Dining

Tipping Points

Industry experts share tipping advice for big groups, dates and more
Illustration: Libby VanderPloeg
Tipping points
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It was a most excellent evening, one for the record books. The two (or four, or dozen) of you feasted, clinked glasses, laughed and caroused, and all was right with the world.

Then the check came, and things got weird.

Debate rages on about dropping the practice of tipping altogether in favor of a set service fee to ensure a living wage for restaurant employees. But in the meantime, tipping practices are all over the map. Some people tip on the total before tax, some after. Others might take a pricey bottle of wine out of the equation and just pay a flat amount. That can lead to some serious awkwardness when you're dining out with a date, a group of friends or even your parents from out of town who might not be on the same page about gratuities. Even servers and bartenders who deal with it for a living aren't immune to it when they're off the clock.

Group Gripes
Darron Cardosa has been waiting tables since 1990 and dishing the dirt about his customers for his website, The Bitchy Waiter, since 2008. Though he's dealt with every possible dining scenario at work, he finds himself facing a "phobia" of going out to dinner with a big group of friends, knowing that the party will look to him to figure out what everyone owes.

"They just hand it to me, which I hate. I get really nervous in that situation," he says. In part because he's had to call people out for not leaving enough.

"People just think that they're going to slide under the radar, and if they don't quite leave enough, no one will know who did it. It happens too often," sighs Cardosa, who once confronted a fellow dinner guest about having left only $10 for her $10 margarita, with nothing figured in for tax, gratuity or the birthday girl's meal.

"She said, 'I've got $10, and that's all I'm putting down. My credit card is at its limit.' I'm like, maybe you shouldn't be going out to restaurants."

Solution: Though you can't always account for other folks' financial woes, a little technology might take the emotion and awkwardness out of the equation. Dine armed with Gratuity or one of the many other tipping apps out there and let your phone do the talking for you.

Photo: Dave Katz/Tasting Table 

Tip Snatchers
But though Cardosa could see something and say something right then, he's got to keep his lips zipped when he's on the job. He has never actually caught anyone in the act at the casual Queens restaurant where he works, but he's keenly aware that some diners are in the habit of pulling a fast one on both their friends and the helpless server by slipping back and grabbing a few bills off the table. "I'll know before that there was money there when the whole group left and that one guy was lingering and now there's a little bit less. I guess he just pocketed it," he says.

Solution: Get better friends. Because yikes!

Parental Problems
On the flip side, Cardosa often encounters younger diners eating with their parents—who may not be in touch with contemporary tipping norms—ducking back into the restaurant to add to the cash stack. "They come in acting like they forgot something, and they'll lay five extra dollars on the table, whispering, 'I'm sorry, thank you so much.' Then run back out. That happens plenty of times."

Solution: Perfect your "Gosh, Mom/Dad, you've done so much for me throughout the years, the least I can do is get the tip" speech. (And, really, isn't that true?)

RELATED   Dating Advice from Bartenders »

Cheaters and Cheapskates
Thanks to updated credit card technology that can split the check seamlessly, large groups are tipping a little lighter without the fear of looking like cheapskates in front of their dining companions. "I will get a check split six ways evenly and get different amounts on every single check. I'll even get dollars and cents on one check and then $3 more on another," Katharine Heller, host of the Tell the Bartender podcast, says. "They're doing it privately, and they're not asking each other what they should tip. Back in the day when more people did pay in cash, it was a little bit more public shaming into tipping more."

Solution: Speak up. This professional insight keeps Heller on her toes when she's out with her own friends, and to massage away any potential awkwardness, she finds herself coming up with excuses for throwing down a few extra bucks. "When I go out with my friends and I know that some of them aren't the best tippers, I'll ask, 'So what do you guys want to leave?' or say, 'You know what, I got this. This is more expensive, and I'll tip more.' I'll make an excuse for it, because I don't want to seem like a high roller, which I'm not. It's just the right thing to do."

The Dating Divide
While Heller sees group diners trying to get lost in the shuffle, she notes that on dates these days, they're often trying to stand out.

"I've noticed that newer couples or younger kids tip very well if it seems like a first date. And they always sort of let their date know; they slide it over," she says. "Back in the day, people would hide it, and you didn't look. Now they just leave it open. They want to let their date know how much they spent on them."

Heller, herself, once broke up with a man because he tipped poorly. "He was terrible in general, but that's what I told myself when I broke up with him."

Cardosa agrees with using that as a metric and shares the story of a regular customer who would bring her first dates in to see how they treated the staff. "I guess I don't judge," Cardosa says, "but I do question what their background is. I always just assume that the person who's leaving a little bit more than the other probably has waited tables."

"I always felt like she was giving him this test. I'm certain that if her date was tipping and didn't tip enough, it was probably the end of that," he says.

But if a couple is just plain old having a bad date, Heller is well aware and knows her tip might take a hit. "People get in a fight, and they're like, 'Check!' and they write whatever they can. I'm more worried about them as a person. Are they OK? If that ruins my tip, I don't care as much, because I haven't done anything wrong, and there's nothing I can do to rectify the situation."

Solution: Be generous, even if your date is less than stellar. Heller has a tip if you'd care to return: "If it's under 15 percent—even if you're nice—I definitely judge you the next time you come in." 

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