Our Adult Son Has Made Some Baffling Life Decisions. The Result Is That He’s Broke in His 50s.

Pay Dirt Photo illustration by Slate. Photo by Jacob Wackerhausen /iStock/Getty Images Plus. Pay Dirt is Slate’s money advice column. Have a question? Send it to Kristin and Ilyce here. (It’s anonymous!) Dear Pay Dirt, My wife and I are in our early 70s and haven’t updated our will in about 15 years. It’s a good time to update, now that all of our grandchildren are adults, but the concern is our eldest son, “Ben.” He is in his early 50s and in a bad financial place. He’s done it to himself, but we don’t know why. Ben is married to “Terri,” his wife of 25 years, but he does not live with her. He moved out after a few years of marriage and started living with “Jane.” For the last 22 years, he has basically been paying for two households, including mortgage, taxes, insurance, and repairs for Terri, and rent, utilities, food, and other living expenses for Jane. Both Terri and Jane work part-time jobs only. Our son is perpetually broke. We have repeatedly asked him why he is paying for a house he doesn’t live in, and why he doesn’t get a divorce and sell the house. He doesn’t belong to any religion that forbids divorce, and neither does Terri (as far as we know.). He only says, “It’s complicated,” with no further explanation. We don’t know how to handle his share of the estate. We are afraid that when we pass, if he is still legally married to Terri, and she decides to finally divorce him, she will get half. We could also see Jane going on a spending spree with the money. In either case, our son will still be broke. The only idea we have is to put his share in a trust and have one of his sisters manage it, only paying out a set amount every year or only paying approved expenses. The problem with that is he already has a strained relationship with his sisters (basically because they are much better off financially than he is), and this would cause even more issues. Other ideas? —Worried Dear Worried, Let me start by reassuring you that if you use a well-designed trust, you’ll be able to avoid having your son’s wife directly access these funds. But you won’t be able to stop him from sharing the windfall with her or Jane or anyone else he chooses to share it with. Before you sit down with Ben and tell him you’re revising your estate plan, pay a visit to your attorney and discuss how to set up trusts for each of your children (and grandchildren, if you choose) and how to make sure your grandchildren will inherit the remainder of the trusts, no matter what happens to their parents. Also, since your son doesn’t appear to have any children, you should discuss what happens to his trust after he passes away. You might want the remainder of the trust to be split into the other grandchildren’s trusts or you might want the money to go to the charity of your choice. Finally, if you think making one of your daughters the trustee for your son’s trust will make their relationship worse, you should name a different trustee and successor trustee. It sounds as though your son’s life is complicated enough. Having one of his sisters stand guard, distributing your money to him, might infantilize and will likely infuriate him. (And it wouldn’t be fun for her, either.) —Ilyce Classic Prudie An acquaintance of mine recently had a beautiful baby boy. I was happy for her until I learned that she was telling people that I’m the father of the baby. Word spreads fast in our small town, and people are starting to judge me for abandoning this woman and her child, even if she hasn’t said or demanded anything directly from me. But me being the father is impossible. Never miss new Slate Advice columns Get the latest from Prudie and our columnists in your inbox each weekday, plus special bonus letters on Saturdays. Advice Family Personal Finance