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What makes a diner tip $10,000? Servers spill their secrets.

Server Andrea Jackson at Annabelle restaurant in Washington says some customers “give back financially what they've been given emotionally.” (Deb Lindsey/for The Washington Post)
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Michael Zarella told his staff at the Stumble Inn Bar and Grill in Londonderry, N.H., not to get too excited about a tip a customer left on a bill for less than $40 last June. The restaurateur wanted to make sure the sum was released by the bank before divvying up the unusual gratuity.

The anonymous diner, whom Zarella described to Fox News as an “average Joe,” ate a couple chili dogs and some pickle chips, which he washed back with a Coke, a beer and a shot of tequila. Then “Joe” tipped like a mogul: $16,000 was ultimately split by eight bartenders and kitchen staff on duty that summer day.

“Everybody thought it might be a celebrity that was here, but it wasn’t,” Zarella told Fox News. “He gave the money and doesn’t want any PR out of it.” When the operator tried to comp the patron’s meal, he declined.

An Arkansas waitress served a party that tipped $4,400. It led to her getting fired.

Feel-good stories about outsize generosity are catnip during the holiday season. Earlier this month, a waitress in Arkansas got a tip for $4,400 from a party of 32 diners, a gratuity she was required by her employer to share with the entire restaurant staff. Ryan Brandt was (bah humbug!) fired by Oven & Tap in Bentonville for telling her benefactor she couldn’t keep the full amount but (oh joy!) ended up getting $8,700 from a GoFundMe campaign started by the same fan. In a sign of the times, she was quickly hired by another restaurant.

“It’s an early Christmas!” Bhaskar Sundriyal, 37, says about the $1,250 gratuity he received this month from a party of 10 at Rasika in Washington. He knew the 40 percent gratuity wasn’t a mistake, because the person signing the check was a regular and wrote “THANK YOU” at the bottom.

Seasonal goodwill and an ongoing pandemic explain some grand gestures, but not all. “This happens a lot” to him, says the waiter, a native of New Delhi who put himself through school at Howard University and graduated a year ago with a degree in chemical engineering. Several times a week, he receives tips that are 50 to 100 percent of the tab.

His biggest tip ever was in August: $6,000 on a bill of about $1,500 for three people. (Yes, some pricey wine was involved.) He questioned the amount, he says. “The tip was way too many zeros.”

Sundriyal is quick to say that not every server makes such bank and to credit his co-workers — bussers and cooks alike — for the bounty. “The food has to back it up.” As a server, he sees himself as “the face of the restaurant” and attends to guests based on signals he catches. “There’s no one-size-fits-all” approach to attending to customers. Also, “there has to be emotion” — genuine care — “behind the mechanics” of attending to others.

Andrea Jackson, 54, a server at the upscale Annabelle in Washington who has also worked at the modern Israeli restaurant Sababa, says a trio of diners recently left $150 on a $300 bill. “Are you angels without wings?” she asked them. No, they responded, they just appreciated her. Like Sundriyal, Jackson says it’s not uncommon to receive super-size tips — $100 on a $50 dinner here, $100 on a $100 tab there.

Tom Sietsema's 2021 Fall Dining Guide

Sometimes, customers “give back financially what they’ve been given emotionally,” says the hospitality veteran of more than 30 years. “My M.O. is to give love, to everybody.” Some of her relationships with guests go beyond the dining room. Several guests sent money her way when Sababa closed earlier in the pandemic; others have dropped off Christmas gifts at her home.

Some tippers like to spread the joy over time. Early in the pandemic, the 30-seat Hound + Bottle in Bremerton, Wash., was closed except for Fridays, when owners Jodi and Alan Davis offered takeout dinners. One customer, a retired shipyard worker, routinely ordered online, picked up his food wearing a mask and slipped a crisp $50 bill across the counter.

“This went on for months,” until the restaurant reopened for full service in July, says Jodi Davis, who remembers the customer as a man of few words named Dan, and only because that’s the name he signed on his credit card slip. “It was huge. People like him kept us going.” Dan the Fifty Dollar Man, as he came to be known, put “wind in our sails.”

Ehsan Bassam, a generous tipper willing to go on record, says, “I like servers who treat their work as careers rather than jobs.”

A financial adviser who splits his time between the District and Miami Beach, Bassam maintains the schedule of a restaurant critic, eating out every day. He figures he spends between $80,000 and $90,000 a year on meals away from home. “My fridge is empty and I haven’t gone to a grocery store in two months,” Bassam says. “I’m a millennial that never learned to cook and I like to go to places with good company.”

Two or three times a week, he visits Afghan Bistro in Springfield, Va., or its dressier sibling, Aracosia, in McLean — wherever manager Eve Masroor, one of many family members behind the popular Afghan eateries, happens to be working.

As their homeland fell to the Taliban, these Afghan women rose to lead a D.C. restaurant empire

Masroor, 35, made such an impression on Bassam and his family when they first visited Afghan Bistro, everyone in the party of six shook her hand as they left the restaurant. These days, his order tends to be, “Eve, you pick.” (Bassam sounds easy to make happy. His advice to anyone serving him: “Keep my drink refilled, whether water or iced tea. I like never having to ask.”)

Masroor, who says she gives the same service to everyone and “wants customers to feel as if they’re dining in our home,” says Bassam typically leaves between 55 and 65 percent of the bill, “sometimes 100.” While she’s grateful for the money, Masroor says she gives it to her servers to split. Her advice to her staff: Be formal and charming, but “be yourself” and “get a feel for the guests.” She knows the menu as well as anyone in the kitchen — “all the herbs and garnishes. They’re my mother’s recipes.” She also likes to send out gratis drinks and desserts to customers to “build rapport” and get feedback.

It happened a decade ago, but longtime Washington waiter Jonathan Crayne, 66, remembers two things that helped land him his biggest tip in his 45-year restaurant career: $10,000 from a Canadian real estate developer hosting some business types at the high-end Marcel’s. One tactic was his honest wine recommendation, a Jordan cabernet sauvignon, which was challenged by the somber host, who pointed to a far more expensive cult wine on the list. Why not Screaming Eagle — then priced at $5,000 — the developer wanted to know. “Jordan is what I like,” Crayne told him. (“I’m not a seller,” says the waiter. “I only sell myself.”)

A reopened Marcel’s reminds me that fine dining, especially now, is about more than food

At the end of the meal, the diner told Crayne: “We never laugh. If you can make us laugh, I’m going to give you a tip that hits The Washington Post.”

Crayne told the party about growing up poor and Jewish in Baltimore, and walking five miles to school with his sisters. “But that’s sad,” said the host. Crayne wasn’t finished. “But we did it in fish nets and high heels!” he said, to laughs all around.

Crayne’s boss, chef-owner Robert Wiedmaier, asked the waiter to share the largesse with the team, which he did. The generous Canadian returned to Marcel’s three more times — and left tips totaling $30,000. A couple years ago, Crayne was surprised to find the big spender in the bar. “I went through a brutal divorce,” the VIP told the waiter. “I’m not a billionaire, just a millionaire.”

Per usual, Crayne told him a joke. Despite the man’s reduced circumstances, says the waiter, “he still left $3,000.”

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