It was Valentine’s Day at Cashion’s Eat Place about a decade ago, and a guy was preparing to propose to his girlfriend. The evening started smoothly, and the couple was waiting on dessert. Co-owner Justin Abad, a manager at the time, was standing by with his nicest bottle of Champagne.

At last, the guy got down on one knee. By chance, Abad recalls the music was in between playlists, and the place got quiet. The entire restaurant looked at the couple’s table—in the middle of the dining room—and let out a collective “awww.”

“He’s got this huge smile on his face, and he’s got this beautiful ring presented,” Abad says. “She looks at him and turns completely white, does not say a single word, gets up from the table, and walks out the door.”

The guy remained frozen with a knee on the ground holding the ring out. The collective awww turned into a collective gasp. Abad left his tray with Champagne and two glasses on a table and picked the man off the ground by the arm. “I said, ‘Sir, why don’t you come to the bar with me,’” Abad recalls. “He had clutched in his right hand this ring—just clutched open in the box, just staring at it. And he was completely taken by surprise.”

Abad told the bartender that whatever the guy wanted to drink was on the house, as was his dinner. The man proceeded to get completely hammered. Then he tried to pawn the ring off as a tip. “He was like, ‘Well, I’m not going to need this, I’m sure of that.’ We were saying, ‘No, no, no, maybe…’ He goes, ‘No, she just texted me. It’s over. It’s done.’”

The man threw the ring on the floor. “We’re like, ‘Oh no, that’s not happening,’ so we grab the ring, put it inside his jacket pocket,” Abad says. They hailed the guy a cab and handed the driver $50, warning him not accept the engagement ring as payment.

“It was the most painful thing I’ve ever witnessed probably in my entire life,” Abad says.

He never saw the poor soul again.

Restaurants are privy to all sorts of relationship milestones: engagements, first dates, anniversaries. Breakups are no exception. While they’re not usually as frequent as other occasions, industry veterans have all seen someone left crying at a table or with a drink in the face. Being prepared for the implosion of human emotion is all part of the job.

“I actually do think it’s worse than being broken up by text message,” says Black Squirrel owner Amy Bowman of restaurant breakups. While alcohol might seem like a good idea to soften the blow, it often only fuels regrettable outbursts. And while a public setting may temper a bad reaction, that’s not a guarantee. If there’s a scene, the walk of shame is unavoidable. “You’ve got to get out of there somehow, and everyone’s looking at you,” she says.

Bowman knows because she was dumped at a fancy French restaurant when she was 19 at Pepperdine University in California. It happened right in the middle of their entrees. “You couldn’t escape. It’s like a trap,” she says. Making matters worse, they’d shared a ride to dinner. “I just sat there trying not to cry and looking at my food, going ‘I can’t believe this is happening to me.’”

Most restaurant staff takes a hands-off approach to breakups, but sometimes there is the temptation to get more involved. Just after Slipstream opened last fall, a woman entered the 14th Street NW coffee shop and cocktail spot looking for a table for two. Owner Ryan Fleming offered her a prime spot by the window. “No, no, no, I’ll have that seat in the back corner,” she said, explaining that she was about to break up with someone.

Fleming, a first-time restaurateur, and the host huddled: What was the code here? Should they give the guy a head’s up? “It almost feels wrong letting him just walk into it,” Fleming says. Of course, in the end, they let it go. It wasn’t their place to meddle. “The whole time they were there, everyone was afraid to go over to give them water,” Fleming says. The couple sat there for two hours with just one round of drinks. They left separately.

Fleming has been there, too. The Slipstream owner once broke up with a woman at a barbecue place in New York. Why barbecue? “I don’t think people make a lot of good decisions when they’re doing that. My mind was consumed with the one decision I was making that day.” Adding an even more bizarre element to the situation: they were sitting next to one of the stars from The Office, although Fleming can’t remember which one since he doesn’t watch a lot of TV. “While we’re in the middle of tears, we’re also starstruck and wondering what this guy is thinking of us.”

Is there a “right” place to break up with someone? In City Paper’s recent Food Issue, I suggested Afterwords Cafe, attached to Kramerbooks. Aside from the aptness of its name, the low-key bar has plenty of cakes to consume as you eat your feelings and books just next door for emotional support. “Also you could lose yourself in a really good novel,” says Events Director Sarah Baline. She says breakups do happen there, although not all that often. “We hope people come in not to break up, but if they do, we’ll be here with a shoulder,” she says.

Capitol Lounge co-owner Jimmy Silk suggests the best place to break up with someone is at one of the eateries at Union Station. He has a few friends who’ve specifically used the transportation hub for that purpose. “There are so many options for escape: trains, Metro, taxis, bikes, car share,” he explains.

Meanwhile, Abad of Cashion’s Eat Place highly recommends not breaking up at a restaurant. But if you must, do it at the bar, not a table. “It’s transient. There’s more energy there. You’re not locked in and committed to an experience. And frankly, do you want to sit there after you break up and continue dinner?” he says.

That advice, apparently, is not well heeded. In his experience at Capitol Lounge, Silk says planned breakups happen exclusively at tables. “I don’t know if this is due to the fact that the person doing the breaking up would rather sit across from the person with sharp objects next to them… or they just want more privacy,” he says.

In the five or six times Silk has witnessed a breakup at a table, no one has eaten anything. They sit down, order drinks, and get down to business.

And then there are the unplanned breakups.

Capitol Lounge bartender and manager Lucas Lally remembers a quiet Sunday night about three years ago when there was just one guy sitting by himself at the bar. There was no music, so the bartender, Lally’s roommate, walked over to the jukebox. As he was selecting a song, a girl came flying in, sat next to the guy at the bar, and started laying into him. “Fuck you. You’re an asshole. It’s over,” Lally recalls of the conversation.

Then the bartender’s song started to play—“Istanbul was Constantinople. Now it’s Istanbul not Constantinople”—and the woman picked up the guy’s beer, threw it in his face, and walked out. “The bartender and I just started laughing because the song was timed so perfectly that it happened immediately as everything escalated,” Lally says.

Lally isn’t sure what the guy did to deserve a beer in the face—but they still charged him for it.

Commissary General Manager Heidi Minora hasn’t witnessed such “serious Jersey housewife explosions,” but she has seen a lot of breakups at the Logan Circle restaurant. On average, she estimates there’s usually at least one per week, but she’s seen as many as two to three in a single day.

Most people on the verge of a breakup request a booth tucked away in a corner. “It’s a very intimate table, which works on a lot of different levels, but that’s the breakup spot,” she says. “If it’s going to go down, it’s definitely going down at that table.”

Nine times out of 10, Minora says the breakup happens after entrees but before dessert. From the restaurant’s perspective, the worst scenario is when the couple gets into the bad news before they’ve even ordered. “You can only go over so many times and ask somebody what they want to order before they’re like, ‘Listen, I haven’t even looked at the menu. My life’s about to change!’”

Most breakups aren’t quick. If there’s one in progress, the staff at Commissary guesses the table probably isn’t going to turn on schedule and rearranges reservations accordingly. For servers, a breakup can mean everything from a big tip (if the guest wants to apologize for an emotional outburst) to nothing at all (sometimes they just want to split fast).

Minora says the worst thing a server can do is ask if everything is OK. “That’s basically like watching The Notebook and crying and somebody being like, ‘Are you alright?’ Of course I’m fine, leave me alone, I’m crying, it’s a sad movie,” Minora says. “You’ve kind of just got to let them do their thing.”

But if the heartbroken heads to the bar and wants to spill his or her heart out, there’s usually a bartender there to commiserate and sometimes comp a drink.

“You can come and drink a glass of water at our bar, and our bartenders will listen to all your problems. I think they’re just like the therapists of the city in a lot of ways,” Minora says.

And, she adds, who knows? “Maybe you’ll meet somebody at the bar.”

Illustration by Robert Ullman