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Asking Eric: Sibling rivalry results in $20k ‘bill’ to parents

October 16, 2025 by Chicago Tribune

Dear Eric: My husband and I have been married for 40 years. He has two adult sons in their 60s and I have an adult daughter in her 50s. Over the years we have helped one son, who has two children and my daughter, who has one child, while they were going through divorces with large sums of money in order for them to keep their houses. We have contributed to all three grandkids with college 529 funds.

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The other son has never married, has no children, owns his own condo, and has a good-paying job and spends all of it on whatever he fancies. He has a longtime girlfriend who supports herself. She stays with him a day or two a week.

He feels that we should “gift” him the same amount of money that we have given the other two children, which would be more than $20,000.

Financially we could do it, but we are 76 and 87 and are concerned about future health issues or other unanticipated issues that may arise. What should we do?

– Unsure About the Future

Dear Unsure: Your son is trying to treat an emotional quandary as if it’s a ledger that needs balancing. Your generosity to his siblings in times of need has nothing to do with him. But, as siblings are wont to do, it’s not surprising that he’s comparing their lives to his and asking for “fairness.” This isn’t the same as a parent bringing two young children home a tasty treat from a business trip and neglecting a third. And even though it may feel to him like he’s getting the short end of the stick, his feelings are his responsibility. He’s not owed this money. (And it’s not because he can afford to do without it. It’s because it’s not his money. It’s yours!)

What is unfair, and shortsighted, is his request that you give him a sum of money large enough to potentially destabilize your lives should your health decline or you need more extensive care as you age. This stability needs to be the priority. Tell him that you have concerns about the future and, before he can further decide what you’re going to do with your money, tell him that you’re working with a financial adviser and/or estate planner to provide for yourselves and, eventually, for him. And then do actually seek out the advice of a professional for now, for later, and for after you’re gone.

As you make decisions about your estate, you can share that information with your children, if you want. This may help them to manage their expectations and emotions. You can be transparent about your thought process. But if your son is keeping tabs on what checks you’ve written to his siblings, that’s not a problem you are responsible for fixing.

Dear Eric: I recently hired a painter who I’ve hired before. He told me to text him my colors and he collected the paint from the paint store.

I was home while he painted and noticed that the name of the ceiling paint was different from what I asked for, but I understand that names can change. I liked the color, so I didn’t think much about it.

But for the walls of a bedroom, the paint color was clearly wrong, and I hate the look of it now. I didn’t see the final work until it was done.

I asked if this was the color I ordered, and he said yes. I paid off the contract and he left.

Then I went to stow the paint cans in the garage and realized that the ceiling paint and the bedroom wall paint were each wrong. Their codes were one digit off from what I actually wanted. When I asked him about it, he said the paint store gave him the wrong paint and admitted that he didn’t check the cans.

Who’s ultimately at fault here? I feel like I am, since I’m the project owner. But I admit I am rankled at having to eat the cost of having the room repainted as it will likely cost me $500.

Is this just a live and learn situation? The paint store and painter bear no responsibility here? The painter’s contract has no verbiage about liability for errors of any kind.

– Painted Over

Dear Painted Over: He should have checked the product he was receiving before he left the store. The store is “at fault” for giving him the wrong code (if they were the ones who mistyped, and not him). But part of providing good service is making sure that you’ve got the right tools. Sometimes mistakes can’t be painted over but, in this case, they literally can. He should have offered to fix his mistake, if not for free, then for a discount.

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

Filed Under: Fire

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