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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. 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 online 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.