What can I do about my Grandmother's (83) 'boyfriend' (65) who requests money from her?

She sends him whatever he wants.

My Grandmother has $1,000 per month to live on. In 2010 I bailed out my Grandmother, after she had overdrawn her account by $750. We had an arrangement that I would keep her checkbook, and all the checks / ATM cards in my possession. I would visit her during the first week of the month. We would hang out, and pay her bills. I would give her a check for cash, which she could spend any way she needed. Mid-month, we would visit again, and she would receive another check for cash, and be able to spend it anyway she saw fit. This was working until, she met a man (20 years her junior).

After keeping her checkbook for about 18 months, without any trouble, Grandma decided that she needed all her cash upfront at the beginning of the month. Due to our past experiences I knew this was not a good idea. She was of sound mind, and decided that she wanted her checkbook back, and she was going to marry this man. I did not have a POA or any document saying she could not take care of herself, so I gave her checkbook back, after a strongly worded, matter of fact, discussion.

A couple months later she married this man, at the courthouse without any family present, (odd because she has always gone to church). Over the course of a couple years, they moved 4 times. During their marriage, he had her get rid of of the items she brought to the marriage, pots & pans, nick knacks, her pictures of family were stored away. I had to step in several times to "help" with financial or physical needs. Why me, the grand daughter, and not her children? Easy explanation..I am the eldest grandchild, and have a relationship with her that the children do not. I let her live her life, but watch over her to make sure she does not get hurt, used, or taken advantage of. Her children were over the top, and wanted control of her life. Which most children feel the need to do.

Well after about 2 years, this man decided that he had to leave my grandmother, and moved out of state, without telling her. They stayed married, for several months. He finally agreed to a divorce and their marriage was then ended. While he was living in this other state, I helped Grandma with her finances, and whatever she needed. After the divorce, they started talking on the phone again. He apologized for how he had treated her. He said that the people in his area were helping him to be a better person. Yadda yadda yadda, she started sending him money.

Jump to late 2015. Still in two different states, he made promises of marriage and moving her to be with him. This fell through, as he said it would be too expensive for them to live in his area, on their income. He told her he was going to move back here, so they could be together, and remarry.

The date is approaching for him to return. He requested money for help in getting moved back. Remember earlier I said she lives on about $1,000 per month? Well, I found out in the second week of March, that she was over drawn again. In my gut, I knew that she had sent this man money, the only question was, how much. We went shopping and I looked at her checkbook. She had sent him $1,300 at the first of the month, so he could pay for his way to move back. (or so he says) She is overdrawn by hundreds of dollars again. I will help her, but I need advice. He requests her money, and she sends it to him, with the promise that he is helping her live a better life, and Love.

Where do I go, what do I do? I have her checkbook for the moment, because I said we needed to go to the bank to figure this out, and I did not want her writing any further checks until we get there. She agreed this was a good decision. I am very concerned about her emotional needs, as he keeps "yanking her heart strings". I am also concerned about her living expenses. Her rent check was returned to the landlord, and she has no money for the rest of the month. Don't get me wrong, I will help her out and make sure she has what she needs, however I do not even know where to start with this man. He has an emotional tie on her and can manipulate her to do whatever he wants her to do. I need pointed in a direction to help me, help her. Any thoughts?