Cyber-Dating in One’s “Golden Years”-or Not Old Enough to Know Better

Are you ready for this? Relationships end. When that happens, people are thrown into the snake pit that is the world of modern dating. And if you’re a senior…

One thing we older daters learn quickly is that the meet-and-mate scene is biased toward those under forty. The night, especially here in Manhattan, belongs to the young. (How many clubs can you think of where Mel Torme whispers in the background and people can hear each other speak?) People in their middle ages and beyond, especially urban-dwelling seniors, have to turn to our computers to find the smiling face that may one day greet us across the breakfast table. And that means cyber-dating sites.

You’ve heard their names – CraigsList, Zoosk,, Plenty of Fish, OKCupid, eHarmony, Then there are the religiously focused sites – BigChurch, JDate, Christian Mingles, CatholicMatch. The list is growing every day. More recently, webmasters are beginning to target older singles – OurTime, HowAboutWe, DatingForSingles, SeniorMatch,, SeniorFriendFinder. The list grows. A few of the above are free sites, notably CraigsList, Plenty of Fish and OKCupid, but most of the others draw you in with free searches and then charge you to make contact with the desired person or persons on whom you set your sights.

After a long relationship ended, and as soon as I was ready to start dating again, I invested in, a pay site. I paid for about six months, but found most of the women with whom I chatted to be guarded and rarely willing to meet. They seemed over-cautious, exactly the opposite to my newfound recklessness. At the same time, I cruised the personals in CraigsList.

Within the first month of my dating adventures in Craigslist I met Reverend C. She was a renegade Westchester housewife who’d gotten her doctorate of divinity, bugged out from home and moved helter-skelter to the Upper West Side where she was plying a faltering trade as a Jack-of-All-Trades. The Rev. was a hot number. I erroneously believed that this was what awaited me as a new bachelor.

Consequently, I figured I would be in big demand, among my age group, that is. So when she started complaining about her financial state and made it pretty clear that she needed a sugar daddy, I drew back. There were plenty of fish out there. (In fact, there was also that website.) She kept trying and I kept resisting the temptation to finance her, so she ended it and got married two months later. I returned to the senior dating sideshow.

There followed a series of hit-and-miss dating adventures, and I was often made painfully aware of the chief drawback to senior dating: caution. People this far advanced in years have too much experience to be laid back in relationships; they carry baggage and that baggage will be acknowledged!

Julie T. was an – get this – assistant prison warden who said she was a body-builder as a way of not being honest about that body. What was honest was that she should have stopped the building part years earlier. Of course, these were women I gave up on. I won’t go into all the times I didn’t make the grade as a suitable suitor.

Once upon these times, surfing Craigslistings with images, I came across diminutive Carrie’s photo. She looked good – age-appropriate and all – so I contacted her. More than once. When she replied ten days later she apologized for her reticence. It wasn’t that she was uninterested, she just found it necessary to stay by her cousin’s side while the ailing relative died. “I sort of have to help my cousin die.” She said she hoped I’d understand, and that she’d be unavailable for a spell. I replied that of course she had to perform this humane and extremely kind service, and that of course I’d be willing to wait. A month later we agreed to meet. I didn’t ask her about her cousin, assuming that the matter had been, er, laid to rest.

We soon were in a small bar sharing a wine at sunset on the Hudson. The early part of her conversation was I believe structured to convince me that she wasn’t older than she claimed. She said that the scar that ran under her neck, from ear to ear, was not from plastic surgery, but from a “fall.” I tried in vain to imagine a fall that would come close to ripping one’s face off, but I decided not to pursue that train of thought.

She was talking about her family. When I came out of the reverie that her scar induced, she was talking about the dysfunction in her family. Now, that was something I could relate to.

“I have something to confess,” she said. “My mother committed suicide.”

Hmm. “Well, it happens in the best of families,” I replied, then quickly changed the subject. I asked her about her work.

Maybe because I zoned out when she described her job, or maybe because she was just on a jag, she went back to her mom’s suicide.

“…and it took me two weeks to convince the police that I had nothing to do with it.”

“Well, you know how it is – CYA. They’ve gotta cover all the bases, you know.”

She didn’t know CYA, and kept on talking – me half-listening, watching the sun setting bright red over Jersey.

“…and before she died, my mother confessed to me that she murdered my sister.”

Oo-kay…time to return to planet Earth! “Come again?”

“My sister,” she explained, “had become a hopeless drug addict for twenty years. So when she was forty-one – overdosing and bringing junkies home with her – my mom fixed her a drug cocktail.”

“She killed her?”

“She told me she was better off that way.”

“My god!” But that wasn’t all…

“Then she told me she also killed my father.”


“It was a shame. He had been such a vital man, always turned on by life, full of interests. Then, around his seventy-fifth birthday, it all started to fall apart. By eighty he was turning into a vegetable. So my mom told me she poisoned him because he ‘would have wanted it that way’.”

Her voice trailed off as some of her earlier words echoed, booming in my icebox skull….

“…and it took me two weeks to convince the police that I had nothing to do with it.” and “I have to help my cousin die.”

We sat before our identical glasses of merlot. I had never looked away from those sunset-glittering wine glasses, not even for a moment. Or had I? Should I distract her and switch glasses–just in case?

I walked her home a half hour later, a peck on the cheek. Ironically, two days later I got an email from her saying sorry, there just wasn’t any chemistry. Damn right! I thought, with some relief.

For a week or so I struggled with the idea of contacting the so-called authorities. But who would that be? Craig of Craig’s List? The Loony-Old-Man Squad? Commissioner Kelly?

Judge Judy? Then I told myself to forget it. I recalled other things she told me, things about her job. Specifically, how she would soon be working personally with Rupert Murdoch. And I thought, Tea, Mr. Murdoch? and went back to surfing those sweet smiling faces.

*Dr. Bashkatz is not licensed to practice anything anywhere.

1 thought on “Cyber-Dating in One’s “Golden Years”-or Not Old Enough to Know Better

Leave a Reply