Boundaries to aid brother

My brother, 60, has had a difficult life. He has been fired over a dozen times from various jobs.

I also believe that he has substance abuse problems.

A couple of years ago, he moved and said that he wanted to get his life in order.

I gave him some money then, but now it seems he is up to his old behaviors. He’s been out of work for a year.

He frequently “borrows” money from elderly relatives. When I tried to put a stop to this, he told me that he completely understood why my husband divorced me, and the begging (successfully) continued.

Now that my elderly relatives are no longer in the position to give him money, he is back to asking me. I generally refuse, but he manages to get me to donate, claiming necessary medical bills.

He has asked me to be the go-between to transfer money from my father’s account to his because my father is no longer able to physically go to the bank. (My father is competent and agrees to give the money.) This bank is an hour away for me.

I usually don’t answer my brother’s calls, but I am always worried that he will have an urgent need.

How can I maintain boundaries (and keep my money) while making sure that he is OK?

Not My Monkeys

Dear Not My Monkeys:

If you are willing to contribute when you’re asked to pay medical bills, you should ask your brother to show you the actual bills, confirm them with the physician’s office and pay them directly.

You might help by connecting him with local services and with a social worker who could help him to apply for affordable housing or other eligible programs.

You have tried to intervene on behalf of other elderly relatives; you should do the same for your father. You should talk with him about your brother’s requests, and if your dad is competent, willing and able to fulfill these requests, you could help him by visiting his bank and exploring options.

You and your father might want to open a joint account for this purpose, with both of you having access to it. You could link your brother’s account to it and make these transfers online. This would make your participation easier, and enable you to monitor the spending.

You have been careful about maintaining boundaries, but understand that you will not always be able to control the outcome.

Your brother may not be OK. If you understand and accept the likelihood that he will careen from crisis to crisis, you might better be able to pace yourself.

Dear Amy:

I recently arranged and paid for an activity for a small group of friends with the clear understanding that each would repay me for their portion.

One of the friends, an amateur artist, painted a picture, had it framed and presented it to me as payment.

I appreciate the gesture, but money is tight for me.

How do I return the artwork and request payment in legal tender, without creating a rift in the friendship?

In Need

Dear In Need: I don’t think it’s necessary to return the painting, although — depending on your friend’s reaction — you could offer to.

Tell your friend frankly: “Thank you so much for the painting. It was so thoughtful. I know I mentioned this to everyone — I really do need to be reimbursed for the cost of the activity. Can you send me a check?”