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The 5 Worst Moments of My Serving Career

I referenced this  topic with a friend a couple of weeks ago, so I thought it might be worth putting together my most embarrassing serving moments in an archive for all time.

I’m sure other people have far more extensive lists than I do. My waitressing stint was relatively short, spent across two restaurants for a grand total of about seven months. But in that small window of time, I managed to embarrass myself a lot.

I might possibly be the worst server ever, which is why I opted to take my customer service skills elsewhere.

1. The time I brought a man his martini too soon

During one of my first solo shifts in a college bar in Boston, I had a  group of family friends or something like that. They gave me their drink orders: a couple of wines, a couple of beers, a couple of cocktails. I went to ring them into the computer, taking time to type in one guy’s martini order, for which he gave very specific instructions, and insisted I write down so I didn’t mess it up.

The restaurant was dead, so Ron, the manager/bartender on duty grabbed the ticket and started making them quickly and aggressively.  He was one of those guys who prematurely went gray in his 30s, but was tall and buff and super bro-y. Most of the girls had crushes on him, but he scared the shit out of me. He never said much, but was quick to judge, and liked calling people out for being stupid or lazy.

I brought my tray over as he was lining drinks up at the server’s station.  He turned his back and walked to the other side of the bar, so I loaded up the drinks and brought them to the table. I carefully placed them in front of each person, leaving the martini for last.

“Your dry martini with [insert brand here] vodka and no olives!” I said proudly after setting the glass down spill-free.

He looked at it for a moment, then looked at me.

“What is that?” he asked.

“A martini,” I answered. “Dry. With no olives. Isn’t that what you asked for?” I smiled at him, doing my best Vanna White to demonstrate that – ta da! – here it was.

“Yes,” he chortled. “But this isn’t a martini!”

I looked down at the glass, with its clear liquid and ice cubes swimming around in it, then back toward the bar. Ron was standing there with a drink shaker still in his hand. At first, he looked completely dumbfounded, his face flaccid and a snarl on his lips. Then he burst out in laughter.

I snatched the glass from the table and brought it to the bar, where Ron emptied the ice water mix he was using to chill the glass, and refilled it with the actual drink.

“Now, it’s ready,” he said, shaking his head in disappointment.

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2. The time I spilled beer in a frat guy’s hood

One rainy Friday afternoon, a group of about 15 frat guys came in and sat down in my section. This should have been a gift from god, because it meant I stood a chance at making some money during my shift … but it quickly dissolved into a disaster.

“I’ll have a Miller Lite,” “I’ll have a Bud Light,” “I’ll have a Bud Light,” “I’ll have a Miller Lite,” “Miller Lite,” “PBR,” “Bud Light,” “High Life,” “Coors Light,” “Miller Light,” “Coors Light,” “Bud Light,” “PBR,” “PBR,” “High Life.”

Great, so 15 domestics to different people all dressed similarly? I can keep that straight.

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At the peak of their rapid-fire ordering, I was just running back and forth between the table and the server’s station with trays full of full beers, and then empties. The bins were overflowing with glass bottles, and the bartender rolled his eyes at me every time the little printer went off behind the bar to signal I’d sent another order through.

“PBR,” one guy said me as I returned to pick up bottles.

“Of course,” I smiled apologetically, realizing that I’d forgotten it on the last few rounds. I rushed to put it in the computer and pick it up from the bar, so I could bring it to him right away.

But when I was speed-walking to the table, I tripped and caught myself. We were required to carry drinks on trays, even if we only had a single drink. This tray had just one PBR can on it, and the can toppled over. It spilled out all over the tray.

Phew, I thought. Mess contained. 

But when I grabbed the beer to upright it, the tray tipped and dumped the liquid straight into the guy’s rain jacket, which was hanging over the back of the seat. It was a deep puddle of beer in a hood specifically designed to be impermeable.

How do you begin to clean that?

The whole table stopped drinking to watch as I got down on my knees to unceremoniously pour the beer out of the hood onto the floor and mop it up with paper towels. At least he wasn’t a jerk about it.

3. The time I found a poop on the floor

One of the job duties in an afternoon shift was to clean the bathroom once a day. You had to go in, spray down the counters, restock the toilet paper or soap, give it a sweep, make sure the trash can wasn’t overflowing with paper towels. The basics.

Everyone hated cleaning the bathroom. They felt like it was demeaning and resented having to do it. I didn’t mind.  It meant a few minutes of privacy when I didn’t have to make small talk with customers (I’m such a people person). So I usually volunteered for bathroom duty.

But one day when I was sweeping, I stopped dead in my tracks. There was a poop on the floor next the toilet.

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What? Why? Who does that? How did it even happen?! A single poop!!

The only thing I knew for sure was that I didn’t get paid enough to pick it up.

4. The time a couple broke up at my table

I had a couple come in and sit down at one of my tables. I could tell things were bad when I went to take their drink orders. She was sitting with her arms folded tightly across her chest. His hands were draped across the table and his head was down. It had gotten even worse by the time I returned with their drinks. They were audibly arguing and barely stopped when I approached the table. The girl looked like she was on the verge of tears.

“Need a minute to decide?” I asked, ready to get the hell out of there and let them get it over with. But they insisted on ordering a full meal.

Before I could go even return to check on their drinks – they were probably going to need several – the girl was gone. The guy was still there, typing furiously on his phone. I quickly snuck off to the check on the kitchen to see if I intercept their order. Surely, they weren’t going to want to eat after this. No luck. It was already on the grill. When I went back out to the dining room, the guy was gone, too. He’d run out after her.

A little while later, the cook tapped the bell to announce the food was ready. I was ready to go crying to the manager to see if the bill could be wiped. But I saw the guy had returned and was sitting at the table … alone. I carried the two plates over the table and set his down in front of him.

“Do you want this wrapped up to go?” I asked about the other.

He shrugged, “Ok.”

I guiltily slid him the check for both of their bills.

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OK. Thanks. Bye.

5. The time someone did the “bitch cough”

You know the “loser cough”? When someone says something under their breath and pretends to cover it up by coughing? Well that happened to me, but this person was calling me a bitch under his breath.

He was a regular at the place where I worked. He came in nearly every day and ordered the same food and drinks. He was an odd guy, quiet and shy. He was foreign, so I think the cultural and language barriers led to some miscommunications. Namely, all the girls at the place thought he was rude and sexist. I tried to befriend him, but it all went south when he asked me to see him outside of work and I said no.

Walking past his table one day, he looked up at me angrily, and then hunched over and did the “bitch cough.”

I was furious.

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Excuse me? I said involuntarily, and then realized there was no good way out of this. I stared at him for a moment in disbelief and then walked away, glad to know my career in serving was going to be a short one.

What are your best stories from the trenches? I’d love to hear them!


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