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Question: When our sister died ten years ago, my brother became the trustee of her five-year-old daughter’s trust. Drew invested Mandy’s money in a business he was starting, and Mandy received stock in return. The business folded this year, and now the stock is worthless. Shouldn’t Drew repay our niece the money he lost? He says what happened is nobody’s fault.

Answer: That’s just the way the investment cookie crumbles, is MORE

Q: My fiancé, Alan, recently had a heart attack. If we go ahead with the wedding, he will be covered by my health insurance (he has none), but I’ll become liable for all his current medical bills. What should I do?

A: Like Humphrey Bogart in Casablanca, you’ve been misinformed. Individuals are not legally liable for debts their spouses incurred before they were married. As a practical matter, though, those MORE

Question: Is there anything wrong with asking a good friend to secure the loan I’m giving him with the title to his car? Tom really needs the money, but he can be pretty irresponsible, and I don’t want my $2,500 to become a gift.

Answer: In a word, No. And in two words, Absolutely Not.

Lending a flakey friend that kind of dough is a very generous thing to do, and MORE

Q: My parents were always careful with money. But since Mom died, Dad has taken up with a much wealthier widow and is blowing through his savings entertaining her. Isn’t she wrong to let him undermine his financial security like that?

A: Maybe. The key question: Is your dad’s lady friend in the dark as to his resources or is she just uncaring? If your father has been pretending to MORE

Question: A friend gave me a subscription to a magazine I don’t care for. When I canceled after one issue, the magazine sent the refund to Gretchen. I don’t want to seem small, but especially since I’d given her a nice present, shouldn’t Gretchen have given that money —- or another gift —- to me?

Answer: Call us unsentimental, but gift-giving is a transaction as well as a pleasure. And, usually, MORE