The Precarious World of Online Dating After 50

“You’re cute, do you have a younger sister?”

“Hi there, what is your sexual appetite?”

“Can I fist you? Women in their 20s and 30s don’t like to be fisted?”

“How bout a full-body massage in exchange for a shoulder rub?

“No way you’re THAT old”

“I have mommy syndrome and would be heaven going down on you”

That’s just a random, word-for-word sampling of the text messages I get from my online suitors. No kidding — these are their opening salvos. You’d think men would have matured by this time. In fact, the opposite is true.

To be honest, I never would have imagined that I’d be single post-50, without kids and attempting to date in New York City. But, alas, this is my predicament.

Independent, financially secure and very, very single.

And it’s challenging. I often equate quality single men over the age of 45 to the endangered species list updated nationally by the government. Where are they hiding? Certainly not on the dating apps/sites I have tried over the last two-plus years.

OK Cupid, Bumble, Hinge, Happen, Tinder, Match, eHarmony…I’ve tried them all.

Back in 2003, I moved to New York City from Seattle, following a divorce after an 11-year marriage. The last time I had actually dated was 1989 — AKA, pre-internet, pre-social media, pre-cell phones. I had to learn to date (and have sex) all over again.

But online dating from 2003 to 2006 was quite different than it is today. People actually took the time to create profiles and would even READ your profile before trying to contact you. No longer. Today, we live in the era of swiping. When asked what sites are best for women, I laugh — I see the same men on all of them with slightly different takes to their very short descriptions.

It was between 2003 and 2006 that I met the man I would be with for eight years in what I thought was a committed relationship. As things broke down, my fear of going back to the dating world struck a chord of horror in me and kept me stuck in a very toxic and negative situation. As bad as things were, returning to the world of digital dating was a decision I desperately wanted to avoid.

Nevertheless, I ultimately found myself back on the market. So here I am today: swiping, swiping, cringing, laughing and, yes, sometimes crying. And, yes, I force myself to keep it up, as painful as it can be. I also accept dates from men who may not seem ideal on paper because one never knows.

So far, other than a small number of positive connections that led to a few weeks of dates, I can honestly say I’ve been far from “enchanted” by online dating in recent years. To get by, I try to tell myself that one can always benefit from making new friends and acquaintances.

Most of the dates have been the epitome of dull. Recently, I was to meet a fellow at June Wine Bar in Cobble Hill. He was coming from Manhattan and did not know his way through the streets of Brooklyn. He expected the bar to be right across from the 2/3 train stop at Clark Street, and instead it was about a mile away. He never even checked the map! He called me completely lost. I took pity on him and wrapped up my tab at the bar to dash off and meet him closer to the stop.

When we finally sat down at another bar, within minutes he started to tell me about his ex-wife’s infidelity. THIS WAS THE FIRST DATE. His words slid into what sounded like the adults in Charlie Brown comics, and I started to daydream about going home and cuddling with Phoebe, my pup. After two glasses of rosé (while I mentally planned my week of client work), I politely said goodnight and exited the establishment.

Another date ended as quickly as it had started when my date broke it to me that he voted for the current white house occupant but was too “chicken” to tell me before-hand.

The good news is that I date on my terms: I select places close to home for an easy escape, I always ask a friend to call me so I can say “an emergency” has come up and I must depart and I definitely choose watering holes that I know will have a decent selections of wines-by-the-glass so I can have some fun. Lastly, during spring or summer, I pick outdoor spots so Phoebe can accompany me. She makes an excellent chaperone and has exceedingly good taste.

As an optimist at heart, I’m convinced that I must keep trying. When asked if I’m looking for the “one,” at this point, I honestly do not know. A friend with benefits who is intellectually curious with a love of travel and adventure has a very nice ring to it. I am, however, looking for that real connection, deep conversation and mind-blowing sexual intimacy.

And two-and-a-half years following my painful break-up, I’m still searching.


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