THE QUESTION
We have close friends we socialize with frequently. They are quite generous with gifts and when entertaining at their home. They are very comfortable financially. However when we go out together, they are poor tippers. Also, they don't leave money for the coat check, or tip the valet for parking. When we split the bill, it's not a problem as we can be more generous – but when they pay, as they sometimes say it is their turn, it is embarrassing. Should we say something to them or act like it slipped their minds when we tip for them?
THE ANSWER
I've had many jobs in my life. I've been a dishwasher, with waiters all speaking extra-slowly to me, assuming I was thick. I've scraped gum off the bottoms of chairs in movie theatres. I've scooped up manure, both with a shovel and a pitchfork. I've literally broken rocks in the hot sun. (Not because I fought the law and the law won: I was working on a farm.)
But never have I felt more demeaned, downgraded and serf-like than as a waiter – or "server," as it is now styled – in a hoity-toity part of town, where society's doyennes and mavens, tuckered out from shopping, shrugged off their furs and tucked into lunch.
Some were nice. Most treated me neutrally, but kind of as if I were a species of talking dog. And a small percentage seemed actually to take sadistic, schadenfreude-alicious joy in exposing the gulf between their status and mine, knowing if I were to assert my humanity in some small way, all it would take would be a signal from a bejewelled hand to terminate my employment at that establishment.
And then I'd have to hustle, or it wouldn't be long before the locks were changed on the doors of my crummy apartment. My "salary" was a joke, a pittance. The main money I made was in tips, which I counted every day with trembling fingers.
I remember those days well and so to this day I always tip well. Not extravagantly: usually around 20 per cent. Even I don't agree with those (humans or digital machines) who would shame us into believing 25 or 30 per cent is "the new norm."
Of course, only if the person helping me out has been helpful/useful. That is the beauty, indeed the very point of the tip: you can use it to send a message if the person providing you a service has been incompetent, rude or supercilious. But to be "comfortable financially" and be an across-the-board lousy tipper? Not a good look for anyone.
I do think you should say something to your friends. It doesn't have to be confrontational, but not too "jokey" either. I know it's easier said than done, but I say just come out with it – some version of what you said to me.
Maybe use the occasion of them laying down a too-slim tip. Use the "praise sandwich" technique, something along the lines of: "Thank you so much for dinner, you've always been so generous with us. But you should tip 20 per cent for good service. These people depend on tips for their livelihood and we want you to be as well-thought-of by everybody as you are by us."
If for some reason, they refuse, or backslide, I think you are within your rights to "supplement" their offerings, or reach into your pocket to grease the coat-check or valet-parking operatives yourselves.
I would do it openly, not on the sly. Because, as you suggest, it affects how people look at you, too. You are huddled under your friends' umbrella of cheapness. So wherever you go people will be muttering, cursing and wondering what the problem was. (In my city's Chinatown, where I dine out most frequently, they'll run after you openly asking what the problem was if you give a rotten tip: I've seen it many times.)
I suppose there's a chance your friends' feathers will be ruffled, but if you are as close to them as you've suggested, I sincerely doubt it. Usually people can tell when a suggestion, however ticklish and delicate, is well intentioned.
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