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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