People Thought I Was Ridiculous For Trying Online Dating In The 1960s, And Now It’s The Smartest Way To Meet Someone

Last updated on Feb 26, 2026

Vintage photo of woman in nineteen sixties. iofoto | Shutterstock
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In the 1960s, long before there was Match, eHarmony, Christian Mingle, or even personal computers, there was Operation Match — the first online dating service in New York City. When it made its debut in 1965, the point of Operation Match was to combine "the irrationality of two particular social evils: blind dates and mixers." 

It worked like this: You sent in three dollars, filled out a questionnaire, mailed it in, and then potential matches were chosen for you through a computer algorithm. Your matches would then be mailed back to you.

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People thought I was ridiculous for trying online dating in the 1960s, and now it's the smartest way to meet someone.

Curios vintage computer keyboard showing first online dating service Photo by Jason Leung on Unsplash

I was curious to see who I would be matched up with, so I decided to give Operation Match a try.

After filling out a lengthy multiple-choice questionnaire, I snail-mailed it with three dollars in exchange for the names and telephone numbers of three computer matches. I impatiently waited a month before the names of the men of my dreams arrived in the mail. I couldn't wait another minute, so I immediately phoned each one and set up times to meet.

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My first match was a better-than-average-looking Columbia University law student, and a few years older than me. We met at the women-only Barbizon Hotel, where I was living. Since men weren't permitted anywhere but the lobby or mezzanine, we found an area on the mezzanine where we could talk privately.

Our conversation was awkward right from the start, and we soon realized we had no rapport, and the date ended abruptly.

Crying woman showing realization first online date was awkward Stokkete via Shutterstock

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There were still two more guys to meet, though, so I held out hope. My second match picked me up on his motorcycle. He wasn't my type and was rather rough around the edges, but I was willing to give him a try.

I dressed the part in a black leather pantsuit for a dinner date and was freezing in nine-degree weather as I rode on the back of his motorcycle, forty blocks to Chinatown. Over dinner, he bragged nonstop about his druggie lifestyle. It was obvious we had nothing in common.

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I was anxious to get back to the warmth of my room at The Barbizon, and the motorcycle ride back seemed like an eternity. With only one more "match," my hope of finding Mr. Right via computer dating was starting to dwindle.

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After meeting the first two incompatible men, I wondered how they could have possibly been paired with me.

Not wanting to waste any more time on dates that didn't work out, I spoke on the telephone to the last guy for over two hours. We had a good connection, and his voice sounded alluring. We decided to meet that night at a bar around the corner from The Barbizon.

I took one of my girlfriends along for moral support. We sat at the bar so he could easily find us and waited just a short time before I heard someone call my name.

I turned around expecting to see Prince Charming; instead, I saw a man who resembled Clarabell the Clown with three clumps of red hair on his head — one clump on each side and another clump on top of his head; the rest of his head was bald. Shocked and disappointed, I quickly turned toward my friend and the two of us talked until we were certain he had left the bar.

That was the last time I had a computer act as a matchmaker for me, although I know things have improved dramatically with the creation of online dating.

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Modern online dating has become so much better than anything I tried in the 1960s, when it was a joke.

So when you're feeling demoralized by the prospect of online dating, just know: there is one good thing if you ever decide to give it a go: at least you won't be tricked into meeting someone without seeing their photos — unless that's what you want.

RELATED: Happiness Expert Says This Group Of People Is The Healthiest And Happiest Overall

Mel Currier is a contributor to YourTango who writes on love, relationships, and the early years of online dating. 

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