Asking Eric: Ungrateful sibling keeps wanting cash, but there are emotional strings attached

Dear Eric: Over the last 30 some years, I have been very generous with a sibling who has never been in very good financial shape.

I have sensed a certain contempt from her and her family about my generosity. I get a thank you or an acknowledgment maybe half the time.

She is very short-tempered and regularly needles me about things that happened 20 or 30 years ago, snarky comments about stupid little things I did that made her angry.

After many years of letting it go, I find myself very angry about her ungratefulness and her attitude toward me. I have always felt sorry for her and wanted to make her life better but maybe in doing so I've made her feel bad about herself.

We have not spoken in almost a year. I realize the only thing I can control is my own behavior, so I have drastically cut back on the amount of money I give her.

But I hate feeling angry and resentful toward her, and I would love to be able to find a way to move forward and let go of all of this negative emotion. I don't really even know if she is aware that I'm upset.

– Funding Family

Dear Family: Money talks, but it mumbles a lot, so we have to be especially clear in our communications around it. Cutting back on your generosity is fine, but it's not going to get at the root issue and is likely to be misconstrued.

It will help a lot if you can both have a conversation that's focused on the way you feel about each other and about your relationship. You need a place to work through your resentment and she likely does, too.

Before you reach out to her, think about what you actually want. It may be as simple as a thank you. But I suspect it's more complicated than that. Is there a part of you that's hurt by her response to you or her snarky comments? Is there frustration that the money you gave didn't stop the hurt? Ask yourself what would make you feel valued in this relationship.

You write that she may not even know you're upset; that's painful to read because it suggests that she's not extending you the same thought and care that you're extending her.

Sort through your feelings and figure out what's your responsibility to sort through solo and what you can bring to your conversation with her.

Send questions to R. Eric Thomas at or P.O. Box 22474, Philadelphia, PA 19110. Follow him on Instagram and sign up for his weekly newsletter at rericthomas.com .