I started internet dating back in its very early days. It was more like proto-internet dating before the widespread use of websites, apps, and cell phones. I think the timing may have been just after the discovery of fire, or it may seem so to the tech-savvy youth of today.
As a thirtysomething Midwesterner, I had arrived in New York City in 1996 and wanted to meet women. But I had an appalling lack of pick-up skills and bravery, even at a bar with some liquid courage in me. Match.com was still in its infancy, so I tried “The Right Stuff,” a dating program which used the U.S. Postal Service.
I wrote a check for my $20 enrollment fee and created a brief description about myself using no more than 250 characters:
33-year-old, 5’8”, 150-pound white male businessman from the Midwest. New to NYC. Friends claim I have boyish good looks. Looking for someone to share some mutual interests including biking, movies, international travel, and exploring the city.
Karen, a platonic friend, offered to review my description. She said, “It’s mostly good. But you really have to cut that stuff about ‘boyish good looks.’ Women want a man, not a boy.”
I screamed “Ouch!” inside but maintained an exterior smile as I thankfully adjusted my blurb. I carefully added two more things to the enrollment package: a one-page bio and 20 headshot photos. The one-pager and a headshot would be sent to any woman who read my 250-character description and paid $2 to learn more.
Two weeks later – that’s right, weeks, not seconds – I received all the women’s two-sentence descriptions. They came on twenty pages of beige, xeroxed paper in a large manila envelope. I felt excited, overwhelmed, and even a little guilty. Suddenly, I had x-ray-like vision and could see detailed information on hundreds of available women. The White-Pages phone book would never be the same.
At first, I did not know what to do with all the choices. How would I select a few women to date from the hundreds of names? That’s when I learned a lesson, a somewhat bad lesson, about the power of what was to become Internet dating: I could be extremely picky.
Previously, I was content to meet any woman in her 20s or 30s who had at least a few years of college. Now, I could precisely target women ages 28 to 35 who were under 5’5”, had at least a bachelor’s degree, and shared several of my hobbies.
I selected five women, based on some combination of analysis and hope. For example, one woman had a dog, so I surmised she was warm and fun. I carefully wrote down each woman’s anonymous reference number on my response sheet, which I returned with the $2 fee per name.
Two weeks later, I received the full-page descriptions written by each woman, along with her phone number (landline) and photo. As I reviewed the seemingly confidential write-ups, I jumped when my desk phone rang. I felt caught like a voyeur. My reaction seems quaint now, but at the time, people had not yet unleashed their torrent of personal information on social media and dating sites.
After reviewing the potential women, I acted gallantly and chose just one to call–Marion. I would be two-timing if I contacted two women. Marion had the best smile – warm yet alluring. Given her master’s degree in French literature, I figured she must be well-cultured and smart.
Back then, calling a woman usually meant leaving a message on her answering machine, especially if you strategically called her home number when she was likely at work. After the beep, I spoke my mostly memorized speech, trying to sound confident and intelligent and fun, but not too confident or too intelligent or too fun:
“Hi, um, I’m leaving a message for Marion. This is Scott from The Right Stuff, that, um, dating service. I really enjoyed reading your profile. Perhaps we could have, ah, lunch sometime? I’m number 3454 on the Right Stuff list if you want to read my bio. We seem to have a lot in common. My phone number is 212-204-7754, if you’re interested. “
The next day, hallelujah! Marion left a message on my answering machine that she wanted to meet. My first date in the brave new world was set.
Upon meeting Marion in person, I learned another important lesson, which would apply to internet dating—do not trust the photos. On entering the restaurant, I searched the room for Marion, pausing at one point to smile back at a pleasant older woman who had smiled at me. My stomach clenched when I realized this “older” woman was Marion, dressed in a conservative, black floral blouse with a lace collar buttoned up to the very top.
Fighting back my concern, I slipped into auto-drive as I greeted her with a friendly hello and began a pleasant conversation. As we talked about our week, Marion’s personality showed that it was just as conservative as her dress. She told dry stories about her job as an assistant editor at a publishing company, her favorite authors, and even more stories about books.
I was struck by how different we were and how there was no chemistry. I suddenly remembered Susan, the woman who did not return my call after our date the previous month. She must have felt the same way toward me. I understood and forgave her. Feeling a little bad about myself for having been the object of such rejection, I now felt empathy for Marion.
Marion asked, “Have you read any good books lately?”
The prior week, very out of character, I had picked up an old novel from a sale rack at the mammoth Strand bookstore. I said, “A book by Balzac. I think it’s pronounced something like Eugene Grand.” Marion’s flat affect transformed. She gushed, “Oh, you mean ‘Eugenie Grandet!’ My master’s thesis was on that book!”
Marion had found some chemistry. Meanwhile, I wanted to find the check.
How could I be a gentleman and extract myself from the situation without hurting her? I continued as a pleasant and attentive conversationalist, which felt appropriate. As we parted, Marion said, “I hope to see you again.”
I replied with the kindest words I could truthfully summon, “It was a pleasure to meet you.”
After the date, I asked Karen, my friend, for advice. She told me, “You can’t avoid a little pain in such situations. Marion probably hopes you’ll call, but she’ll get over it in a few days. You were right to be honest. I hate jerky guy who says they’ll call but never do.”
I had entered the quite different world of what would become Internet dating with its seemingly unlimited choices and in-person surprises. At least, I would no longer have to make a fool of myself in bars.
Yet, I realized some things would not change. The search for a soulmate would still seem like an almost quixotic quest at times. And we should treat each other with kindness along the way.
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This post is republished on medium.com.
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Photo credit: iStock
Amazing to think how quickly online dating changed. And changed us!