Annie's Mailbox

Ask Amy column

Q. For my 50th birthday my parents are going to give me a large sum of money. I have a passion for Indian food, culture, history, and art and have dreamed of visiting India. I have looked into tours before and I know I would need almost exactly the amount my parents are planning to give me.

I am a librarian (divorced) and my retirement fund is less than half of what it will need to be when I retire. I have always been careful with money because I have never had much of it.


Part of me feels I should save this cash and spend it as needed on the various car repairs and other problems that will inevitably surface in the future. But another part of me feels it is time to spend money on something I want, and do it before my health slows me down.

While they’ve said the money is mine to use as I wish, my parents won’t approve of my traveling to India. I am not sure I can enjoy the trip knowing I am spending their carefully saved money on something so selfish.

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Part of me is terrified of blowing this money and all of my carefully saved vacation days all at once. My college-age children aren’t around much and my ex is getting married in a few months to a young blonde.

This is my chance to do something just for me, but I am not convinced I will enjoy it enough. How do I decide?


A. I say go. But only go if you can determine that this is right for you and truly affordable. Part of that equation is whether you can really afford not to go. It is not selfish to choose an adventure that could expand your world and change your life in untold and positive ways, but it is foolhardy to mortgage your future financial stability.


You sound risk-averse by nature. There is absolutely nothing wrong with being careful (in fact, you make the most rational argument for caution), but the fullness of life is revealed in the vibrant colors of new experiences, and no place is quite as vibrant and sensory as India. For further inspiration, watch the British film “The Best Exotic Marigold Hotel.”

Q. I have a wonderful, usually responsible 13-year-old son. He gets straight A’s and is fun to be around. Less than one month ago, he got his braces off and he now needs to wear retainers. The dentist told him that the retainers belong in his mouth or in the protective case.

Recently we found one retainer on his nightstand, where it was not in the protective case. The second retainer is nowhere to be found. It costs $250 to replace it. My son has shown little remorse over this, despite my explanation that he should have had the retainer in the case.

I would like him to bear some financial responsibility toward replacing it. He has about $175 in the bank and generally does not have access to ways to earn large sums of money. I can easily afford to replace it, but I do not believe that doing that would teach him anything.



A. Every single thing you relate is to be expected — including your son’s lack of remorse over the loss of his retainer. He doesn’t feel bad about losing it because he likely never wanted to have it in the first place.

You should show him how much the replacement retainer costs and tell him he’ll have to cover half. If he loses it again, he’ll have to finance the full replacement cost the old-fashioned way — by working it off.

Send questions by e-mail to or by mail to Ask Amy, Chicago Tribune, TT500, 435 North Michigan Ave., Chicago, IL 60611.
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