Dating as a Single Dyke in My 60s

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’.”


“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.

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Elaine Bennett

Who I am: A queer woman writer living on the traditional land of the Wampanoag. Who I am NOT: the lady from Seinfeld (her last name was Benes).

Elaine has written 1 article for us.


  1. Elaine, your wit and charm are entirely delightful! I wish you the best in finding someone and hope to see more writing from you.

    Editors, huzzah for more older-straddler writing, thank you. :)

      • Please keep sharing your insights and your charm and wit on AS!

        Article ideas: how to wear a colorful schmatta for any occasion, Interviews with interesting people over fifty, intergenerational conversation with another AS writer, profile of magazines/media you’ve enjoyed in different decades, gay slang in different decades, quiz: which colorful schmatta are you?, or really anything on art, capitalism, retirement, golden years, friendship, intentional community…

      • updates on your match search – we’re invested now :)

        but also pieces like this one that look at what is with a lens of what was when we were the target demographic… like, i was talking to a youngster about music and mentioned CDs, and she thought those were even more ‘old school’ than mp3s (versus streaming). and sure, but then i ran through technologies i am older than cassettes, but not 8-tracks/reel-to-reel, vinyl obviously; personal computers; microwaves; DVRs/VCRs; cable tv… stories that have that kind of flavor.

        sorry if that’s a ramble, but i love it when AS does pieces wuth a then & now format.

  2. i’m not trying to meet anyone these days, but vicariously experiencing the process through a contemporary was, well i’m not sure what to say, maybe an amazing glance at the road not taken.

    rooting for you, Elaine. and hoping that trying all you can think of is supporting you the way it should.

    some enterprising straddler(s) could maybe setup a message board/Slack/Discord server, etc… for straddlers to chat with other straddlers looking for love/companionship?

    • I loved this. I’ve realised recently that dating in my thirties is harder than when I was still at university and everyone seemed to be single.

      I appreciate the wisdom that age doesn’t necessarily mean stability or maturity. And that self-esteem is important. Knowing that others also find dating hard is reassuring. Maybe there’s less to be scared of in knowing that.

      I look forward to reading more of your writing Elaine, and wish you all the best!

  3. Loved your writing and experience during different periods of time. I’m rooting for you. A friend recently told me that the love Story between Roxane Gay and Debbie Millman had made her wish for a movie adaptation of their romance (same).
    I am very happy AS is publishing your story.

  4. What a great read. Especially loved this line:
    “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.”

  5. This hit me in the feels more than I bargained.

    Sexagenarian here, now divorced after a long and arduous relationship. It was like coming out all over again, the world has changed so much, improved so much ! Nevertheless I do feel lost at sea most of the time. Am I Ace ? This is something that didn’t quite exist in my youth but if it had been more talked about, I might very well have had an epiphany.

    I’m not up to using dating apps, I was doing in-person meet-ups until lock-down, and lucky for me I built up a nice little support group that only got stronger during the pandemic.

    But I’ve seen how I react to intimacy, it’s laced with trauma.

    I feel safe having crushes though, because I have control. The furthest my heart will venture is to be “in like”.

    And that’s fine, keeping it light, lovely, without expectations.

    Thanks Elaine, for your writing and the subsequent soul-searching.

    • flirtationships are the best. lovely interactions without expectations, no worries about hurt feelings when it stops.

      i wonder if aging adds to the curiosity about ace. i don’t think that’s my thing, but i’ve thought about it, too. it’s been a while since i’ve felt the desire for a companion. commitment’s cool, but needing to be always present for someone else is a lot of energy i can’t really find currently. maybe historically. but also, i haven’t met anyone who could motivate the effort. and i’m pretty happy without. life is very full if you let it be and waiting around for someone else -for me- feels wasteful.

      the older you get, maybe the field narrows some in terms of the dating pool? i mean if one is looking for a contemporary. like, i wouldn’t be super into the idea of a thing with someone younger, though wouldn’t dismiss it as a possibility. the ability to relate temporally and experientially is more appealing. i feel like the quadragenarian+ set are less visible, but that could be me, since there seems to be a number of people commenting here on AS as genx+.

      it’s been lovely looking through/thinking about the comments/replies to this piece. thanks for a nice start to wednesday.

      • You’re welcome, Ms. A. I was briefly single in the ’90s and 2010s so didn’t have quite the same culture shock coming into the modern dating scene. I made a joke recently that maybe I should date someone younger who could care for me in my dotage and the next day one of the apps delivered me an 18-yo. I screamed, NOT WHAT I MEANT— and laughed so hard. I agree with you, there’s no point in waiting around for someone. Living my life and if I find someone who wants to live theirs alongside me, I’m open.

    • I am new to this site. And new to world of lesbian dating. I was in a relationship for a very long time–the house, the dog, my mother in law(who I adored)
      That ended very badly. Thats all I am going to say. I moved to FL. with her bc she said it would be a new start for us. It was total betrayal. I spent the last 4-1-2 years single. One date— what a nightmare. Then came Covid. After Covid not much changed except me. I decided I was not giving a place I hate another second of my life. So I moved back up North where I am from. I still have the villa in FL which is beautiful and on a real lake 60 feet deep not a FL mudhole.
      It’s going up for sale soon.

      How do you meet someone to love in this crazy world? I feel like a dinosaur. Yet I would like one last love before the big finale.
      Scared? Yes. Shaking in my Italian loafers? Yes. Hesitant? Definitely. I had cancelled all subscriptions to dating services 6 months ago.
      Last night I got an email from a dating service saying I had three interested woman. One woman had sent me several texts. I read her bio which seemed interesting until I came to the line ” I don’t date women in their 60’s or 70’s. (She was 70 and no Cate Blanchett) it went on ” Because they are usually fat, stupid, out of shape, and very boring” 50 years old is as old as I go” Stupid me…I wrote back ” Please stop texting me. I am 68. Too old for you. But I am not obese, stupid or boring.” Well I got back too scathing paragraphs–won’t into go into them. So I just blocked her and re-cancelled my subscription. Anyway, I don’t have any answers but I enjoyed reading your post. Glad to know there are others of us out there. Deb

  6. Elaine, you are a gem!! I absolutely adored reading about your romantic adventures over the years. Would love a dating diary as you get back out there post covid. Sounds like you’ve got a lot of new fans here hoping for more of your writing!

  7. I just saw this article thanks to the More, Please Newsletter. Such a good and fun read! Thank you! I’m 54 and sometimes I miss articles about us queers in the 50s and 60s or more. I hope we see more of your writing here. :)

    I share your experience with dating apps and, yes, always feel like throwing the phone away with all the cis men likes… :P I’m a widow and decided to start dating again as COVID hit, so dating apps were my only choice, but really not a fan.

    Best of luck to you!

  8. I am 59. I have no idea how to meet anyone, more or less women interested in women. I have no idea how to spot them. I had such horrific things happen on dating apps with men, I will not even give them a chance now, I tried some with women and it seemed the same as men, never met any females, just got off them and not interested in using them. There are no ‘bars’ or other such ‘places’ anywhere near me.
    I would rather just meet someone organically but do not see it happening. Unless they come up and kiss me, I am clueless.

    • OMG, Amlyn, I feel you. When I worked with a dating coach, her first questions was “Why do you think you’re having trouble finding a date?” and my answer was “Because there are no lesbians walking through my living room!”

      Go out and do something you enjoy — volunteering, activism, dancing — and you’ll at least have fun, whether or not you meet someone!

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