Striking the right key on New Year’s Eve, 1999. (Photo by Adrian via Pixabay)

As the last days of the year 1999 counted down to the 21st Century, we were all wondering how this landmark New Year’s Eve would play out. The big question was what might happen to our personal computers and the data they carried?

As the clock hands moved from the 20th to the 21st Century, Cupid -- disguised as the Y2K Bug -- played his own hand.

Would they become high-tech pumpkins?

Y2K issue

This fear that settled over the world had some merit to it, and it was called the “Y2K Problem.” The concern was of  potential computer errors related to the formatting and storage of calendar data for dates in and after the year 2000.

Many computer programs represented four-digit years with only the final two digits, making the year 2000 indistinguishable from 1900. Computer systems’ inability to distinguish data correctly had the potential to bring down worldwide infrastructures for industries ranging from banking to air travel. In the case of me and my university colleagues, all our stored research and class notes were at stake.

What might happen to all that data? Would the changeover to the 2000s scramble our stored data? Make it inaccessible?  Would there be a loud pop at midnight coming from inside our desktops, followed by a plume of smoke coming out the ventilator slits?

All of the above? None of the above?

Faculty on guard

At the University of Memphis, we faculty were advised to back up computer data and monitor our computers on the night of Dec. 31, looking for signs of damage caused by the sweep of the clock’s minute hand past midnight 2000.

Since I was single and my love life was drowning in the tank,  I had no plans on New Year’s Eve, so I spent the night in my office — probably the only one in my building to do so — and babysat my desktop Mac. Happily, the night passed safely for it and my data.

No smoke

I breathed a sigh of relief when the clock struck 12 and my computer failed to explode. Indeed, it just sat there and looked at me like I was an idiot for camping out in my office instead of going out and partying.

What I didn’t know was that Cupid was right there with me. At 12:05 a.m., he reached over and flipped up my AOL flag alerting me that, “You’ve got mail!”

Who, I wondered, would be writing me just after midnight on New Year’s Eve? Could there be someone else as foolish as me at the university who was nursing their own computer in their office and saw the light from mine through the window?

I clicked the message open and was surprised to find a mystery woman had written me, telling me she loves to bake chocolate chip cookies and believes them to be the best in the country. Quickly I realized she was responding to my “must love dogs” post on the One and Only dating site, wherein I had mentioned I love chocolate chip cookies.

A surprise date

Wow, I thought. Looks like I have a date on New Year’s Eve after all! Her name was Anne, she lived one state over, in Kentucky, and she had found my profile interesting enough to write and say hi.

She liked the fact I was a journalist and an educator, she joked about my references to my world travel and to the fact I actually had an Indiana Jones snap-brim fedora hat. She said any man who seemed that rugged, had a Ph.D, and yet still had a soft spot for chocolate chip cookies must be okay.

Anne did not post a profile picture, which usually lessens the chance for a response on dating sites. But she seemed so sweet and clever that I wasted no time in responding.

“So, your bakery must be open all night,” I wrote. “Since I live in Memphis, it’s unlikely I can swing by to sample your cookies, but maybe we can talk awhile online, anyway. Are you up for that?”

Taking it slow

So, yeah, we did talk more. A lot more. And, for the first time in a long time, I was actually thinking something was going right in my life; something which I absolutely did not deserve. But I resolved I would gladly take it, anyway.

Annie and her dad Chuck.

A couple days later she did send me her photo, and she was as pretty as her online personality predicted she would be. The photo showed her dancing with her father (who bore a striking resemblance to Jimmy Carter) at her daughter Mollye’s wedding. She had a smile that brightened up the dance floor, and I predicted – correctly, as it turned out – that Anne and I would be talking a lot more.

A song in her heart

She told me she was a musician, with degrees from the University of Kentucky, and that she was performing with her local community theater and was about to play the role of Miss Hannigan in Annie (obviously against type for such a pretty actress). She was recently divorced and had three daughters.

I wasted no time in responding and telling her about my two sons.

The month of January passed, and I felt a new breeze blowing through my daily life. I was buoyed by the possibility that Anne represented. I was actually happy for a change.

Reading the tea leaves

About a month into our online exchanges, Anne and I felt confident enough to set up an in-person Kentucky meeting in Lexington, not far from her home in Winchester. We agreed to meet at a wonderful bookstore called Joseph Beth which had a pleasant café’ on its first floor.

We set the meeting for the night of Feb. 14. Valentine’s Day seemed appropriate. I arrived about 6 p.m., and Anne was already there. I had written her I’d be wearing a burnt orange barn coat, and when she spotted me, she came to the front of the café to greet me, holding out her hand. We shook and she took me back to our table.

I cannot remember what we ate, but I will always remember feeling so comfortable talking with her. She spoke of her daughters, her community theater work, and of what it was like growing up in Kentucky. She was a very young-looking 47 and I was surprised to find her oldest daughter had already graduated from college.

She was very self-possessed, independent, and secure in her womanhood. She was also straightforward and, she had already let me know in an email what she would like the ground rules to be of our face-to-face meeting.

“Jim,” she had written, “I look forward to meeting you in person but, in case we don’t feel a connection, let’s have an understanding that we chalk our meeting up to a nice dinner conversation and then go our own ways in life.”

No Jolene

Wow! I thought, as the relief flowed through me. This is not going to be another Nashville experience with a desperate woman we’ll call Jolene who tried (unsuccessfully) to trap me in her guest bedroom overnight by sleeping on the floor on the other side of the door I had locked firmly. But that’s another story.

This woman Anne does just fine on her own, I thought. Better than I’d been doing myself over the past four years in trying to pick up the pieces of a shattered dream.

Closing time

We talked about three hours straight, and the cafe’ was ready to close up.. So, we each paid our own check (another of her ground rules) and went into the lobby of the connected Hilton hotel where I was spending the night.

Our new relationship was off to a good start. I had learned years ago about the relative value of being able to converse easily and deeply with a woman instead of using dinner as a prelude to sex.

After another hour of talking, we said our goodbyes as I walked her to her car out in the parking lot, allowing ourselves to at least embrace in a good-night hug at her car. But she did invite me over to her home in nearby Winchester for breakfast the next morning. I readily accepted, she got into her car and I waved goodbye and walked back to my hotel.

This much I knew

As I reflected later on the evening, I realized two things: first, I liked Anne very much, and second, that while the idea of taking things slow was different for me, it was best if we did it that way.

Annie and me at Laguna Beach.

Neither of us was sure we’d found the one we’d been looking for, but we did sense that this was a promising relationship and we wanted to see each other again.

So that’s what we did. Again and again and again. Today, in fact, we’ve been seeing each other daily for 23 years as husband and wife.

Anne calls us pioneers from the early days of digital dating. I just call her my Millennial Woman.

Jim Willis
I am a writer, college professor, and author of several nonfiction books, including three on the decade of the 1960s. Several wonderful essays of gifted Retrospect authors appear in my book, "Daily Life in the 1960s."