This is the 10th long-form article I’ve written for Cincinnati Magazine. The
first appeared in October 1990; it would be 25 years before they let me do a second. Maybe they got complaints after my debut because I’d accurately quoted someone who told me, “I always thought you were an asshole.” Perhaps that word had never appeared in the magazine.
Whatever the reason, the long delay didn’t bother me, because that first one helped find me a wife. Mary and I recently celebrated our 21st wedding anniversary. Funny story, how we met.
Things were different back in the Olden Days of the 1990s. I actually mailed the article to the magazine in a manila envelope covered with postage stamps; that’s how it was done then. In fact, the Cincinnati of that time—along with much of the whole world—is now so utterly extinct I must first pause and describe it for those who don’t remember.
It was a planet devoid of an internet and dependent on telephones strapped to walls, videos demanding to be rewound, and computers the size of microwave ovens. It was also a world where single adults looking for compatible partners depended on personal ads printed in newspapers and magazines. No apps, no photos, no swipes. Men and women, paying by the word, snail-mailed their cute profiles to a publication, which published them. Readers aroused by specific cute profiles sent their typed or hand-written responses to a unique mailbox number at the publication, which forwarded the responses back to the cute profilers, who would then decide which of their newfound stalkers to contact directly. With everything happening via the U.S. Post Office, placing an ad meant the process of actually meeting someone could take a week or longer. A monthly publication—this one, for instance—slowed things down even more, but at least you then had a chance to get down to the weight you’d lied about in your ad.
My 1990 article was about that world, sharing the story of my own responses to several Cincinnati Magazine personal ads and the hilarity that ensued. After reading the personals, I chose 11 ads to respond to. But instead of writing to each woman individually, I tried a method that seemed much more interesting and clever. Clever, after all, was my professional calling card—I was on Cincinnati’s top-rated radio station. I had even been included in an earlier cover story in this magazine about Cincinnati’s funniest people. Clever was almost a requirement.
And so I carefully scissored out my chosen ads, pasted them vertically several inches apart on sheets of paper, typed a personal response in the space under each one, made copies of everything, and mailed out 11 packages that shared all of my responses with everyone. This innovative idea, I told myself, would provide a more well-rounded image of Jay Gilbert than any single response. And, of course, it would make me look cool.
Perhaps that’s why Cincinnati Magazine, in deciding to print my article, titled it “Personal Worst: a truly stupid way of responding to the Personals.” The results of my experiment weren’t disastrous, but neither were they successful. I got three responses. One turned into a lunch and an awkward date. The end. The second resulted in something like an actual relationship, but not for long. The end. The third, well, that was only an unsigned letter. I didn’t keep it, but as best as I can remember, it read, “I always thought you were an asshole when I heard you on the radio, but not until I received your letter did I realize that you were the asshole by which all other assholes are measured.” The end, including of my publishing career for a quarter-century.
And then along came Mary, the woman I married. Don’t misunderstand—she hadn’t written any of the ads I responded to. In fact, we didn’t meet for another three years. But she did read my article, and that played a role in our eventually getting together. Before I describe how that happened, I must explain a few more things about myself that I’ve thus far avoided.
I was not just a la-de-da single guy looking for new relationships. I was a recently divorced father of two, going crazy. The divorce had been amicable, but anyone who’s been through even the smoothest of these things knows how hard it is to recalibrate a social life. Especially a romantic one. I’d started by checking off the standard boxes of second-singlehood: jumping back in too soon, too clumsily and discovering how powerful my inner ninth-grader still was. Answering these magazine ads was going to be, I thought, a step in a more mature direction. Ha ha ha.
At this point in our story, it’s time for Mary to butt in:
My first marriage was typical for the era, happening before either of us had entered the real workforce. After five relocation “career opportunities,” it finally dawned on me that only his job could make him happy.
I had listened to the WEBN Dawn Patrol and to Jay during afternoons for years. When I read his article in the magazine, I thought, Why am I still married when there are guys like this out there, more alive and funny and engaging? The article was not the trigger that made me decide to end my marriage—that happened later—but it was a nudge, and probably a factor in my speaking up when I got a chance to meet Jay.
On a Sunday afternoon in 1993, I went with a friend to a small party, just a group of about 10 people, most of whom I didn’t know. In the middle of everything, I heard someone—let’s call her Sarah—mention Jay’s name. Oh, I thought, here’s someone who actually knows him. I joined the conversation and told Sarah I’d always wanted to meet that guy. Is he single? He doesn’t smoke, does he? Good. Then Sarah smiled and said, “Tell you what. He lives around here. I’ll go get him.” And she left!
I was home. The kids were over at the ex’s. Can’t say I remember what was on the TV, but chances are that I simultaneously had the 56k modem dialed into America Online: SCREEE-KGURRRRKK-SQUIAAA-KPT!! Welcome! You’ve got…
The doorbell rang. Probably someone selling magazine subscriptions. Why, no, it was Let’s Call Her Sarah, whom I hadn’t seen in a while. “Hi,” she said, “whatcha doing?” “Nothing, really. How are you?” “Fine, but I want you to come with me to a party. Like, right now.” “Uh, OK.”
On the way, Sarah said it was a fun party and she’d thought of me, but she said nothing about Mary. Here’s the thing about Sarah, which I should have remembered: One of her favorite pastimes was playing matchmaker. In a minute you’ll see how dedicated she was in that department.
I have only a vague memory of meeting Mary; she was one of several people I was introduced to, and we spent some of the party in one-to-one conversation. About an hour later, Sarah said she had to go pick up her kids, so hey, Mary, how about you take Jay home? Smooth move, Sarah. Mary said sure, and we enjoyed the short drive.
Don’t assume that the above examples of Sarah’s sly efforts are what I mean when I say how “dedicated” she was to matchmaking. You have no idea. Consider this: You know the melody to Wagner’s “Here Comes the Bride,” right? It has no original lyrics, but if you were going to write down the sounds you’d sing, it would probably look like this: Dumm-dunt-di-DAAA! Dumm-dunt-di-DAAA! OK, hold that thought.
A few days after the party, Sarah phoned to say she was having her own party the following weekend, and I was invited…but only if I brought Mary as my date. And by the way, here was her phone number. So I called Mary, and after sharing a good laugh about Sarah we agreed to attend the party. I picked her up a few days later. We parked near the party, and as we walked up to the house we saw Sarah and several other people out on the porch. When Sarah saw us, she instantly stood and, with a smile, sang in full voice: Dumm-dunt-di-DAAA! Dumm-dunt-di-DAAA! I was a little disappointed that she hadn’t booked some small children to scatter rose petals.
What can I say? It all worked. Mary and I kept seeing each other, and we got married in 1997. We certainly have Sarah to thank, but also Cincinnati Magazine for providing an invisible spark early on. Slow-burning printed personal ads of the past have been replaced with today’s mobile app firecrackers. Good luck with those, everybody. Just be careful, and watch out for the assholes.