The fraught art of festive tipping

youHE CHRISTMAS CAROL “Silver Bells”, first recorded by Bing Crosby, more or less nails the festive mood in New York. “City sidewalks, busy sidewalks | Dressed in holiday style,” he croons. “Strings of street lights | Even stop lights blink a bright red and green | As the shoppers rush home with their treasure.” All that’s missing is a lyric about holiday tipping. In the Big Apple, it is not only Father Christmas who is concerned about lists. Many New Yorkers make “tipping lists”—and check them twice.

Festive tips go to those who make New Yorkers’ lives easier. Doormen, dog-walkers, food deliverers, garage attendants, hair stylists, nannies, yoga instructors and the like expect a Christmas gratuity. Trying to figure out who to tip, and by how much, is as much part of the seasonal planning as picking a tree or having Chinese food on Christmas Day.

Tips are given in gratitude for services rendered; if not a formal requirement, in America they are expected. In the festive period it is customary to give a dog-walker the equivalent of a week’s pay. A nanny should get one to two weeks’ worth. Food-delivery workers 20-25% per order. Streeteasy, a property-listing site, suggests tipping FedEx or UPS couriers $20.

Tipping doormen is particularly fraught. Some residents say they consider their doormen to be almost family. They are trusted, discreet, and watch out for the safety of residents, including children. No-one wants to give too little—or too much. “It is all so potentially awkward,” says a stressed-out New Yorker. Elaine Swann, an etiquette expert, suggests that as long as a tip is not given in a crumpled ball, it is likely to be gratefully received. But to avoid awkwardness, she adds, many givers these days use electronic-payment systems, such as Zelle.

Among doormen, at least, cash remains king. Every doorman your correspondent interviewed says that while cookies or poinsettia potted plants are all very well, they always hope for an accompanying envelope of cash. One, manning the entrance of a swanky building on Park Avenue, says that in 2021 festive tips made up a tenth of his annual income from him.

How many doormen get may depend on the type of building. Tenants, on average, are stingier with tips than owner-occupiers. For those who toil in posh buildings along Fifth Avenue, especially senior staff, tips can run into the thousands. “You could get $900 from one resident and $60 from the next-door neighbor,” says a doorman.

Those in luxury apartments overlooking Central Park may be an exception. But most New Yorkers, including bus drivers and teachers, live in buildings where tipping a superintendent or a porter is the norm. During the pandemic, too, appreciation grew for those who showed up to do their jobs when many white-collar workers were able to stay at home. Streeteasy suggests giving a doorman $25 to $150 and maintenance workers $25 to $75. Casey Roberts of Streeteasy says, “It is really just about showing your appreciation.”

Most recipients are grateful for whatever they get. A building manager says one colleague sees them as gifts rather than tips. “He doesn’t open the envelopes right away. He likes to wait and open them all on Christmas Eve.”

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