Life Advice



Ask Amy: Hard luck brother begs for funds

Amy Dickinson, Tribune Content Agency on

Medical notebook labeled Diagnosis Substance Abuse, psychiatric mental questionnaire and pills are on table in psychiatrist cabinet or counselor of this issue or problem

Dear Amy: My brother (age 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 the last 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 still manages to get me to donate, claiming necessary medical bills.

He has also 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 transaction is an hour away for me to travel. It enrages me that it keeps happening.

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

When my extended family saw him a few months ago, they all commented on how unwell he looked.

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 also 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 attempted to intervene on behalf of other elderly relatives, and 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 your options.

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


You have been careful about maintaining boundaries, but you should also 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 of them would repay me for their portion of the total.

One of the friends, who is an amateur artist, painted a picture, had it framed, and presented it to me as payment for her inclusion in the activity.

I appreciate the gesture, but money is tight for me, and I expected monetary compensation.

How do I return the artwork and request payment in legal tender, without creating a rift within this 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 do so.

Contact your friend and speak frankly: “Thank you so much for the painting. It was so thoughtful of you to give it to me. I know I mentioned this to everyone, and I really do need to be reimbursed for the cost of the activity. I’m circling back to remind you. Are you able to send me a check?”

Dear Amy: “Daughter-in-law in Training” needs to deal with her demanding mother-in-law by understanding that sometimes even "no" isn't strong enough for persistent demand-makers.

I have switched to "I can't." It communicates a non-negotiable.

This mom of a toddler has the right to put the members of her immediate household first.

If her mother-in-law makes a demand, this daughter-in-law needs to add the words, "I can't" to her vocabulary.

– School Counselor

Dear School Counselor: I agree that “I can’t” is a helpful phrase to have on hand.


(You can email Amy Dickinson at or send a letter to Ask Amy, P.O. Box 194, Freeville, NY 13068. You can also follow her on Twitter @askingamy or Facebook.)

©2023 Amy Dickinson. Distributed by Tribune Content Agency, LLC.




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