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The question

I'm about to take a vacation to a developing country with a lady friend. We've travelled together before. She likes to make all the tipping arrangements for our trip. She insists on keeping to the top amounts suggested by the tour companies. She requests we split the tips in half, not waiting to see the service level. As well, she brings gifts for the guides and drivers. She tips generously and steadily to all the service people she encounters. I am obliged to match this. Tips are important, but her gratuities are out of proportion to her own resources. After our last trip, I was getting cranky about the incessant talk of setting up tip envelopes. When I suggested we each do our own tipping, she said if I did not come up with my "half," she would happily make up the difference so the service person got the whole suggested amount. I found that approach insulting to me. David, in the interests of harmony, what are your suggestions for resolution?

The answer

I know the question of tipping in developing countries is tricky.

Especially when you go to one of those "all-inclusive" resorts – you know, where you pay up front, get a plastic wristband and as long as you're wearing it, can swim up to the bar, or sashay to the buffet and have whatever you want without any money changing hands.

Whenever my wife and I travel to one of these, the question of what to tip, when and how often, gnaws at her innards (metaphorically) like a fox in her tunic.

(I'm alluding to the apocryphal story of the Spartan boy who remained silent as a fox hidden in his tunic chewed out his intestines. Difference being: my wife does not remain silent. It concerns her so deeply and is the subject of so much discussion, that it threatens to compromise our holiday fun.)

So, I handle all tipping-related matters. Truth is, I'm not exactly sure how to deal with it, either. There are so many of these non-transactional transactions on a daily basis (I have a hard time resisting free stuff, so I swim up to the bar for their watered-down drinks rather a lot), that if I tipped every time, I'd quickly be cleaned out.

So I fill the pockets of my swimsuit with coins and tip on an instinctual – i.e. sporadic, erratic and capricious – basis.

Also, we always leave something at the end of the week for the hard-working people who clean our room and make the beds. That, too, is a bit fraught, but in the end, we always find a number that seems right.

What I'm trying to say is: I understand it's tough. Not just in developing countries. The whole question of tipping, I think, bothers people more than they let on and here at Damage Control HQ, we get more questions on the topic than you might imagine.

Last one received: "Our friends are wealthy, but they're horrible tippers and that embarrasses us when we got to restaurants. What do we do?" I offered my suggestions (basically: nothing wrong with supplementing/augmenting your miserly friends' tips), which they were, of course, as always, free to take or leave.

No need to tip me! (Though naturally I wouldn't turn one down if offered.)

In your case, though, I beg your pardon and hope this doesn't seem like a cop-out, but I don't see a major problem, here.

I do understand your concern she's overtipping and you feel uncomfortable matching that amount. I don't see why you couldn't have that discussion. Truly, you should be able to set the level of your own tips.

Just say something similar to what you've said to me, i.e. "Hey, I think tipping's important, too. But I don't feel like always tipping the maximum suggested amount."

At which point I bet she'll reiterate her offer "happily" to make up the difference.

You say you're insulted by that. Don't be. Be relieved. The key word is "happily." Doesn't sound like it would bother her at all.

And you say you're worried she's tipping out of proportion to her means. Let's file that under S for: "Something for her to worry about."

I do think it pays to remember, since you are in a "developing" country, that money will probably mean exponentially more to the people receiving it than it will hurt you and your friend to give.

Honestly, in your flip-flops, I'd be thanking my lucky stars. Seems like your friend has put a lot of thought into it. Why not just let her handle that whole side of things, relax and enjoy your pina colada – and the excellent service you'll no doubt get with all your friend's tipping and gifting on behalf of you both – in the sunshine?

Are you in a sticky situation? Send your dilemmas to damage@globeandmail.com. Please keep your submissions to 150 words and include a daytime contact number so we can follow up with any queries.

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