Dear Abby column examines generosity and risk as a retired father helps others while facing housing insecurity

A Dear Abby column published this week spotlights a tension between compassion and financial stability when a retired father with a big heart quietly helps others at the expense of his own finances.

In one Mississippi case, a family member describes a father who has long given away grocery money and loaned the family car to those in need, only to watch his fixed income grow strained. He has started paying rent and groceries for the neighbors upstairs and even covered a car repair, leaving him unable to cover his own rent as a credit card nears max out. The letter asks how to help him without enabling the cycle.

Abby’s guidance in the column recommends consulting an elder-law attorney to determine whether conservatorship could help, and, if possible, for a trusted relative to take on the role to ensure rent and essential expenses are paid. If a family member cannot serve, appointment by a court may be necessary. The aim, the columnist writes, is to protect the father from himself while balancing his generosity with his own needs.

Another letter from the East describes a smaller travel group situation: one member researches and books lodging, with the others paying their shares, and when the writer had to withdraw because of illness, they asked for a refund of roughly $800, which the group refused. The columnist says the writer is not greedy but is being taken advantage of, and suggests practical remedies such as offering the lodging to another traveler or having the group find a substitute so the money can be recouped while the trip proceeds.

Dear Abby, created by Abigail Van Buren (Jeanne Phillips) and originally developed by Pauline Phillips, remains a cultural touchstone for pragmatic advice on personal finances, caregiving, and relationships. The column routinely points readers toward professional guidance—such as elder-law experts—and to establish boundaries that protect both generosity and personal stability.

Distributed across major newspapers and online, the column's approach to sensitive family and financial topics continues to resonate with readers who face similar dilemmas. The current discussions underscore a broader cultural conversation about caring for aging relatives, the limits of charity, and the need for practical solutions.