We’re living in a new and dangerous era of eat and drinking out. For every new dining format that claims the zeitgeist, the question of how—and whom—to tip looms ever larger. What do you do if you’re dining at Del Posto, where at least six different people are assigned to look after you and you alone? Or sitting at the bar at wd~50, where the restaurant’s combined expertise and skill is consolidated into the same guy who’s topping up your water and mixing your drinks? What about a 20-plus-course tasting menu at Brooklyn Fare handed to you directly by the chef?

The very concept of tipping has been slammed a lot lately, with big-deal chefs and restaurants kicking around the idea of doing away with the system altogether. After all, it’s pretty much just us and Canada left, and the reasons most people tip well have nothing to do with how good the service is (women get better tips than men; tell someone your name and they’ll feel guilted into tipping more).

The issue is that in many states, New York included, minimum wage is lower for tipped employees; the Department of Labor factors in a “tip credit” that they calculate will make up the difference, so employers don’t have to pay up. Depending on where you are, your server could be making as little as half the minimum wage, with the expectation that you’re going to make it up to him with your gratutity. For restaurants to do away with tipping altogether, they’d have to cover the increase in costs themselves, passing the buck back on to you in the form of higher prices. In the end you’re forking over roughly the same amount—it’s all about giving you the illusion of control.

Since there’s so much riding on your shoulders, your main goal should be to make sure everyone is making a living and you don’t look like an asshole. Much of this depends on how much you trust the restaurant management to be giving their staff a decent wage, and to be tipping out appropriately. If you’re in a Danny Meyer joint, you can pretty safely assume they’re not running a modern slavery racket out of the kitchen and everyone is being treated fairly. If you’re somewhere where your waiter is drawing smiley faces on tabs, touching your arm desperately whenever you interact, and upselling you at every turn, know that they’re making dirt and you’re their only hope. Don’t give that place your business again – but while you’re there, tip well anyway.

To help you navigate this confusing game, we’ve broken down 15 scenarios that require tipping, from getting your morning coffee to a dinner out with eight of your closest friends, and rounded up a group of professional eaters, writers, drinkers, and servers to drop some real knowledge. Forward this to your grandparents, your boss, and your cousin who just moved here from Michigan who can’t stop complaining about the price of cocktails here. But first, read it yourself to make sure you’re doing it right.

The Expert Panel

Ryan Sutton, Bloomberg New York food critic; founder and editor of The Bad Deal and The Price Hike
Rosie Schaap, Drinks columnist for the New York Times Magazine; bartender; and author of the memoir Drinking With Men
Lizzie Post, author, the Emily Post Institute; great-great-granddaughter of Emily Post (yes, the Emily Post)
Jimmy Carbone, owner, Jimmy’s No. 43, a craft beer bar and restaurant; founder of Food Karma Projects, an organizer of socially conscious food events, including the annual 5Boro picNYC and Pig Island
Tyler Martin, retail operations manager, Roasting Plant Coffee


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