By Ann Landi
When I first started dating again, in the mid-1990s, after the collapse of a 15-year marriage, the playing field was slightly different. The back pages of New York magazine were crammed with personals ads, which I sometimes studied furtively, even while wedded (didn’t everyone?), wondering sheepishly about greener pastures. But my first real experiences with the guys who took out classifieds were anything but a romp through sunny meadows. One fellow who claimed to look like Tom Brokaw (and he did) cried throughout dinner after describing his most recent breakup. Another who claimed to look like Harrison Ford (he did not) had a voice that carried to the far corners of the restaurant as he expounded on his sex life with his ex-wife (“One night was for her, one night was for me, and one was for the both of us.” Years later, I’m still wondering about that.)
After the date with the second, who at least drove me home in a nifty red Porsche, I called up my about-to-be ex-husband and vented my fury into his voice mail: “Of all the crappy things that happened during the course of our marriage, this is by far the worst. I can’t believe I have to go through this godawful hell of dating all over again.”
Nonetheless I did eventually settle into a four-year relationship with a nice-enough guy but by the time that ended, around the turn of the millennium, the ways in which romantic prospects could advertise their availability had gone through a sea change.
Online matchmaking sites were beginning to multiply with the ferocity of bunnies in the spring, and I entered this brave new world of dating with more dewy-eyed innocence than one should reasonably expect from a woman in her 40s. I signed on with Match.com, then and probably still the biggest meat market for hopeful singles, and posted a couple of fetching photos of myself as well as a write-up about all my fabulous qualities.
Within short order I was corresponding with a guy in Barbados who said he made frequent visits to New York. Winter was fast approaching. A long-distance romance with a man in the Caribbean sounded pretty appealing. He described himself, somewhat mysteriously, as a publisher of online business magazines. (I wasn’t smart enough yet to ask for links.) He looked buff and healthy in his photos, and he knew how to write in complete sentences, observing most if not all the rules of grammar, an endearing quality to a writer. We became quite chatty--all of it on email--about the future of publishing, print versus web.
I had tickets to see Tales of Hoffmann at the Met one Saturday afternoon in early December, and told Barbados Guy it was one of my favorite operas. He wanted to know what I planned to wear. It seemed a harmless enough request, and so I told him: high-heeled black boots, a dressy sweater and a long black skirt, a double-breasted wool coat with gold buttons. He didn’t ask for sleazy or intimate details like underwear. The production, with Ruth Anne Swenson and Bryn Terfel, was superlative. I walked home, happily humming “Elle a fuit, la torturella.” How cool it would be, I thought, if maybe Barbados Guy liked opera too. We could have drinks by his pool and crank up the volume on Fleming and Domingo.
I was delighted to find an email from him in my inbox when I returned home. Maybe he was reading my mind. “Forgive me,” he wrote. “But when I thought of you in your high-heeled boots and long black coat, I came all over my computer.”
My first thought was, Ew, gross. My second was, How could he do such a thing without frying his keyboard?
And there went all thoughts of a winter holiday in the Caribbean.
Such was my introduction to Internet dating, which has had its peaks and valleys ever since. I’ve learned a few things, had some dreadful encounters, and even enjoyed a couple of rewarding relationships via online matchmaking (though none, alas, has yet resulted in a second trip to the altar). Anyone venturing into the postmarital realm of midlife dating invariably winds up on the Web at some point, facing huge challenges. I hope my pratfalls and hard-won experience provide a few guidelines, or at least some amusing cautionary tales.
