Dear Abby: Boundaries on generosity and refunds in two reader dilemmas

A Dear Abby column this week tackles two reader dilemmas that center on generosity, boundaries and fairness in personal finances and shared travel experiences. In one letter, a retired father with a big heart repeatedly gives money to people in need, risking his own housing and finances. In the other, a small circle of women who travel together confront a refund dispute after one member falls ill and cannot make a planned trip.

The first case centers on a Mississippi reader whose father has long given freely to others, often at his own expense. The father helped neighbors upstairs with rent and groceries and even covered a car repair, all while living on a fixed income. His daughter reports that after years of generosity, his own finances are strained: a maxed-out credit card and a looming risk that paying others will cause him to lose his apartment. She asks how to intervene without crushing his impulse to help and without erasing his independence. Abby Van Buren, whose real name is Jeanne Phillips, responds that the stakes are practical as well as emotional and that the family may need outside help to safeguard the father’s basics.

Abby’s guidance emphasizes the potential benefit of involving elder-law expertise to determine whether conservatorship or another form of protective arrangement is appropriate. The column notes that if a daughter can take on the role of managing her father’s finances and housing needs, that would be ideal; if not, a court-appointed guardian or conservator may be required. The central aim is to ensure that rent, utilities and basic necessities are covered while still honoring the father’s autonomy as much as possible. In essence, Abby argues that leaving the father to make financially risky decisions on his own is untenable when those decisions threaten his housing and daily stability.

The second letter concerns a travel scenario. A tight-knit group of women who have traveled internationally together relies on one member to search for and book accommodations, while each traveler covers her own flights. When one participant had to withdraw due to illness three months before a trip, she sought refunds totaling about $800 for lodging and a car rental that could no longer be used. The rest of the group declined to reimburse those costs, arguing that the expenses had become theirs by default. The writer asks if she is being greedy for wanting her money back.

Abby responds that the writer is not greedy and that the situation reflects being taken advantage of. She suggests that if possible, the writer consider not traveling with this particular group again. To salvage the situation financially, Abby proposes a practical solution: if someone among the group has travel interest and money to spare, the writer could offer their lodging reservation as a substitute, allowing the funds to be recouped while preserving the rest of the trip for others. The emphasis is on setting clear expectations and protecting one’s own finances without shaming or punitive sentiment toward the others.

Taken together, the two letters illustrate how Dear Abby frames practical boundaries as acts of care—both for vulnerable individuals who may be harmed by well-meaning generosity and for friends who navigate the complexities of shared plans and refunds. The column’s advice aligns with a broader public conversation about elder financial safety, personal autonomy, and fair arrangements in group activities. The guidance also underscores the value of consulting professionals when complications arise, whether that means elder-law counsel to assess guardianship options or clear, written policies for group travel contributions and refunds.

The syndicated column, authored by Abigail Van Buren and attributed to Jeanne Phillips, is widely consulted for family-finance and interpersonal guidance. In this installment, readers are reminded that generosity can be a strength when balanced with safeguards that protect both the giver and the recipient. For those facing similar situations, Abby’s approach is to prioritize basic needs, establish boundaries, and seek practical remedies—whether through legal channels, renegotiated arrangements, or substitute arrangements that preserve everyone’s dignity and financial health. Readers interested in more guidance can visit Dear Abby’s site for additional columns and resources on elder care, budgeting, and group travel etiquette.