Thoughts About Dating Sites from a Woman of a Certain Age

Photo by Alex Holyoake on Unsplash

After a long, long, I mean really long deliberate hiatus of being more or less shut down to love and romance, I sort of woke up and decided I wanted again to find a mate. Even though, (or perhaps because) I’m definitely a senior citizen.

In my mind I had a vague notion of a lovely man about my age, give or take a few years. We would be devoted to each other till the end of our days.

I looked around and realized I was unlikely to meet such a man, or anyone even close, if I stuck to my regular routines. Since I earn my living online the idea of finding a beloved there appealed to me. I quickly bought a membership in After all, I figured, I had been one of their first 20 or 30 employees back in the days; I may even have written the first advice column on how to date safely online that a dating site ever produced!

No clue

Even with that background I only thought I’d know what to do. It turns out I had absolutely no idea.

First of all, I soon discovered that Match had lots of competition — although most of it seems to be owned by the same company. (Why did I sell my stock?) So I joined several — OkCupid and Plenty of Fish (POF) is where I landed plus one rather obscure board for people who love sailing called Because I do. Finally, because I’m now Buddhist I also check in with Dharma Match.

Initial search criteria

Once I registered and confirmed my email address, I set up my profile and uploaded some current pictures. Although writing about me isn’t my favorite thing, I muddled through. Some sites offer extended lists of questions to answer, others settle for the basics like gender and distance.

Each site also allows me to choose a search criteria so I can see who is (maybe, it turns out) available I began to do some searching.

I soon noticed I needed to create a personal list of warning signs. In my case I decided I wouldn’t pick someone who was only ‘recently separated’ rather than divorced. If his first two or three pictures featured him with a cocktail or a can of beer I moved on. Shots that centered on guns (rare), golf courses (lots and lots), muscle cars, or mall likely to be yappy (surprising to me how many) dogs caused me to pass.

I began to make some connections and have a few online conversations. These usually led to more eliminations. Twice someone suggested that although they had recently committed to someone, a friend just happened to see my picture while looking over his shoulder — would I be interested in contacting him? No. I can’t prove it but it smacked of the beginning of a scam since all these sites allow limited memberships at no cost.

More than a few allowed as they had either recently committed, or had just started dating someone seriously. It turned out that while I was often discouraged, I really appreciated these guys. Not all are so forthcoming.

Occasionally I’d meet someone for coffee once or twice but nothing clicked — I think I’m talking about sexual chemistry — or some sort of chemistry. Do we have any empirical understanding of chemistry between people? I certainly don’t.

There were surprises. For example, it never occurred to me that some men (I suppose some women do the same) would leave their profiles up for years. Apparently the dating service companies are more than willing to leave these probably outdated self-descriptions up forever, maybe because it fills the ranks. I never found a date or any other indication on Match or any of the other sites I’ve played with, to indicate when a profile was first entered. Sometimes with a close reading I’d discover that someone who seemed attractive to me hadn’t updated his information since his infant son had gone to high school. In one case I ran into a man seeking a woman and I knew the guy had been dead for several years! So I learned to play detective.

I found I also needed to ferret out dates on photos if at all possible. I don’t know why someone who is 80 and when you meet him looks at least that old thinks they can get away with pictures from when they were 60 or younger, but they do.

And if anyone can explain to me why so many men want to date women who are at least two years younger I’d like to hear it. It’s not always that way, but often enough to notice. Is that an American thing?

On the other hand, if in the picture there is any hint of a boat, I look further. I’ve lived on boats, done commercial fishing and even sailed in the south Pacific on nothing larger than a 32 ft. sloop (including a shipwreck which is another story).

I’m also a cat lover, so guys with cats are attractive. So are the men with big dogs because I grew up with big dogs. Sometimes I’d come back to a guy I’d passed before. Obviously I respond to more than the obvious information and pictures, but I’m never sure exactly what, so I label that intuition.

Not cheap!

Of course, the matchmaking companies are aiming for profits. While some will allow limited contact for free, others insist on monthly membership fees paid annually for the privilege. It’s not unusual not to be able to read a message from someone who likes you unless you join — and although you may have registered for free, actually joining requires money. Sometimes lots of money.

I’m loath to pay $15 or $20 bucks just to read what some guy I don’t know at all has messaged me. Of course if that month several guys send messages it starts to look more reasonable, but I’m as a senior I’m in a group that has relatively low population. I paid for several months at and ended up dating no one from there. OkayCupid landed me several interesting meetings at no cost at all. Go figure.

My bottom line

The most important truth for me right now is I’ve met several people I truly enjoy and had zero chance of meeting them any other way.

I wish the matchmaking companies would give us some clue about how recent or ancient profiles are — some do let you sort for ‘recently online’ or even ‘online now’ which is better than nothing.

It’s been fun, interesting, discouraging, etc., kinda like life itself.

Would I recommend online dating to a friend? Yeah, with caveats: start with lowered expectations, don’t believe a lot of what you read and always always meet in a very public place — exactly what I suggested oh so many years ago.

Writer, life and writing coach, book ghostwriter, Grandmother, Buddhist. Liberal who listens to the other side, political

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