Dear Eric >> My youngest daughter, a pediatrician, got a divorce two years ago (her husband had been taking money from her practice and not telling her). Her mother and I divorced 40 years ago and are on good terms. For whatever reason, my present wife and I almost never saw her or her kids. There was no falling out or other reason for her not to have anything to do with us, including Christmas, the kids’ birthdays or special events they might be in.

During the divorce, she got into financial problems, and we supported her to the tune of more than $50,000. She told us things were going to change and she would start having more to do with us. It has been 10 months, and we have heard nothing from her as far as paying back the money or anything else. So, I am not sure where to go with this as that money was a significant part of our retirement. Her mother is not in a position to help her.

— Loan Danger

Dear Loan >> I hope that you and your daughter drew up a loan agreement or other kind of document that set out the terms of the loan and the desired schedule for repayment — or even just the understanding that this is a loan and not a gift. Documents of this sort can be awkward with family, but with the amount of money you’re talking about, it’s better to feel briefly awkward than to end up resentful because of dire financial straits.

Even if you don’t have anything on paper, it’s time to have two separate conversations about your relationship and expectations. Money first. Ask her what her plan is for paying the money back. Explain how it impacts you and get a realistic schedule from her. If she’s still not financially secure enough to make even small payments, you need to know that so that you can plan accordingly.

Then, have a relationship talk. Ask her if her promise to change was genuine or, if not, what her reasons for being estranged from you are. I’m not very comfortable with the idea of your daughter having nothing to do with you (for years?) but gladly taking $50,000.

Dear Eric >> I wanted to thank you for your response to my letter — Obligatory Guest. You are correct in your assessment that they probably find me a little annoying and appreciated “hearing” it from someone outside of things. The brides did indeed find a strange (and cruel) way of showing it. As a follow-up, I’d like to share that one of the brides seems to have realized the damage that they did. She has since attempted to repair the relationship with me and with another person in the group whom she treated similarly. I am very happy to see that she realized how cruel she was, and I’m happy to give her another chance.

— Obligatory Guest No More

Dear Guest >> Thank you for the update! I appreciate it! You’re being very generous to your friend. I hope they earn that generosity. You deserve good friends!

Send questions to R. Eric Thomas at eric@askingeric.com.