What Happened When One Woman Dedicated Herself To One Full Year Of Online Dating

It was one of my first online dates. We were slogging through the early stages of an awkward conversation over coffee; I confessed that I was new to this process and wasn’t very good at it. “If I ever get good at this,” the guy replied, “it’ll be time to give it up.”

It was late autumn in 2003. At 37, I found myself single again after the demise of a seven-year relationship, and the possibilities of Internet dating seemed infinite. I was captivated by the idea that I could post a profile of myself for anyone in the world to see, that I could forge a textured relationship with someone before we had even met.

I had never “dated” before. In college, I’d fallen in love with a classmate the first day I arrived on campus and then spent the next four years obsessed with the ideal of that relationship (despite all evidence that “ideal” was all it would ever be).

In my twenties, I fell into several short-term relationships with friends and colleagues, but never went on a blind date and never perused the personals, even as an anthropological curiosity. At 30, I met a man through work. Two years later we moved in together. Three years later we had a baby together. One year later we broke up.

During this time, the Internet went from being a glimmer in Al Gore’s eye to an ordinary fact of life.

For a few weeks, I perused the Nerve.com online personals — back when there were Nerve.com personals — from a voyeuristic distance. I became intrigued by the profile prompts (“Most humbling moment.” “Five items you can’t live without.”) and began to imagine what kind of self-portrait I could craft for an entire world of potential soul mates.

When I came across a man I was attracted to, I decided to create my profile in earnest. I checked off all the little boxes: “never” smoke, “sometimes” drink, “never” use drugs. Interested in a “serious relationship” with a man who “never” smokes, “sometimes” drinks, and “never” uses drugs. I talked about my love of tennis and the streets of Rome; I mentioned my “adorable 2-year-old daughter,” whose birth was my “most humbling moment.”

When the time came to upload a photo, I was dismayed by my options. Most of the digital pictures I had of myself had been taken in the beleaguered days following the birth of my daughter and featured an alarming amount of unkempt hair and unbuttoned blouses.

Recalling the old adage about never getting a second chance to make a first impression, I washed my hair, applied a bit more makeup than usual, and went to the Kmart photo booth, where I sat for 20 minutes looking slyly into the camera in a way that I would never have been able to for an actual photographer. Finally, I bought a flatbed scanner to upload my new photos. ($79 seemed like a small price to pay for finding true love.)

And then I took the plunge. I contacted the man whose profile had attracted me, a great-looking architect who “couldn’t live without” his two kids and The New York Times. “Well, here goes,” I wrote, making sure he understood how new I was to this. I complimented him on his “flair for syntax” and closed by saying, “If, for whatever reason, I don’t hear from you, no hard feelings, and best of luck with all this.”

I didn’t hear from him.

If we applied the rules of acceptable online personal etiquette to three-dimensional behavior, the world would be a rude and confusing place. Imagine walking up to someone in a bar, or at your local gym, saying hello to them, then having them look you up and down, turn their back on you and start talking to someone else.

Of the 19 men I contacted over the course of the past year, eight of them simply didn’t respond to my messages. At first, it was hard not to take the rejections personally. But as I gained more experience and the tables began to turn (of the 135 men who contacted me, I simply didn’t respond to 90 of them), I came to understand that the reasons for ignoring someone online range from non-attraction to just being too busy to take down an outdated profile.

I didn’t disdain any of the men I ignored; I simply didn’t feel that elusive two-dimensional spark. And given the choice between sending a polite rejection letter and simply not responding, the latter seemed like the more sensible thing to do.

Over the next few months, I went on seven first dates that went nowhere fast.

I received four “winks.” I ignored six men. Four men ignored me. Then, as winter gave way to a glorious spring, I experienced my first sustained epistolary romance. I received a lovely note from a fellow writer. Within nine days we had exchanged 57 emails.

Letters have always been my preferred literary form. As a reader, I’ve gobbled up numerous collections, from Jack Henry Abbott’s letters to Norman Mailer, to The Letters of Kingsley Amis, to the legendary courtship of Robert Browning and Elizabeth Barrett. As a writer, some of my best work is nestled within the hundreds of letters I’ve written over the years to my teachers and friends.

Freed from the constraints of narrative structure, letters are places where we can experiment with our writing styles, make passing cultural observations, and record personal thoughts without regard for a wide readership.

The sheer volume of the correspondence between Barrett and Browning was inspiring to me when I first signed up for online dating. Over the course of a 20-month courtship, these two poets exchanged 574 letters. (The Victorian penny post was remarkably efficient, creating an effect not unlike modern-day email, with one to three exchanges taking place on a daily basis.) Barrett and Browning corresponded for four months before they ever met.

Their intimate, detailed letters created a deep and abiding love that was impervious to the obstacles the couple might face in reality. The writer I began corresponding with was newer to the personals than I was. He was protective of his anonymity and interested in exploring the medium for as long as possible.

“I can’t quite resist the possibility of meeting first this way,” he wrote. “The first time I see you, I’ll already know something about you that everybody doesn’t, and you about me. The dramatic possibilities are infinite.” I couldn’t have agreed more. For three weeks we kept our correspondence confined to Nerve’s anonymous little message boxes.

The letters became intimate and erotic.

When we finally met for a drink, I was surprised to discover that, although we had such a consummate connection on the page, there was no chemistry between us. Later he would explain, “It was easier to indulge in all those sexy fantasies as long as you were abstract.

But when you no longer were, it made me uncomfortable.” For my part, I was willing to give chemistry a chance; his literary persona had endeared him to me. But his position was clear: “I’d like to be friends, whatever that means — but not if it will raise your hopes about something else happening.” I told him it would probably be too hard to squeeze in a new friendship at my age, but thanked him for “raising the bar.”

Despite the fact that my profile specified that I was looking for a serious relationship with someone who lived within five miles of my zip code, I soon fell into a heated, erotic correspondence with a man who lived 3,591 miles away — an American-born journalist living in Spain. After two weeks of regular emails in which we shared our personal histories and love of good grammar, we turned our attention to sexual fantasies.

There was something about the forbidden quality of the relationship — the fact that we knew we couldn’t be together — that made these letters, especially arousing. Our inboxes became intensely intimate spaces. When he suddenly announced that he was coming to New York on a business trip, I was excited by the idea of meeting someone who knew exactly, in detail, what I desired.

When we met at his hotel, I immediately knew that I wasn’t attracted to him.

As we sat in the lobby bar trying to gloss over reality with a few stiff drinks, he suddenly seemed like the stranger he actually was. I replayed scenes and sentiments from our 78 emails, trying to remind myself why I trusted him.

Despite our obvious lack of chemistry, the idea of acting out our sexual fantasies was irresistible. We proceeded to his 40th-floor hotel aerie to play out an awkward reenactment of some of our more memorable email moments.

Looking through the room’s rain-streaked windows, I became entranced by a blinking neon sign glowing from a building two blocks away. The view provided one of those rarefied New York perspectives one is seldom privy to. I was grateful, at least, for that.

The driving rains of spring gave over to the dog days of summer. My attire became skimpier and my expectations more relaxed. When I met a sexy economist who said he was attracted to me but not interested in “seriously relating,” I realized that I was not as adverse to “play” as I had previously assumed.

In May I had turned 38 and soon my “adorable 2-year-old daughter” would become my “adorable 3-year-old daughter.” I realized that I was in the catbird seat: I had acted on my overwhelming procreative urge in my mid-thirties. If I fell into a serious relationship, there was still time to have another child. If I didn’t, that would be OK too. I arranged a play date for my daughter and then went out to meet the economist for a “play” date.

On a chilly late autumn night, with the one-year anniversary of my foray into Internet dating looming large, the two-and three-dimensional worlds finally seemed to come together. Three weeks earlier, I had begun a correspondence with a painter whose letter writing was spectacular (we exchanged 110 emails in three weeks — a record). In-person, the physical attraction was undeniable; there had even been sparks on the tennis court. On our third date, we met at a dark romantic lounge, where our unrestrained mutual lust almost got us arrested.

The next day he backpedaled. “I’m afraid I have to put things in a holding pattern,” were the actual words of email number 111 — words that sent me reeling away from my computer and into a fetal position on the bed, unable to believe that our relationship would not be moving forward. “The events of the past three weeks are swirling about,” he wrote. “I want to let them settle before I move.”

“Dear Whoever You Are,” I wanted to respond. “What have you done with the man I was with last night? The one who made me promise that I would make love to him within the next 24 hours? The one who was felled by my ‘defenseless eyes and reluctant smile’? Where are you holding that man? I’ll negotiate his release.”

Instead, I dug my own grave. I peeled myself off the bed and composed email number 112.

“Dearest S.,” I wrote, “I’d be lying if I said I wasn’t devastated.” Instead of playing it cool, I came totally clean.

I sent two more similar emails into the irretrievable realm of his inbox before I realized he wasn’t going to respond. (Perhaps he had decided that silence was the most gracious option.) That week, I was forced to acknowledge that, although he’d revealed a lot about himself in his 60 emails, there was obviously much more that he hadn’t. I also learned that I was hopelessly incapable of reading between the lines.

Long came Winter again and with it a comfort level that made me a bit, well, uncomfortable. I had come far enough in my epistolary output (432 emails) that I was finally beginning to run out of literary steam. I began to self-plagiarize, pasting descriptions of myself from old emails into new ones. (To my credit, I was often upfront about it.)

My literary flair still seemed to be effective, but I was starting to feel ashamed of my Internet persona— the one that was clinging so tenaciously to the possibilities of this realm, despite all evidence that a fantasy is just that. After all this time, I no longer felt that giddy knot of expectation in my stomach at the sight of a new message in my inbox.

A few weeks after my one-year anniversary, I received a note from a photographer who’d recently found himself single after two long-term relationships. I was the first woman he’d contacted through the personals. After a few spotty emails, he chose to call me. “I’m really not good at email,” he said. “I’m more of a talker.”

“Fair enough,” I told him.

“I’ve never done this before,” he said. “I’m not very good at it.”

“When you become good at it,” I said, “it’ll probably be time to give it up.”

The next day, I gave it up