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Some people really do want the ring in the food.

Equinox co-owner Ellen Kassoff Gray has witnessed at least a few hundred proposals in her restaurant over the last 16 years. She doesn’t recommend it, but people still ask the staff to present the engagement ring in a dessert or glass of Champagne. The restaurant won’t bake jewelry into a chocolate cake, but they will place it atop a slice.

“We do it so that they see it, because we really don’t want anybody swallowing that,” she says. A server or manager is usually standing close by “to make sure that there’s a timely reaction to the foreign object in their food.”

With Valentine’s Day around the corner, restaurants will no doubt be filled with more “will you marry me?” cliches, even though Christmastime and spring are more often regarded as proposal season in the restaurant industry. What’s a once-in-a-lifetime moment for most is a relatively routine part of some establishments’ operations. Still, dealing with a proposal from the restaurant’s end can sometimes require much more than Champagne.

1789 Restaurant in Georgetown sees engagements as often as once or twice a month. General Manager Richard Kaufman admits it’s a little nerve-racking: “Everyone knows, they’re watching this guy; He looks nervous, but the girl doesn’t know. We’re making sure nobody spills the beans.” Kaufman says they once came close to a spoiling a proposal when a server blurted out “congratulations” before the guy actually popped the question.

In almost all cases, restaurants are tipped off in advance that a proposal is coming. But Trummer’s on Main co-owner Victoria Trummer says it’s useful to know at which point in the meal it’s going to happen. She recalls one guy who requested that two glasses of Champagne to be served once he proposed. But during the couple’s dinner, the staff couldn’t tell if he’d made the move or not. “There was never any glee or big kiss or anything, so we didn’t know when it happened. We literally had no idea. Maybe she said ‘no,’ then we don’t want to bring the Champagne out,” Trummer says. Finally, Trummer went to the table to pour water and looked down to see the ring on her finger. “Usually when there’s a proposal, everybody knows. Sometimes the whole restaurant claps because she squeals or he gets on his knee.” 

Trummer says the earlier someone can give them warning, the better, especially if they have specific requests or want a prime table.

In fact, some fine dining restaurants have proposal tables—specific seats that are almost always dedicated for soon-to-be-engaged couples. At Marcel’s, which sees two to three proposals a month, maître d’ Adnane Kebaier usually has a private corner table in mind. But there are exceptions: “If I feel at the door that probably she’s going to say ‘yes,’ and they look happy and everything, I put them where people can see that. Because most of the people they want to enjoy the applause for them,” he says. Sometimes, Kebaier will even take a video of the proposal on his phone to later send to the couple.

Other couples apparently like to bring their own crew to document the big moment. At 1789, Kaufman recalls once hiding a couple’s friends so that they could film the proposal. “We had to coordinate timing with them so pretty much the moment he did it, they could come into the dining room with a video camera,” Kaufman says. “It wasn’t as smooth as you might hope.”

Things went far smoother at Trummer’s On Main, where one guy arranged for a photographer and three-piece band at his proposal last year. Victoria Trummer says the proposal took place on the balcony of the Clifton, Va. restaurant; the photographer was hidden away until they were in position, and as soon as she said “yes,” the band came out to perform. “I’ll never forget this guy. He was so nervous, so excited. He wore this really cute suit with a bowtie,” she says.

Overall though, most restaurant proposals aren’t too crazy or elaborate. (They decided to propose in a restaurant, after all.) Restaurant Eve and PX co-owner Todd Thrasher says the most elaborate one he’s seen was from a guy who rented out the entire front room of PX and decorated it with dozens of white roses and candles. Another time, at Restaurant Eve, a man put the ring in a box buried under what looked like $1,000 worth of scratch-off lotto tickets.

More often than you might expect, the person proposing entrusts the ring into the hands of the restaurant staff for the grand reveal. Kebaier says people will sometimes bring their ring to the restaurant as early as a day or two in advance, and he’ll hold it in the office safe. When it’s time, Kebaier likes to put the ring on a nice plate, cover it with a cloche, and present it between dinner and dessert, as if it’s an extra course from the chef (complete with fork and knife to build the illusion).

“Every time they give us the ring, I feel like it’s a sitcom setup,” says 2941 Pastry Chef Caitlin Dysart, who’s often tasked with placing the ring on a dessert. She tries to make the diamond as visible as possible so there’s no mistaking that it’s there. To avoid getting the ring dirty and sticky, she typically places it on a raspberry or some kind of decorative chocolate. “I’m not going to put it on any ice cream or mousse,” Dysart says.

Chocolate desserts are usually the sweets of choice for the sparkling garnish, although Dysart recently made a croquembouche (a pyramid of pastry balls) for a proposal at the Falls Church eatery. One of her more highly coordinated tasks involved a bait-and-switch proposal that was meant to trick the would-be bride into thinking she was at the restaurant for a birthday party. Dysart made one birthday cake for the couple’s friend, and as he blew out the candles, the staff brought out a second cake that said “Will you marry me?”   

Rejections are fairly rare. Thrasher recalls just one proposal gone bad in Restaurant Eve’s nearly 12 years: “There was a discussion, tears were shed by both people, and they asked for the check. And the ring never made it to the finger.” Similarly, Kebaier remembers only one failed proposal in his 17 years at Marcel’s. The couple actually laughed it off—and they’ve since gotten married and still return to the restaurant together.

Other times, a diner might write in an OpenTable note that they are planning to propose, but then nothing happens. Dysart remembers waiting for a guy to pop the question one time at 2941—and then he ordered a cheese plate. “I was like, ‘Nope, not happening,’” Dysart says. “That’s a bad sign. That’s not romantic.” 

Kassoff Gray finds there’s a certain type of person who proposes in a fine dining restaurant. They’re often hopeless romantics and sometimes “a little bit on the cheesy side—we can’t get away from that.”

But as much as Kassoff Gray sometimes wants to roll her eyes at some of the cliches, she and her staff can’t help get sucked into the love too. “It makes everybody have a great night at work, and what’s wrong with that?” she says.

Plus, those people often come back year after year for anniversaries—and other occasions.

“The babies coming back are the best,” Kassoff Gray says.

Illustration by Lauren Heneghan