A Rough Start

I had been a waiter for almost a year.  While studying film in college, I figured it was important to invest in my future, so I got a job at a restaurant on the South Boston waterfront.  With no service experience under my belt, I was hired as a food runner.  After working for a few months and becoming familiar with the menu, I was promoted a server position.


My big break.

Welcome to the major leagues Marty.

On my first day of training, I shadowed my co-worker who I will call Hugo (because that was his real name).  Hugo was one of the best servers at the restaurant– hardworking, fast, and great with customers.  With his thick Colombian accent and affinity for performing all tasks at the fastest possible speed, Hugo’s training methods did not mix well with my first day jitters. Luckily, the night got off to a slow start, and Hugo had time to walk me through most aspects of serving before any customers came in.

When two women in their early thirties walked through the door I greeted them with a smile and showed them to their seats.  They were old friends who hadn’t seen each other in a while and were clearly excited for a night of catching up.  Two friendly people in great moods, the perfect first table.

“Don’t worry Hugo, I got this.”

I approached the table and took my first ever drink orders: Cabernet Sauvignon and red sangria.  Relieved to hear drinks that I was familiar with (if they had asked me to describe a “Basil and Thyme Gimlet” I may have just walked away), I made my way to the bar to place the order.  While the bartender made my drinks, Hugo showed me how to properly carry a drink tray.  I practiced placing my hand beneath the tray, feeling the weight of it shift as I lifted the water glasses off.  I was a little shaky, and certainly not entirely comfortable, but I got the idea.

When the drinks were ready, I placed them on a tray and slowly made my way to the table where the two women were sitting.  The top-heavy wine glasses proved more difficult to balance than the stout water glasses I had practiced with, but I made it to the table without incident.

“Ooooh look at that!”

The ladies were impressed with the large sangria glass filled with fruit.  I placed the sangria on the table, but when I went to grab the Cabernet, it wasn’t there.  I stared at the tray wondering where the wine glass could have possibly gone-

“Oh my God!”

It was too late.  The glass lay on its side on the table, its lip pointing directly at the woman who had ordered it.  My first thought was how lucky it was that she was wearing black, but as she stood up, I saw the massive red stain on the front of her white skirt.

I didn’t know what to do.  I picked up the glass, apologizing profusely as I tried unsuccessfully to mop up the wine that covered the table.  My manager rushed over, also apologizing, showing her to the bathroom, saying the restaurant would cover her cleaning bill, but it was futile.  The women were very nice about it, but it’s difficult to expect people to enjoy a night out at a restaurant while one of them is soaked in wine, so they left.

Out the door walked my first table, to whom I did not serve any food and whose night I effectively ruined.  The worst possible start to my career as a waiter.

It was a few hours before I gathered up the courage to serve another table and weeks before I touched a tray.  To this day, I get nervous when carrying multiple wine glasses.  But now, whenever I begin to serve a table I think “I’ve already spilled red wine on a woman’s white skirt, how much worse can I do?”  And so far, nothing has come as close to answering that question.

Having set the bar so incredibly low on my first day, my performance as a waiter since has been (by comparison) nothing short of brilliant.