Back in the olden days — before the internet, I mean — I knew of only two ways to find a girlfriend: in person (at a bar or, during the ’80s, a disco) or by mail. If you were shy — and I was very, painfully, almost self-destructively shy — the first method didn’t work so well. The second cost a lot of money, especially for someone in an entry-level job: first to place a personal ad in the back of the newspaper and second to rent a mailbox at the publisher’s offices to receive the responses.
The divorced straight man I worked for had researched the personal ad process thoroughly. Following his lead, I scraped together enough to purchase the least expensive possible ad — three lines of tiny type — in the Personals section of The Village Voice, then a still-respected weekly publication. I also started answering ads, including one that said something like “GWF 32, Southerner transplanted to NYC, seeks GWF. Yankees okay.” She meant folks from the north, not from the baseball team. And note the ‘G’ — Gay. We adopted the acronym of our brothers. And the ‘W,’ well, that’s how those ads were in the ’80s.
The thing that really caught my eye was her age: 32. Nine years older than me! I’d had a bad experience with the last woman my own age I dated. Hours after our first hookup, she fled the city for a tiny town in the Rocky Mountains. Okay, it was weeks, not hours — but it felt abrupt and, although we never said the word, final. In a world before cell phones, long-distance calls cost big bucks. We exchanged a flurry of letters for six months or so, but things fizzled out. We wouldn’t see each other again for 25 years.
In any case, this Southern GWF — let’s call her Addie, after the way we met — she was in her thirties. Clearly by that advanced age, she’d be solid, settled, not the kind of person to spend the winter alone on a mountain tending llamas. About six months after I responded to her ad, my phone rang: Addie. I didn’t inquire about the time lag; maybe she was a slow reader. We met and started dating.
She had a little barbecue at her house on Long Island, just me and one of her friends. The friend was about to meet a woman she had contacted through a personal ad as well, and she was excited about the prospect. “She’s in her forties,” the friend said. “Forty-year-olds are so much more stable than people our age.” Oh shit, I thought. Within two weeks, my thirty-something girlfriend invited me to her house — to help her pack. My heart stopped. But she was just moving farther east on Long Island. A longer commute for me, but nothing like the Rocky Mountains.
Addie had barely unpacked in her new place when I got another call: “Ah’m movin’, darlin’.”
“Again?”
“Yep. Ah’m goin’ home t’Florida.” She left so quickly I don’t think we even got to say good-bye. So much for the stability of thirty-somethings.
As I learned, you can’t measure stability by age. Yes, we older folks are more likely to have mortgages and jobs that keep us rooted in place, although as work becomes more mobile, even that’s less of an anchor. If it’s maturity you’re looking for, stability is not a good proxy, but my twenty-something llama-tender and my thirty-something serial mover did have something in common: a lack of emotional commitment, specifically to me. I didn’t notice it at the time because, well, I thought that sort of thing only happened in rom-coms. I’d be as likely to find a unicorn strewing glitter all over my backyard.
That’s on me: clueless, boundary-less, twenty-something me. I thought what I needed more than anything else was a girlfriend, but I was wrong. What I needed more than anything else was self-esteem and maybe a vibrator. Those things will never leave you.
I did manage two long-term relationships — 10 years (personal ad) and 16 years (introduced in person by a mutual friend), respectively — but a brief and ill-considered marriage (dating app) left me single again. I don’t blame the app. I thought a 95% match was pretty good — that’s at least an A, right? — and it was based on science, not just on my often-fallible radar. Still, I didn’t recognize how many dangerous tendencies a person can pack into that remaining 5%. Once I did, I had no option but to bail.
If I thought it was hard to find women in my twenties and thirties, singlehood in my late fifties to early sixties feels like trying to climb a sheer mountain cliff armed with only a bottle of lube. The good news is that vibrator technology has improved significantly. Also good: I can meet potential dates (or at least see their pictures) whenever I pick up my smartphone. I’ve got all the apps corralled into one folder, which makes serial swiping much easier.
But no matter how many dating apps I join, my daily review never takes long. Whether because I live a couple of hours from the nearest big city or because my age starts with a scary number — or perhaps because my wit and charm don’t translate well in two dimensions — I receive far fewer likes than I bestow. In three years, dating apps have yielded only three real-life meetings. Only one of those progressed into dating, but it never turned to love. Six months later, I was single again. I took a year or so to heal and then I reinstalled the apps, refreshed my photos and limbered up my swiping finger.
Maybe I’m too picky. If there’s not at least one picture of you looking squarely in the camera lens — I’m swiping left! If your only picture is cleavage — breast or butt — left! If you’re a cis dude, I throw the phone across the room in disgust — I keep an empty place on my sofa just for that purpose — and then I swipe left.
In the summer of 2020, after several years of app-fueled frustration, I even hired a matchmaking service. If I’d had that kind of money back in the 1980s, I could have bought an entire issue of The Village Voice. But desperate times call for desperate measures, and the company guaranteed matches with three different compatible women. This company mostly handles straight relationships, but my personal matchmaker — being a fan of Fiddler on the Roof, I call her Yenta Debbie — assured me that she’d be able to find me a woman, no problem. She interviewed me on Zoom for about an hour, plugging in keywords like “smart” and “butch” into her computer search. The company’s database didn’t spit out too many matches on the first try, but Debbie assured me that she would search far and wide (within my geographical boundaries), even calling around her matchmaking network to search their databases. I gave her some comps — age-appropriate versions of Abby Wambach or Hannah Gadsby — and sent her on her way.
A few weeks later, she had a prospect! Debbie made the reservations, and my date and I each traveled about an hour to meet at an outdoor restaurant last October. I sat at the table in dangly earrings, my favorite bracelet, a colorful, flowing schmatta over my black T-shirt and pants, and tried to keep breathing. Then the door opened and a woman appeared wearing a broad smile — as well as dangly earrings, bracelets, and a colorful schmatta over black clothes. I tried to steer her mentally toward another table, but she sat down at mine. We were a great fit personality-wise, but clearly Yenta Debbie had a thing or two to learn about “butch.”
COVID heated up after that, and with no vaccine in sight, I put the matchmaking on pause. My Yenta’s back on the case for me now, though, so I’m hovering on the continuum somewhere between “you create your own reality” and “don’t get your hopes up.”
At least my vibrator still works.
