I Am A Horrible Waitress

So I was just doing an interview in which I was asked about my decidedly odd employment history, which has included stints as a waitress at Upstairs at the Pudding (a schmancy restaurant in Harvard Square that is apparently now called Upstairs on the Square) and a bartender at Hogs ‘n’ Heifers (the place in the Meatpacking District where the bartenders clog on the bar and blow fire, a la Coyote Ugly), and I got to remembering just how really terrible I was at waitressing (not bartending; I wasn’t half bad at that, but I’ve also worked mostly in comparatively hard-to-screw-up beer-and-shots-type places).

The job at the Pudding was the first waitressing gig I’d ever had, and I totally lied to get it, saying that I’d worked at several places in NYC previously (hint: that tends to be the only way to get your first job as a server or bartender if you live in a major metropolitan area. Do NOT take those bartending classes; you’ll figure it out as you go, promise). I wasn’t bad at remembering specials, or at chatting with customers to up my tips, but when it came to balancing drinks on that damn tray…well, the very idea filled me with horror. You know how you see those cocktail waitresses just sailing through crowded lounges, dozens of martinis perched delicately on the tips of their fingers? Can’t do that.

Anyway, one of my first busy shifts was on Easter Sunday, when it seemed that just about all of Cambridge’s upper crust came out for the prix fixe brunch and mimosas. Around noon, a very elegant trio – two older women and a younger man – came in and sat down in my station, and all ordered champagne. I slowly made my way through the obstacle course of tables and waiters carrying a tray of champagne-filled glasses, feeling really quite capable and fabulous.

“For you, ma’am,” I said, placing the champagne before the first woman with a flourish.

“And for you, ma’am.” I set down the second glass.

“And…for…oh my god.” The “oh my god,” because as I spun to deliver the third glass of champagne to the young man, my tray tipped to one side, sending the (very expensive) contents soaring over his blue button-down. He was sweet about the whole thing, but I insisted that he hand over his button-down so that I could dry it for him while he dined in his shirtsleeves. J. Press shirt in hand, I went running back to my coworkers, obviously bright purple and just about dying.

“OhmygodthatwasmortifyingwhatdoIdo?!” The oldest and most experienced of my coworkers took me aside.

“I’m going to fix this for you. Just go grab three more glasses of champagne and deliver them to the table. Say ‘Since that one was on you, this one’s on me.'”

I grinned. Cute.

Tray with three gratis glasses in hand, I rushed back to their table, ready to make things right and possibly not get fired.

“Since that one was on you” – big smile – “this one’s on me. For you, ma’am…for you, ma’am…and…”


Again. Yes, again. Now coated in his second glass of champagne of the hour, the man looked up at me in horror…and what did I do?

Drop to the ground, crawl under their table, and hide, of course. Isn’t that what everyone does in such a situation?

I stayed there a moment, pondering how, exactly, to explain both the second spill and the fact that I had my guests’ tablecloth tucked around my ears, and then stood to face the music. Again, the man was sweet about it (maybe a tad less sweet this time), but my boss…well, let’s just say I wasn’t fired, but I definitely lost the day’s tips to cover their meal and then some.

The moral: I am a horrible waitress. That’s not a moral, you say? Was to me.

Posted by Jordan Reid, 7/7/10.

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