About ten years ago, my uncle met this woman at his then-current job and they became friends. He lost his job there due to layoffs, and for the following six to eight months he received phone calls from her on a daily basis, sometimes several times a day. Eventually he got another job.
Somewhere along the line, this woman started complaining to him about various problems she was having at his former workplace (where she still worked) and about problems she was having outside of work. This turned into him giving her money to fix her many problems.
They ate out once in a while, but she prevented it from going any further from the start by telling my uncle such stories like how her ex-husband shot her in the leg and kept tabs on her and threatened to harm or kill anyone who got involved with her. She claimed that the government was taking child support out of her paychecks to pay for her son whom she had with her ex-husband, even though the son lived with her and was over 18. Her reasoning was that her ex-husband bribed judges to get this arrangement set up. Early in the relationship she discontinued the dinner engagements because she told him that people at his former job and her ex-husband's spies were always watching them, and he believed it.
Eventually she was unable to pay her mortgage for her house because so much of her paycheck was going to the supposed child support and she had to move into an apartment. Over time he started paying her more and more money to fix different problems she claimed to have, and at some point he started paying her $275 per week to pay for her rent. My uncle has no high school education and only works blue collar jobs, so that's a lot of money.
This continued for several years, and my parents and I knew little about what was going on here. My father and uncle were joint owners of the house my uncle lived in, and my uncle agreed years ago to pay the taxes and upkeep since he was the one using the house, though he neglected it for the woman. One day at local tax season, my father received a big bill from the town concerning delinquent taxes on the house, and he confronted my uncle about it. It came out then that, not only had he had been paying her $275 per week (she claimed to have lost her job because she was communicating with my uncle), he had taken out several loans and maxed out store credit cards to buy things for this woman (groceries, Christmas gifts for her family, etc.), and even bought her a car. My father made arrangements with the town to pay off the delinquent taxes--my uncle would pay my father $100 per week and then my father would bring the $100 to town hall each week to make sure it got paid, or else the town would seize the property.
This didn't solve any problems, however. He still continued to pay her $275 each week for her rent (I think she permitted him to cut back here) and did his best to pay the loans and debts he incurred for her, but with his wages it was difficult to do and he couldn't get extra hours at his job or a second job. He fell further and further behind on his financial obligations, and her requirements for more money in addition to what she took weekly kept growing and growing. He sunk into a depression and it affected his work performance.
He lost his job in 2013 due to poor performance and had his car repossessed, and he couldn't get a job after that. Even still, she was trying to get more and more money out of him, and finally he could no longer pay even a portion of her rent. He decided to retire a year early to collect Social Security, and he pays her out of what he gets from that. She uses guilt on him and told him that she receives threats about being thrown out of her apartment and that she only eats a little flour mixed with water for her meals.
We had my uncle living with us for free for several months, but he was going through our things. We don't trust him enough to know that he won't take anything, though he was eating and drinking us out of house and home. We arranged for him to have his own apartment at a really good price that he could easily afford on his Social Security (assuming he stopped paying the woman), but he refused to hear about it because it was "too big." He refused an offer to fix up the separate garage so he could at least be warm in the winter. My uncle got fed up with our attempts to find a home and now sleeps in a car.
My uncle refuses to go to the senior center and alienated himself from the volunteer fire department. He spends his days walking for miles to collect bottles and cans and tells friends and strangers that we caused his problems. The woman still gets most of his money and gets him to call her privately so no one can know what they talk about. Lately he cuts himself off mid-sentence and simply says "you know?" as if we know what he's saying, so we suspect that his mind is fading. He eats bread and occasionally fast food. He gets angry if anyone tells him to stop paying her.
What can you do about him? It sounds to me like you have tried many ways to help him. I think his behavior is out of your hands. Does he meet the definition of a "vulnerable adult"? Perhaps it would be useful to report his situation to the Adult Protective Services folks. They may not be able to do anything if he is content to live in his car and give his money away, but at least you will have tried one more thing.
If he wants to keep on giving her money, and it sounds like he does, there's nothing you can do about it. You can report her but she's not really doing anything illegal. He's giving her money and she's taking it. There's no law against her being a gold digging scumbag.
Maybe his mind is slipping (you don't say how old he is). But if he's living in his car and still giving this woman money I would look into becoming his POA or gaining guardianship over your uncle if you can afford to get into all of that. You don't really have any control over him or how he chooses to spend his money right now. At least with POA you would have control over his finances but if he's still mostly in control of his faculties he probably won't let you anywhere near his finances.
There may be no solution if he won't accept help. We can't make people accept our help.
My uncle is 66 years old, and the woman definitely exists. A cousin of ours also worked for the same factory as my uncle and the woman around the same time that my uncle was there. This cousin now works at a supermarket where he sees the woman buying expensive food on a regular basis and tries to tell him (the cousin) the same sob stories she tells my uncle. My uncle cannot be convinced that the woman is using him for money at all, or he will get mad and storm out.
My uncle definitely is paying off a lot of debt--but all of it for this woman. When the delinquent taxes came to my father's attention, it came out that my uncle was paying her rent. Later my father found out that he had huge bills with department stores and had told our cousin that he'd bought her a car and was buying Christmas gifts for her and her family. Most days, my uncle has nothing but pocket change and whatever he can scrape up from the bottles and cans he picks up.
My uncle reluctantly pays my parents $100 a week from his Social Security to pay off the delinquent taxes. He also ruined the house he lived in through neglect--again, to have more money to give to the woman. My family is trying to sell the property, but the house needs to be demolished in order to be insured so that it can be put on the market and we need to come up with the money for that. Still, he gives the woman all of the money he can come up with. The woman knows that my uncle will get half of the profit from the sale of the land and pushes him to push my father to get the land sold as quickly as possible, which tells us that she thinks she's going to get the money from him. She's told him that they will only be able to live together once the land is sold because they'll have their own house somewhere (but she won't let him see her at all except when he gives her money).
He gets angry with my father whenever my father offers to help him with his finances. He won't stop paying the woman because he believes that the woman is in real financial trouble and that her eviction from her waterfront apartment is imminent. Yet he refuses to do anything to improve his own situation--it's likely going to be a cold winter and he won't take an affordable apartment. He's enrolled in senior housing, but we wonder whether he will forfeit the apartment when his number comes up.
A prostitute doesn't cost that much, and that's really what he's buying... (or at least to PROMISE of one)...