely disappointed and puzzled that she couldn't figure me out. I also suspect that she likes sex alot (tho I was unable to do much for her myself), and at 35ish she is experiencing the peek of female sexual desire whereas Alan has probably been on the decline for decades.
While the encounters are limited in duration and scope, when they are successful they offer some of the best that male/female relations have to offer and without the traumas, difficulties and unhappiness that can also accompany "normal" relationships. I think for her it was very rewarding to be able to experience that good part with her clients and that is what she probably most liked about her job because she would not now be going back to it just for the money, they have plenty.
Oh almost forgot to mention, she is a serious person and a mature adult, not at all a party girl or into drugs or anything like that. But I think she misses her friends in the biz a lot, both clients and co-workers.

I thought about that. I'm pretty sure that she does not read the different boards. On the other hand I suspect that at least some of her (former) clients do since as mentioned she has been reviewed from time to time here and on two other sites since 2004 to my knowledge.

I don't think he has provided for her cradle to grave but he says that he has fully covered her foregone revenues. That money belongs to her. He also gave her one of his cars, a new six cylinder Audi sport. They took an expensive trip last March and of course he paid everything. He can afford it. These guys work mostly for bonus. I don't know what his bonus is but for sure it is seven figures per annum. I don't think she is worried about money. Working occasionally is not going to make a big difference.

Patron you are obviously an experienced guy. She is mid thirties but looks maybe 28 (she is Asian). She was an athlete back in China and I'm sure her body is the same as it was when she started working (I said 14 years but on reflection probably 13 years ago) because it cant look any better. But you are right. She has said more than once that she worries alot what will happen as she grows older.
She is university trained but her credentials were not recognized here in Quebec. One reason she needed money.

Thanks for the comments. I told my friend to continue in this relationship only if at the end of the day he was completely comfortable with the lady seeing other gentlemen from time to time. Maybe he doesn't care. I remember him saying that her having been a naughty girl actually enhanced her appeal to him.
On the other hand if he was expecting her to change going forward I said he should end it. As someone said you can't turn a whore into a housewife. Some escorts don't really like the life but others thrive on the sex and the social interaction with clients and coworkers. After screwing thousands of guys, many of them probably good in the sack, I have a hard time seeing her settling for a middle age man whose libido is probably on the decline, especially now that she is at her peak. In her case its even more problemmatic because its not just receiving pleasure that she enjoys but giving it also is very important to her. Her intimacy with clients is genuine and thats what makes her a great SW. So he would have to accept not only her getting laid when he's not up to it but sharing herself with others emotionally in a way no different than with him (though she would dispute that because she insists that her relationship with him is not the same in terms of involvement even with her best long standing clients). Thats a tall order imo. I suspect 13 or 14 years in the business has an influence on how you think and who you are, same as any profession does.