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Looking for Love

Updated: Feb 23, 2021

The COVID Granny Diaries

Looking for Love on Over-50 Dating Sites. A hilarious, scary, and humbling walk on the wild side of the final decline.

As a mother and grandmother, I look for Valentine’s wishes from my family. I have bought Liza, Caitlin, Scott, and Nova little trinkets and wrapped them up to look festive. Eliza is coming down from Boston (she is currently quarantined and tested) and we plan to celebrate by watching Sleepless in Seattle while eating ice cream.

But Valentine’s Day is really for lovers and, in that spirit, I have decided to share my recent experiences in online dating and hope you will be amused and sympathetic, rather than shocked and grossed out.

My house in February 2021.

My heart was broken when Jim and I parted five years ago. I was so devastated that it took me ages to accept it and let him go. I was left with scorched-earth emotions that would not let me consider letting another man in my life. During that time, I began seeing a wonderful therapist, and have now spent years raking over my “issues” and trying to heal. I rebuilt my life in a new town, got really lucky to have my family nearby, wrote a book, built a small consultancy, and acquired the cutest house you ever saw—not to mention adding a sweet granddaughter. It’s fair to say I am happy at this point—and very much over the trauma.

Gaby, who has become as much my friend as my therapist, has nevertheless bugged me all this time to open up to the idea of adding a man to this mix. So, about three years ago, I made a disastrous first foray by signing up to, the biggest site and the one I met Jim on nearly twenty years ago. I posted one picture and begrudgingly wrote up a profile. When I showed it to my sister Kathy, she told me my self-description “just screams ‘Don’t contact me!’,” then asked if she could share it with her friends because it was funny, though in an unmistakably acidic way. I left the profile as it was—which tells you how I really felt about the whole thing and probably explains a lot about how it all turned out.

I was 65 then and the inventory of men my age was pretty discouraging. I conducted a search using my three “must have” filters and found there was only one man in 200 miles who fit the bill. That guy did actually contact me on his own, but after chatting a bit, he asked for more pictures so he could make sure I wasn’t “a fatty.” I was actually downscale on my weight at the time, but the very question pissed me off so much I ended the contact. Honestly, a man who does not know that he shouldn’t ask or even hint about a woman's weight has no social awareness whatsoever. I’m not saying it’s unreasonable to wonder about such things, but if a man doesn’t know not to ask, he is going to be rude to waiters and God knows what else.

An illusion of youth. An assertion of virility. A display of wealth. Or an unwitting admission of impending mortality. Doesn't matter: if a man over 70 shows himself with a sports car, swipe left.

After that encounter, however, I took pains to populate my profile further, in part so no one could contact me without having a realistic idea of what I was like, but also because I realized that I had a hard time assessing men without a few pictures and some details. To get ideas about what would be good to include, I searched the platform without any filters to see what others were posting. That is when it got really scary.

Men my age apparently think it is attractive to post a picture of themselves on a motorcycle. As stomach-turning as a shot of a 70-year-old lying back seductively on his Harley sounds, there are enough of these to constitute a significant subsegment of the total online old men universe. The second largest class of photos is aging dudes posing by their cars, always either a luxury machine or something that passes for a sports car. If not a car, a boat.

If I may add a spin from my research, I can tell you that high base-level testosterone carriers are more likely than the average male to buy these things and they do it precisely because they think it expresses power and manliness. High base-level testosterone types are also more likely to be assholes (as measured by a range of indicators), so the information in these images is useful, if you know how to read it. Motorcycles, boats, sports cars = swipe left.

An inordinate number of over-50 men take their selfies with the phone held upward on a plane perpendicular to their Adam’s apple. Maybe they are too old to know Selfie Rule #1: Never take your own picture from below your chin. Still, surely they can look at the picture and see how distorted it is. But, no, they post it anyway.

An astounding number take their selfie in the bathroom mirror. The fluorescent lighting makes them look awful, but the worst is that the shower curtain or the toilet is visible behind them. You would think these dudes would at least shave before they shoot, but most of them haven’t. They are also usually wearing a tank T-shirt or they appear to be naked.

Some men post horizontal photos vertically or vice versa and some post theirs upside down. Quite a few post none at all. These guys usually haven’t filled out their profile, not even the adjective checklists. They seem to think that just being a man should be enough for any woman to want them. Swipe, swipe, swipe.

Women don't show themselves in the bathroom mirror like this. They have their own embarrassing genres.

What were the older women on this site like? Most were demure, motherly women; often they did have a little weight on them, as one might reasonably expect at a certain age and after children. But there were also cringe-worthy pix of 50+ women in those tie-front shirts, the buttons undone so you could see what was left of their cleavage.

The worst part of online dating is that, eventually, you have to meet up in person. Three years ago, I was still just too raw to do it. I had coffee with exactly one man before I ran for cover. We had a nice conversation, but the experience was extremely stressful and I was totally yucked out over the prospect of taking up with him or, really, anyone. So, after a few months of half-heartedly playing around on the site, I cancelled my subscription.

Fast forward to the present. Even with Trump gone, I am glued to the news every night, so I saw a whole bunch of new commercials for sites catering to those “over 50.” I pondered the prospect and decided that this may be a good time to try again. I am stronger now and the pandemic actually makes it easier. I have no intention of leaving the house until I get vaccinated, which means I wouldn’t have to meet anybody in real life for at least six weeks or so. I figure what people are doing—especially those of us in the “high risk category”—is zooming. Zoom seems a good interim step between chatting and the dread Coffee Date. You can cut your losses without leaving your desk.

These days, an essential message to communicate without saying it directly: your politics. This photo told any American viewer I'm a liberal because Democrats voted by mail. You can also just say you don't tolerate bigotry; it amounts to the same message. I did take this photo from below, though, and the effect is not salutary.

I decided to look at the most heavily advertised dating site for the elderly. Not too bad! I thought “what the hell,” signed up, and began populating my profile. I used all the lessons learned from the experience. I filled out all the lists and carefully composed my self-descriptions.

Photos that are five-ish years old misrepresent your current condition, so if you use them at all, I think they should be dated. I chose current pictures and put dates on all of them. Even so, when you are old enough that your skin is sliding off your skull, I think it’s hard for people to “read” your character from a current photograph. I had noticed that some men put up a photo that is clearly more than 20-30 years old, along with more current ones. I like that because I really think I can tell more about what an older man is like, as a person, by seeing a photo from when he was really young (along with current ones, of course).

And, honestly, I kind of think it is nice to see what a person puts forward as his best moment out of a long life. So, I put up my high school graduation photo, which I admit is probably the most flattering I have ever had taken. I also put a piece of artwork I have done recently, a pastel portrait of a woman from my African fieldwork. Also a funny picture of myself wearing a T-shirt Liza made me: it is screened with red glasses and reads “absolute badass.” All in all, I think what I have up there is honest, if a little flattering, and accurately expresses my personality.

Were his jeans up or down when he was chasing his "lady" around the barn? Was she wearing Daisy Dukes or brandishing a crowbar? Your mind can generate the scenarios indefinitely when what you really want is to stop thinking about it.

This site for the moribund automatically matches you with a list of people every day. I have been running through the matches rather carelessly each morning while doing my email. Very discouraging. Lots of motorcycles and bathroom mirrors, crosswise photos and bulging chins. Men so old I wonder if they have natural teeth left. (Men worry about fat. I worry about being kissed by accordion-pleated lips and toothless gums.)

A dispiritingly large number of these old boys write they are looking for someone to walk with on the beach at sunset. They probably also like Piña Coladas and getting caught in the rain. One guy with the most preposterous red mullet said he likes “chasing his lady love around the barn.” (I don’t want to speculate on what the pretext of that is supposed to be.) Obviously, this is stuff men think women want to hear. They all say they like to cuddle. I’m glad I am experienced enough to know there are no men who like to cuddle.

Scene 1. Old man does extreme sports to ward off fat women. Scene 2. His doctor has a heart attack just hearing about it.

To me, one of the most irritating things about these online profiles is the way a good many men answer questions about their favorite activities or how they spend their day. Favorite activities are invariably more or less extreme sports that effectively exclude conversation. They’ll list them in a whole string, uncut by any other more relaxing or inclusive pastime: kayaking, cliff-hanging, recreational avalanche-seeking. No movies, no speakeasies, not even a nice dinner. “I start my day by running 10 miles before breakfast, then doing 1,000 pushups on one arm. After eating a bowlful of nuts and bolts, I swim across Long Island Sound, returning in time to have undressed kale for lunch.” That kind of stuff.

Most of the time, these conversational gambits are merely further intimations of virility, I think. But sometimes they are meant to ward off fatties by implying a description of what you should be like—and what you must like to do if you are with him. This puts me off in itself because I remember too well that the men of my own generation often expect women to have no life, hobbies, or even preferences of their own.

In fact, my somatic interface fears that what these guys are all really looking for is a housekeeper. Because their wife has died and the house is getting dirty and they are tired of ordering from Grubhub. Ha! What righteous irony it would be for them to discover I have to straighten my house before the maid service comes so that they can see the surfaces to clean. I have already told you about my cooking skills. Grubhub is always a good option, as far as I am concerned, because it’s a step up from Lean Cuisine.

The worst ones will imbed a phrase like “I take care of myself and want a partner who does the same.” More magic incantations to expel the fearsome fatties. Don't even think about it: like I said, that guy will probably behave badly in public.

The hard truth: if these guys are in their 70s, they aren’t really doing any of this stuff because it would be against their doctor’s advice.

He was a very nice-looking man. But he seemed to love himself more than he could love anyone else.

One man contacted me from an upscale island off the coast of New Hampshire. He was dressed in a shirt and jacket and very nice-looking, if a bit corporate. He was even my age. An entrepreneur. But in answer to a profile question about what was most important to him, he answered: “1. My life. 2. Who I am.” I did too many years in a business school to spend one more minute with an ego like that.

Within only about two weeks, however, I had already had one emotional downturn. A guy wrote me whose looks appealed and who had a scientific research background. We chatted and really hit it off. He said nice things about my looks, which at my age goes a long way. I felt my spirits lift to a degree that I really did not expect. (I had maintained the stance, even in my own heart, that I really don’t give a shit about this.) We made plans to move to email and exchanged enough information to find each other online. Then he didn’t write back.

Of course, I thought my real online persona had turned him off. When you search, “Professor Linda Scott” or “Dr. Linda Scott,” my inaugural address at Oxford still comes up near the top. It’s a good speech, but it doesn’t exactly inspire desire. A Reuters journalist who saw another talk called me “formidable.” Great for my career, but “formidable” doesn’t get you dates. And, of course, the images that come up are all over the place. So, after I had carefully curated a becoming (but honest) photo album to show, my potential suitor was looking at my least-liked images, too. (I have got to change the one on the Said School site. Even at the time it was taken, I thought it was too corporate. Now it looks like another person entirely and creates a wholly false impression of what I am like.)

You can make fun, but, after all, they can reject you, too. The march-to-death app shows me who has looked at me and passed. In my current confidence-challenged state, I don't need the downer, but otherwise I think it is probably a healthy reminder that there is something off-putting about all of us.

In spite of my strong resolution to remain aloof, I was crushed when this man stopped writing. My kids are worried that isolation is making me too lonely, so Liza drove down from Boston to make sure I was ok. We sat in front of the fireplace while she poured us each a glass of wine (or three). She is an advanced online dater, as are most younger people now. She explained that I needed to change my game, to be less passive and more proactive, as well minimize my emotional vulnerability. “The strategy should be to increase your number of ‘at bats,’ like men do,” she recommended, referring to a hilarious Iliza Schlesinger bit we had watched together.

My COVID zoom look. Messy bun, chunky glasses hide that I have no make up. Pajama pants and slippers from the waist down.

Liza also pointed out that, despite the unfavorable denouement, this man had given me some esteem-restoring feedback—and so had some of the yahoos who whiz through my email. “you look very ptrettyand classy,” wrote one, “I need a lotof polish as I am a jeans and tee shirt person from when I worked around the houses but i clean up.” “You were the prettiest girl in the class!,” said another.

Liza insists, “it doesn’t matter who says it, Mom, you take it in and then go (straightens up and preens) ‘I’m hot.’” Thinking of myself as “hot” commits the same sin as the antique biker dudes, but it was a funny moment. It’s also good advice. We all need love but also to feel lovable. After the heartbreak of five years ago, I do appreciate the virtual winks, even if they come from a guy in an upside-down photograph.

Next day, I took her advice. I looked through my matches and wrote several of them instead of waiting to see who contacted me. I did this for several more days, enough to forget how many were “out there” and worry why they hadn’t written back. One of them did respond, a nice man from Connecticut who checks his investments before breakfast instead of kayaking, and we have been chatting for about a week. It’s mildly alarming that he wants to talk about monoliths and aliens, but I am reserving judgment.

We all want love. We all deserve to have it. Happy Valentine's Day!

With this strategy, I am not so invested, so it’s safer. And on Valentine’s Day, I admit that it feels nice not to be a sidelined grandmother, but instead to be out in the world looking for love, a sign you are still alive if there ever was one.

Wherever and whoever you are on this holiday for love, I hope you are feeling appreciation from a special someone, whether that’s a lover or your family or your dog or some dude in a bathroom mirror who writes to say that you are beautiful. Happy Valentine’s Day.

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