Most Memorable Valentine's Day Stories

From ill-fated proposals to presidential visits, these are the best Valentine's Day tales from industry insiders

Ah, Valentine's Day: The only time of year when it's not only acceptable but expected to start off the night with Champagne and end it in tears. Sure, with the right chocolate dessert and drinks like our favorite bourbon-hibiscus cocktail with Champagne ice (see the recipe), it's not all bad. But while many couples can easily boeuf for two without breaking up, the high-stakes holiday all too often brings out the scarier side of romance—from botched proposals to ill-timed breakups.

No one knows the potential for disaster better than the bartenders and waiters serving the Romeos and Juliets across the nation. Which is why we've asked our insiders for their most memorable Valentine's Day stories, plus a little advice to keep you and your date off the list below. Take it from the men and women who will actually be cleaning up the mess—literally and figuratively—at the end of the night. They know what they're talking about.

① Anything Can Happen

"Back in 2012, I was head bartender at Minibar, José Andrés's sought-after, avant-garde dining experience in Washington, D.C. That Valentine's Day, we were just about to open the doors for our first seating when Secret Service agents and lights from the presidential motorcade started to flood the restaurant. For security reasons, the White House does not give out advanced notice, so we were, of course, surprised and unprepared with the arrival of Barack and Michelle Obama. I will always remember the rare honor I had of preparing President Obama's Belvedere martinis with liquid olive." —David Strauss, Sheppard and The Morris, Washington, D.C.

② The Accidental Proposal

"One Valentine's Day, we gave the ring to the wrong girl. The guy who had to tell his girlfriend he wasn't actually proposing was furious." —Zach McGrath, Kitchen Manager at Waller Creek Pub House, Austin

③ Going to the Chapel

"A server I worked with met a guy at the bar drinking alone on Valentine's Day 2012. They went out when she got done, went to the courthouse three days later and got married. It lasted four months. They had a great party though." —Ashley Schultz, Bartender at Chauhan Ale & Masala House, Nashville

④ Bad Romance

"There was a guy taking his valentine out for dinner, and he specifically asked for the community table. We sat them there, in between about 10 other diners. During the meal, and much to the horror of myself, the servers and other guests around him, he begins to break up with his date. I guess he was hoping she wouldn't throw a fit around all those other people. He was really, really wrong." —Beth Black, Co-Owner of FoodE, Fredericksburg, Virginia

⑤ A Crying Shame

"A guest came in and asked myself and the venue manager to help with an elaborate plan to propose to his girlfriend. He had us put the ring in the dessert, and we were prepared to come out with sparklers and flowers. When the time came for him to pop the question, she started crying, so we all headed out to congratulate them, not realizing she had declined the proposal. Everyone in the restaurant took notice, and needless to say, the evening came to a dramatic pause." —Anonymous, Server at STK South Beach, Miami

⑥ All You Need Is . . . Morrissey

"This one particularly slow Valentine's Day, a single man and single woman were sitting at the bar. I put Morrissey on, kind of ironically, and it was like the misery gods brought them together. I've never seen two people so elated over sad music! My tip was double the bill, and I left feeling like a rich Morrissey fanboy Cupid of sorts." —Patrick McAndrew, Host of Heritage Radio Network's Why Food? and Bartender at The Spotted Pig, NYC

⑦ Absinthe Minded

"Never order absinthe on the first date, especially on Valentine's Day. I had this customer decide to drink it like a college frat boy and was just a stammering idiot by his second drink. Needless to say, his date wound up going home with one of my regulars instead. I may have played wingman for my buddy." —Warren Bayani, Bartender at Chao Chao, NYC

⑧ The Show Must Go On

"At my previous job, we once had a gentleman call ahead to reserve the best table in the house for a date. As time went by, the gentleman's date was nowhere to be found. I could tell from the look on the poor guy's face that he had been stood up, but that didn't keep him down. Two bottles of our best wine and a four-course meal later, this man ended up having one of the best meals of the night." —Anonymous, Bartender at Sophia's, Austin

Now that you've enjoyed a few of the more memorable tales these fine industry folk have witnessed firsthand, here are some pointers on doing Valentine's Day right.

Let them help: "This holiday is everything! I'd encourage the lovers out there to reach out to their favorite bartenders, managers, servers, etc. We can have a favorite song played, or send out special chocolates or Champagne. That frees you to focus on happy experiences." —Maggie Dandrea, Bartender at Bayou Bar, New Orleans

But stay in your comfort zone: "Valentine's Day should be a relaxing chance for you to focus on the person you love, not worry about the bill or the food or the wine. At my old restaurant, guys would come in and spend half the time trying to nickel-and-dime the server over portion sizes and menu prices. There's nothing romantic about that." —Chris Poldoian, General Manager at Camerata at Paulie's, Houston

And leave a proposal out of it: "There are too many variables at stake! I've seen engagement rings in Champagne flutes go to the wrong table: Now that's a day they'll never forget!" —Katherine Paulino, Server at Holler & Dash, Nashville

Mind your manners—and your hands—no matter the occasion: "Normally, I'd consider myself to be a reasonably romantic guy who's not afraid of the occasional PDA, but there's something about Valentine's Day that has convinced the dining public that February 14 is the day to throw caution to the wind and embrace their exhibitionist sides! I've had to break up more than one couple who were getting a little too hot and heavy for the comfort of surrounding patrons." —Philip Dizard, Morimoto, New York City