Loneliness, like a mangy vulture, turned in a slow, lazy circle above my Chicago life, always threatening to overwhelm me with its musty, oversized wings. I had two go-to strategies for keeping the vulture at bay. One, I could purchase a new video game—nothing lifted my spirits the way that breaking a $59.99 game out of plastic shrink-wrap did. Or, two, I could purchase a 12-pack from Lakeshore Liquors, and ramp up my beer intake. On an unseasonably warm evening in March, when neither of my go-to’s could stave off the vulture, I ventured into the unknown: a sex shop…

The employee locker room at the East River Club featured an overwhelming array of hygiene products including aftershave, two kinds of moisturizer, soaps, hair gels, deodorant, tonics, sprays, and colognes. All of these products, including the mouthwash, were a shade of faded green that reminded me of a wrinkled dollar bill that had been put through the wash. The products were manufactured by a company named “Clubman.” The Clubman label featured the silhouette of a dandy wearing a top hat and tails and leaning on a cane in a leisurely fashion. The implication was clear: If you used Clubman, no…

About a month after “Splash Dance,” as Reynaldo had dubbed my dousing of the Oprah doppleganger, just as I was starting to ease into a routine at the Club, Mr. Galanti hired a new waiter named Dave. Dave was tall with hair the texture and color of wood shavings and a mouth that seemed to be disproportionately small in relation to the rest of his face. He’d famously arrived for his initial interview at the East River Club on a skateboard. When Mr. Galanti introduced Dave as the staff’s newest addition, Dave gave a brief “funny” speech about himself. He…

My tray-carrying skills improved more quickly than anyone could have anticipated. Within days, I found myself traveling from one end of the restaurant to the other at full speed, feet churning under me, with a drinks-crammed tray borne aloft on my fingertips. Could I pull off a bottle of chablis and four wine glasses? Two bottles of cabernet and eight wine glasses? What about three bottles of zinfandel, eight wine glasses, and three Old Fashioneds? I discovered that I could do all of these things, and more. Even the way the glassware chattered next to my ear as I moved,…

The Oprah doppleganger wore a dramatic sweater-cloak type thing draped over her shoulders. It fastened at the throat with a button that was the size and shape of an iridescent drink coaster. The garment’s material was blindingly white and featured intricate patterns in the stitching. The patterns reminded me of a well-groomed ski resort, and I said as much. Both women laughed then congratulated me on my observation. I took their drink order and promised to return in two shakes. (more…)

For the first hour of the dinner shift I shadowed Reynaldo, always staying a few feet behind him, listening and watching him work. He was a master of his craft. First he’d welcome each new table to The Restaurant, then he’d compliment one of the people at the table, usually one of the men, who, to my surprise, would almost always respond by blushing. Then he’d take a drink order. He’d tell the table about the night’s specials, doing so with salesmanship and gusto. He’d say, “And that’s prepared with a whisper of cilantro and it’s $14.95.” The customers would…

The East River Club, like all country clubs, had a large number of rich and famous members, many of whom rarely ever set foot in The Club. The richer and more famous a member was, Reynaldo explained, the less he or she visited the place. Reynaldo pointed to the men and women milling about in the atrium dressed in yoga pants with towels over their shoulders. “The ones who come here every day,” he said, “are desperate to justify the insane membership fees.” The lone exception to this rule was Oprah Winfrey. There was no one in Chicago who was richer…

Dear Readers: My apologies to the handful of you who come to the site on a daily basis in search of an update. The reason I haven’t posted anything in weeks is simply this: I’ve been going through some personal b.s. lately, and that b.s. has made it extremely challenging for me to write. I know, I know—if I’m going to call myself a writer I should be writing, no matter what the emotional weather is, etc. etc. Well, for whatever reason, I can’t seem to get myself together enough to get a damn post out the door. On the…