Dating Disasters, Part 1

by Simone Westfall — May 15, 2007

I have been, in my post-divorce careers, a vocation of approximately 10 years' standing, one of the champion daters of all time. Though there were a few so-called relationships along the way, lasting anywhere from six months to three years, vast stretches of wasted time were given over to drinks or dinner or one-night stands with men who were either totally inappropriate or not good "keeper" material for one damn reason or another. Since the advent of email and online dating sites, the exchanges in cyberspace that either led to a real encounter or simply fueled my down time with trading bits and pieces of information could easily fill a small volume with idle chatter (where did all those emails go? I sometimes wonder. Are they circling around Mars?)

Friends often ask me, What's the worst date you've ever had? But there were so many! Allow me, though, to draw from the recesses of deepest memory some real howlers. A few stick out like rusty springs poking from a stained mattress tossed out on the streets (which is a little like how I felt in the aftermath of divorce). And these are the ones I will recount for you over the next few days.

Long ago, in the days before Internet matchmaking sites, people turned to the personals in the back of magazines like New York and The New York Review of Books. One candidate who caught my eye posted an ad in New York: a surgeon in Nyack, just north of the city, who claimed to own a red Porsche and indulged a "serious" fondness for art. This captured my interest because I was at the time an editor for an art magazine. To my surprise, he responded to my response. We chatted on the phone for about 20 minutes; he told me he owned prints by Barnett Newman, Frank Stella, and Cy Twombly--all biggies in the art world; he sounded sane and smart. We made a date for dinner the following week at a restaurant on the Upper East Side (this was before I had made the drinks-first rule, which, as we know by now, I break all the time).

Bill showed up a few minutes after I arrived. Tall, as advertised, not truly "handsome," as he had also advertised (virtually all men, I have subsequently discovered, believe they are on some level "handsome"), but appealing in a George C. Scott kind of way: craggy face, wolfish grin, shambling walk. After we got through the pleasantries, he told me about his specialty in laser surgery. But his biggest passions, he said, were for golf and tennis. I swallowed hard and hoped he wouldn't ask if I played either. (I went to a private school in Manhattan. The only competitive sport I learned was shopping in Bergdorf's. I wasn't very good at it.)

"Tell me about your art collection," I urged.

"Oh, yeah. That. Well, I'm into prints, but my favorite thing is a little sculpture by Erté."

Erté, in my book, is a slick, kitschy Art Deco designer who belongs in thrift shops or Las Vegas hotel rooms.

"It's a naked girl in the shape of an L, for L___." He gave his last name. "Her legs are up in the air and she's lying on her back. Really sexy."

It was at this point that I began to notice that Bill had a very loud voice, which carried even above the din of the restaurant. A couple of diners turned to stare. I buried myself in the menu.

Eventually we moved on to the subject of former partners. His second wife of eleven years had left him six months earlier. "But we had a fabulous sex life right up to the end. One night a week was for her, one night was for me, and one night was for the both of us."

More heads turned in our direction. I ordered a second glass of wine, still wondering about this equation, especially "the both of us."

"Why did she leave?" I asked.

"I dunno." He shook his big George C. Scott head, which was getting less appealing by the moment. "She got itchy. That time of life, I think." He played with his fork and then bellowed, "You know, I've reached the point where I just won't go out with a woman older than forty-five. Ever. I can't go through that menopause shit again."

By this point, I just wanted to suffer through dinner and get home to my dog. But I was grateful that I was about five years away from his threshold, both golf- and tennis-challenged, and in a restaurant to which I had no desire to return.

Grateful, too, that he apparently had no interest in me. But I did get a ride home in his nifty red Porsche.

Simone Westfall is the pen name of a novelist and critic in New York City. To read all of Simone's posts in "The Dating Life," click here.