Food & Drink

NYC Restaurant Servers Share Their Craziest Valentine's Day Stories

Daniel Fishel/Thrillist

New Yorkers know that trying to secure a reservation for Valentine's Day is no easy task -- it's one of the busiest nights of the year for restaurants, with tables often fully booked weeks in advance. That means that servers and bartenders are pretty much guaranteed to turn a higher profit than almost any other night -- but it also means they get a close look at all of the holiday’s inevitable mishaps and train wrecks. As a server at several restaurants in the city, I've seen many of these incidents firsthand, but I've also collected these stories from fellow servers who have worked everywhere from Per Se to The Spotted Pig. As it turns out, when you look past the chocolate roses, squeeze-to-sing teddy bears, and bottles of Veuve Clicquot, you witness a pileup of barf, betrayals, and straight-up buffoonery.

Next time, keep your napkin on your lap

"A couple of years ago, I was serving a couple and I noticed that the guy was holding eye contact with me longer than most customers do. His girlfriend didn't seem to notice. Toward the end of the meal, she got up to go to the bathroom and while I cleared their table, he slipped me his name and number on a paper napkin. When I looked up at him he held his finger up to his mouth as if to say 'our little secret' and winked at me. Flattered, I slipped his number into my apron. Minutes later, I came back to drop his credit card receipt on the table, and as I was pulling a pen from my apron, the napkin came out with it! His girlfriend did a double take and her jaw dropped open. His face turned bright red, totally speechless. I quickly told them to have a wonderful night and ran to help other customers." -- Chris, 37

An accidental engagement

"Last Valentine's Day, I had been recently engaged and I wasn't yet used to working in my ring. Before I brought dessert to a couple in the corner of my section, I quickly dropped some dirty plates in the dish pit. I hadn't realized that my hands had gotten sudsy and my ring was loose on my finger. As I was presenting dessert to the couple and gesturing to the various ingredients ('We have chocolate cake with an almond crust and a dollop of whipped cream on top') my ring slipped off and landed in the whipped cream. It happened so fast and subtly that when the woman saw the ring, so many emotions crossed her face. She looked confused and excited and hesitant and he looked shocked, but neither of them could speak. Laughing to ease the tension, I quickly picked up the plate and said, 'I'll have the kitchen make you a fresh one!' When I dropped off the ring-less desert, they immediately asked for the check. I haven't worn my ring to work since." -- Marie, 29

Rule #1: Keep your eyes open

"It must be nerves, but I never see guests as [inebriated] as they are on Valentine's Day. Last year, a man arrived about an hour before his date, and he planted himself at the bar until she joined him for dinner. He had completely slipped my mind until a couple hours later when I saw my manager standing firmly over his table. The man was holding his pen suspended over the check, essentially asleep with his eyes open. It seemed like 10 minutes my manager was waiting. Finally the man signed what appeared to be a single line and then proceeded to pick up and drink from the water glass on the table next to his. At that point, my manager called over the sommelier, and together they scooped the guy up and carried him out by his arms. Moments later, his date excused herself from the table and hailed a cab outside the restaurant alone." -- Rachel, 21

Not your usual Pretty Woman

"Sometimes when a couple is notably mismatched -- for example, he's middle-aged with hair plugs and she's part silicone -- it's a sign that he's paying for his dinner and his date. This happened often when I was working at a very highly regarded Columbus Circle fine-dining restaurant. It was pretty obvious these people weren't a real couple but they still seemed to be enjoying their time, she especially. In fact, she was having too much of a good time because between the first and second course that good time came right out of her in the form of projectile vomit. Her date threw his arms back, shocked, and she was totally unfazed, practically falling asleep at the table. We escorted her (see what I did there?) out of the building, and instead of leaving, her date simply moved tables and savored the remainder of his five-course meal." -- Jason, 30

We're going to need a mop

"This was early in my career and I was working in a fine-dining restaurant with carpeted floors on the Upper East Side. We had a very old woman -- so old this may have been her last Valentine's Day -- pull her pants down in the middle of the floor and urinate on the carpet. She was just completely unaware, which I think saved her a lot of embarrassment. In good form, the waitstaff and the guests surrounding her treated the situation gently and we were able to clean it up pretty quickly. We comped her meal as well (and held back on refilling her water glass too readily)." -- Al, 40

Customer satisfaction

"Cleaning up after tables can be the worst part of serving, but it was never worse than the first Valentine's Day I was a server. When this couple wasn't drinking and eating, they were making out. I'm not sure how they didn't faint of low oxygen intake during this meal. I knew they were nasty but I didn't realize just how nasty until I picked up their cloth napkins once they had left, and one of them was slimy. I threw the napkins in the laundry bag in the kitchen and when I looked at my hand there was no denying that it was covered in… his happiness. I screamed at the top of my lungs and ran to the dish pit to sanitize my hands in industry-grade dish soap. The only thing that keeps me from having nightmares is that they gave me a 30% tip."-- Annalea, 26

A family affair

"One V-Day I was serving a man and a younger woman who looked like a couple out of a movie. He was studious and handsome with silver hair and she was dressed eccentrically in a fur coat with purple highlights in her hair. We developed a lovely rapport with each other -- they were warm and polite to me and I appreciated the gentle nature of their romantic gestures. Rather than the gross PDA some customers partake in, they were subtly holding hands across the table while rapt in conversation. I started to wonder about their relationship. Maybe they were both widowed, she as a young bride and he later on in his marriage? Maybe they were student and teacher who couldn't deny their attraction once the semester ended? When I dropped the check, I decided to be open and ask, 'How do you two know each other? You're the loveliest couple.' They looked at each other and looked up at me with disgust. He said, 'She's my daughter.' All I could say was, 'Oh!' He left me a very small tip. That was the night I learned, either keep your mouth shut, or wait until they've already tipped you to ask the burning questions." -- Whitney, 24


"This was one of the busiest Valentine's Days I've ever worked. After the big push to get everyone seated, fed, and satisfied, the staff started to get into that slaphappy mode where we know the night is nearing the end. I was working as a line cook and I noticed one of our sous' had been missing for quite some time. He was a bigger guy and I was worried he had had a heart attack in the bathroom or something. Our executive chef followed me to the back and after knocking on the staff bathroom door a couple times, we finally decided to kick it open. There he was, alive and well, having sex with our host! I guess everyone was feeling the love that night. While they were still sitting intertwined on the toilet, the executive chef barked, 'Pack your bags!'' and headed back upstairs like he had never seen a thing. That was the only time I've seen a chef fired on the spot." -- Benny, 28

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Hillary Waldstein is a writer and a restaurant server living in New York City. She's never seen a server sneeze in someone's food, for the record. Follow her on Twitter @HillWald.