Readers' Awkward Money Questions

Authors of a new book explain how to deal with casino winnings, aging parents, and dating.

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After explaining how to deal with requests for money from family members and other financially awkward situations, Jeanne Fleming and Leonard Schwarz took on a new challenge: answering questions from U.S. News readers. The authors of Isn't It Their Turn to Pick Up the Check? were asked how to deal with casino winnings, child support, and alumni donations. A copy of their book went to—drumroll, please—the Alpha Consumer reader who asked how to deal with a sibling who was shunning his financial responsibility to his aging parents. Here are readers' questions and Fleming and Schwarz's answers:

• Casino winnings. Friends recently visited with us at our home in Las Vegas. After a night of gambling (and an unlucky streak), our friends ran out of money. As we were leaving the casino, they borrowed $10 from me to take a last fling on a slot machine. They immediately won a $15,000 jackpot. Following this windfall, they didn't offer to share the jackpot or even repay the $10 I gave them. Am I wrong in expecting a share of the winnings, since they never would have won the money without my loan?

Fleming and Schwarz: Your friends owe you 10 bucks and one absolutely wonderful treat — say, dinner at the priciest restaurant in town followed by great seats at a premium show. Your loan made their good fortune possible, and they should show their appreciation by spoiling you rotten. But a loan's a loan, not an investment. Even if your friends had lost, they needed to repay your loan, whether it was by giving you 10 bucks, buying you a drink or two at the casino bar, or picking up some other tab that would even the score. So since you weren't on the line to lose $10, why should you get a share of the winnings? That would be the best bet in Vegas: You win, I win; you lose, I get my money back.

• Child support. What does the father, who is already paying out a sizable chunk of child support every month say to a child who comes to him for everything that the child support should be paying for, such as shoes, clothes, and school trips?

Fleming and Schwarz: What you say to the child is easy: "I give your mother money to buy those things for you. I'll talk to her and find out what the problem is." It's the next step that's harder: talking to your ex-wife—promptly—and determining whether she's playing fast and loose with your child support payments or your child is hitting you up for things your ex-wife has, for good reason, said no to. Once you find out, you need to deal firmly with whoever is cheating on the deal. And you also need to be careful not to inadvertently punish your child if it's your ex who's behaving badly. If she is the villain of the piece, buy your kid the shoes and clothes he needs—don't make him go barefoot in order to teach his mother a lesson.

• Alumni donations. After a couple of good years during which I bought a very expensive house and new car, I had some tough financial times and am still struggling. Recently, an old college friend phoned me to ask if I would consider a substantial contribution to our alma mater — he suggested $5,000, and I answered that that was way beyond my means. It was a difficult conversation for me, and we haven't spoken since. I am afraid that he didn't believe me and thinks that my $50 gifts mock a cause that's important to him. Is there anything I can do to straighten things out so that he understands that I am supporting his cause in line with my reduced income?

Fleming and Schwarz: Difficult conversation for you? It's your friend who should be embarrassed for presuming to tell you how you should be giving your money away. We fear your self-consciousness about the reason for your modest gifts has led you to lose sight of something fundamental, namely: What institutions you choose to support and how much you choose to give to them are entirely a personal matter. Your friend has no business judging your contributions, if that, in fact, is the reason for his silence.

If this is a relationship that matters to you, we encourage you to tell your buddy that you appreciate his friendship, that you appreciate and share his commitment to your alma mater, and that you'd appreciate it if, as a friend, he would not presume to pass judgment on how much you give to Old Ivy or any other institution. If his response is anything less than apologetic (or insistent that you misunderstood), you might remind him that there are plenty of schools in Africa, battered women's shelters, and spay-and-neuter clinics that he could do a lot more to support. Then assure him that your warm regard for him is not contingent upon the scale of his contributions to any of these worthwhile organizations.

• Aging parents. Our elderly parents have used up their savings and retirement funds and are in financial trouble. They need at least $2,000 per month over and above their Social Security to survive and go to an occasional movie. About $1,000 per month goes to doctors and medicines. I am trying to get my two siblings to agree to each give them $800 per month. My sister and I can afford this, with some struggle. Our brother, however, claims he cannot afford to give them anything, not even $100 per month. Although we are not aware of his real financial situation (he drives two Lexus cars and has a boat), we are stunned and very upset by his refusal. What can we say or do to make him help?

Fleming and Schwarz: Our bet is that back when your brother was a kid playing with Legos, he wasn't known for his selflessness and sense of responsibility either. Unfortunately, even if he can well afford to help but simply chooses not to, there isn't much you can do to make this deadbeat contribute. But what you can do is refuse to allow him to benefit from his disregard for his parents' welfare. Start by not covering up for him. Make it clear to your parents that only you and your sister are helping them. Maybe this will shame your brother into contributing. But even if it doesn't, at least he won't be the undeserving recipient of their gratitude. What you can also do is lend your parents that money instead of giving it to them. That way, if there's anything left in their estate when they die, you and your sister will have to be repaid in full before a dime is distributed to your brother. Finally, we think you and your sister ought to consider shunning this guy. Someone who leaves you holding the bag in this kind of situation doesn't deserve a seat at the holiday table — or a place in your family.

• Dating. What's the rule about who pays while you're dating? I'm still a graduate student, so my disposable income is almost nonexistent. However, my significant other has a steady job and a reliable source of income. I feel guilty that he always pays, even when I do have some cash available. I offer to pay, but he more often than not refuses the very notion.

Fleming and Schwarz: There's certainly no rule of dating that says the person with the most money is always obligated to pick up the tab. Each couple works this out for themselves, based on factors such as how long they've been seeing each other, how independent the person with less money prefers to be, and how much the person with more wants to treat them to things beyond the budget of the other.

That said, you might want to keep this in mind: As tempting as it may be to accept the generosity of someone who enjoys spending his money on you, it's also important to remain the peer of the person you're dating. Unless you want your relationship to be a throwback to the 1950s paradigm of big, strong man looks after weak, dependent woman, you need to do more than reach for your wallet occasionally. You need to actually take out some money and use it. In other words, don't offer to pay—insist. Trust us: Your significant other will not take offense.