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The question

A friend whom I've known for more than 20 years is tight with money. She's always been careful with it, even though she has a great job that pays well. No problem – it's her money right? But I have a slight dilemma with her latest "gift." It was an anniversary present: a box of chocolates that expired a month ago. Should I assume that she didn't check the expiry date before she bought it? Should I e-mail her for the receipt to return the chocolates? Should I just throw them out? I suspect this was a dreaded "re-gift" (I know that in her job she receives such items). The said chocolates are in the refrigerator and await your instructions.

The answer

Hmmm, First World problems much?

Speaking of which, by the time you read this I will, I hope, be doing exactly what in my opinion you should do about The Case of the (Possibly) Re-gifted Chockies: absolutely nothing.

Yes, I can picture me now: wearing shades, gently swaying in a hammock, trying not to splash my margarita, cool breeze gently ruffling my ear-hairs as I turn the pages of a fat thriller … I've never understood people who want to get up to all kinds of energetic activities while on vacation. I'm married to one. Every time we go away she's constantly razzing me to do stuff: "Let's rent some horses and ride around on them!" Or: "Let's learn to surf!" Or: "Let's pack a picnic and check out that waterfall!"

Why, woman, why? Is life not stuffed with enough unavoidable activity? Why do we also have to run around on vaycay doing stuff? Isn't the point of vacation to avoid doing stuff?

By the same token (I know this analogy is a stretch; guess I just wanted to pontificate about vacations), life is full of friction you can't avoid. So why create some where it isn't necessary?

It's true that a box of expired, possibly re-gifted chockies is a lousy present.

Still, it's better than nothing. And nothing is what I expect from the people around me when I celebrate an anniversary. Honestly, I don't even expect anything from my wife any more, after 16 (lovely) years of marriage. Maybe a kiss.

Some friend is going to get me something for our anniversary? Doesn't happen in my world.

Why do anything at all? Sure, you could e-mail her and ask for the receipt. But that'll just lead to friction, anger, nasty cracks – possibly the end of a friendship. Over some sugary confections?

Anyway, say you get your receipt. Who's going to accept the return of expired chocolates?

I understand these chockies could be a "flashpoint" for a larger issue between you and your friend. You say she's "tight"/"careful" with money – a.k.a. cheap. I'm speculating here, but maybe these stale chocolates were part of a pattern? Perhaps you pick up the tab a lot, buy expensive presents, and she doesn't reciprocate.

That can be a problem. I've wrestled with it myself. I was so poor for so long that I had to train myself – bloody well force myself – to pick up tabs and make other similar festive gestures (each one like a knife in my heart) once I started to be able to afford to. It's hard to shake off the habit of pinching pennies – but it's good karma, good PR and good business. People love festive tab-picker-uppers! How to impart such a sense of occasion and generosity to a penny-pinching pal? That's tougher. I'd say your best bet is to lead by example. Next time you go out with her, cover the cheque. Buy her a shirt on the way home! Pick up the tab for the cab! In other words, ostentatiously pay a few times (it'll be good for your soul, if not your pocketbook), and see if it gets her scratching her noodle a little on whether she shouldn't loosen the old purse strings.

If this doesn't work (I admit it could backfire, she could just think "awesome" and let you pay for everything), then maybe it's time to speak up – just choose your moment and your words carefully. It might be tough for her to swallow at first (much like a stale chocolate), but 20 years is a long time, and if a friend of mine were nursing a similar thought, I'd want him or her to spit it out.

With respect to these chocolates, though: I'd just choke 'em down and stay mum. If you can manage that, picture a vaguely human-shaped lump slumped in a hammock with a thriller on its gut tipping a margarita in your direction and "air-cheersing" you for knowing that sometimes the best thing to do is nothing at all.

David Eddie is the author of Damage Control, the book.

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