Dear Amy: Twenty-plus years ago my older sister lent me $3,000 at a time when I was struggling to make ends meet. I promised to repay the loan before the end of that year. The time came, and I wrote my sister a check for the full amount but she did not cash it, saying she did not need the money and that the loan was forgiven.
Fast-forward 20 years. While my sister has remained financially stable for the duration, I am now in a better place financially, due to a family member leaving me some money recently.
After learning of the inheritance, my sister asked me for the money back.
I can afford it and so I plan to repay it, but I can't get over her surprising request. Might you offer any words of wisdom for this unsettling sibling situation, which has added stress to our already-distant relationship?
— Lucky sister
Dear Sister: My perspective is that you should happily, gratefully and graciously write your sister a check, keeping in mind her generosity when you needed it.
I know, I know — it's tacky to appear 20 years after the fact and basically expect repayment for a loan that was "forgiven," but hey, you've had this money for two decades, interest-free. If you didn't have extra money now she would not have asked for it.
Your sister "forgave" this loan. Now you should forgive her this fumble, and do so with a generous and grateful spirit. If you can muster the courage to be the "bigger" sister at this point, you'll feel better about yourself and your older sister — and this will be good for your relationship.
Dear Amy: My teenage daughter is invited to a friend's rite of passage. In addition to any gifts for the girl, the hosting family is asking for a donation to their favorite charity — and they are requesting cash or checks made out to them (the family) for this.
We feel the family has good intentions, but besides getting good "karma" for this gesture, they might also stand to benefit from a sizable tax deduction — and that rankles a bit.
Wouldn't it have been a nicer thing to have said, "We're collecting checks made out to such and such a charity, and here's the information"?
I'm happy to donate, but am I a bad guy to think this is a bit much?
— Gary the giver
Dear Gary: I agree with you — I would not want to send a check made out to the family unless I wanted to make a donation to the family.
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