A high-tipping regular was obsessed with getting bossed around. The customer is always right, right?
Jenny Chang / BuzzFeed
"Swab the deck, err…matey." I said, disguising my stuttering with the growl we've come to accept as a pirate's favorite exclamation. "Arrr... swabbie, and then use the, um-arr, tip o' yer dirty mop t' shine me shoes!"
Did I sound more Irish than pirate, I wondered?
I looked around to see if any of the nearby customers were listening. Just Steve, who seemed quite pleased with my mediocre impersonation.
"Avast ye!" I added, worried I might be overdoing it now.
"I'll be right back, matey," I said to Steve. I rushed away to clear some plates, ask Max the bartender to make another round of drinks for the first date sitting by the bar, and enter into the computer system food for the older couple by the window.
Flatbreads, extra pesto, no pine nuts, I typed in just before the iPad screen froze.
Steve had been coming into the stylish Italian restaurant where I worked on the Upper West Side for about a month and a half. At first he seemed like the kind of guy you encounter often as a waitress: the older man, sitting alone, often divorced, who clearly wants to chat. Lonely, a bit flirtatious, but nothing shocking. Steve told me the night we met that he was in his sixties, divorced three times, no kids. He casually made it known that he had money, at first working it into conversation the way people do when they want to seem like they couldn't care less.
"I'll be going to the house in East Hampton this weekend so I have to finish some errands in the city," he once said. "My Porsche is in the shop, so I have to drive the BMW up there."
Eventually, he decided to just go for it.
"I got an enormous bonus this year."
I waited for more, but that was it, so I said, "That's great, congratulations!"
He wasn't dumb, he just seemed sort of simple in his rich-person hang-ups.
He appeared to fit the usual profile until, toward the end of his meal — which consisted mostly of Glenlivet on the rocks — things took a turn for the unusual.
"Do you want to play a game?" he asked as I cleared his half-eaten shrimp, bruschetta, and mostly untouched arugula salad. It was a meal he'd insisted that I choose for him (this should have been my first clue) and then apparently didn't enjoy.
"What kind of a game?" I asked, smiling, balancing one plate delicately atop another, trying not to get tomato sauce on my sleeve.
"It's called 'Who's the Boss,'" he said, straight-faced. He was serious. "It's simple. Here, let me go first. Who's the boss?" I waited in silence.
"Well?" I asked.
"No, you tell me — who's the boss?"
"Um…." I looked around, wondering if I should just laugh and walk away. Act dumb or make it clear — somehow, in one clean gesture — that I am not to be messed with. But I was curious. "….You are?" I suggested. The customer is always right, right?
"That's not the answer I was hoping for," he said. "I like a powerful woman. Tell me you're the boss."
"I'm the boss?" I said, incredulous. And so it began.
Steve started coming in regularly, once or twice a week. He got drunk while I asked him about the women from other restaurants with whom he played The Game. He, in return, asked me what I was writing and my favorite books — then interrupted to tell me, as many men have, that I just have to read Hunter S. Thompson.
I asked him questions with genuine bemusement and a feeling of superiority.
The Game was that Steve took women to dinner after their shifts (I had an open invitation, he made clear). The woman he'd been taking out for five years, one of the original players, helped him conceive of The Game, which consisted of verbally bossing Steve around — from ordering him to hypothetically wash the dishes to requiring him to actually kneel down and beg forgiveness for some transgression. One player he'd temporarily "housed" (his word) successfully ordered him to pay her clothes, her phone, Prada sunglasses, and Marc Jacobs bags, until Steve's Jungian analyst, Hilda, implied he "had to give her up."
Hilda had some theories about the archetypes that explained Steve's submissive fantasies, though Steve — intentionally, it seemed — didn't share the specifics. To me, Hilda was the most fascinating character of all.
"It's worthy of note, Steven, that you also pay me to talk to you for an hour each week," she'd recently said. Naturally this gave Steve ideas.
Steve paid women in exchange for participation in his game. A kind of escort service incubated, for the most part, in bars and restaurants, with large tips and gifts as reward for verbal stimulation. Some will think I'm naive, but I believe The Game was actually the main event for him.
"Oh, I've scared you," Steve said a couple of times as he told me one anecdote or another.
"No, I'm fine," I replied, truly interested.
I'd often thought waitressing was a performance. Working for tips can mean smiling when you feel like shooting daggers, not laughing in someone's face when it's absolutely warranted, or simply being "on" when you'd rather be reading or taking a bath. Steve came in with unusual specifications to the job description — and additional rewards. He wanted to play at dominance and submission, and I wanted to make as much money as I could without doing anything that I didn't feel good about.