Jdating in My 60s: ED Meds, Grandkids and Other Adventures

When my late husband Eliot was on his deathbed, he predicted which of our friends would ask me out at his funeral. He guessed it would be jazz-writer Neil. He was right. Though Neil insisted that going to a black-tie awards dinner didn’t count as a “date,” I had no interest in dating anyone for another seven years.

And then, at age 64, I did.

As a partner with “BigLaw,” I went about the process like any high-stakes project. I signed up with Match.com, eharmony, and Jdate. I posted photographs of myself sitting in a friend’s antique Bugatti thinking it would show a hint of class.

The Art of the Photo

However, the photo didn’t show a hint of body or legs, and therefore was ineffective as a self-marketing piece. I replaced those photos with shots of myself standing in front of this same friend’s yellow Ferret Scout Car, a small “British armored fighting vehicle…produced between 1952 and 1971,” per Wikipedia.  The bounce-lighting on my face washed out a few “etchings of experience.” That drew more interest from the fellows, and a few invitations to the Petersen Automotive Museum.

Picking a suitable screen name was a challenge. I thought “Turandotti” would display an irresistible mash-up of culture and whimsy. Indeed, it got me a few responses, all from rabid opera fans who assumed they had met the (albeit mature) princess to their Prince Calaf.

I changed my identifier to FlightRisk. This one proved paradoxically reassuring to the men whose profiles promised an interest in long-term relationship/marriage. FlightRisk described herself — well, myself — as a savage graffiti artist trapped in a lawyer’s body, launching her first date since her engagement to Eliot in 1979!

Proper Etiquette

That brings me to the etiquette of dating while senior. Do we pretend we have not seen the prescription ED medication in the master bathroom while snooping, or are we pleased that nothing will be left to chance, just in case…

Do we feign surprise when our date tells us that his now-teenaged children were carried by a surrogate? Or is it better — more flattering — to reveal a documented interest in the fellow, but in a blasé way, not in that OMG way. As in, “Oh, yes, I read that in an old issue of Us magazine I happened to notice online. Is that magazine still published? Shame about the dying print industry, don’t you think?”

Age? I assumed one fellow was five years older than me, as he’d represented despite his weathered appearance. He sailed, hiked, and did other sun-damaging outdoor things. A lifetime of that can wizen the dermis of the most conscientious applier of sunscreen. I saw no reason to doubt his claimed age.

Until a writer friend my age, Seth, took me aside to advise that when he was a child, he was allowed to stay up past his bedtime clad in footie pajamas to greet this same man, a good friend of his parents. Do I confront my date with “I only took two years off my age, Buster. There are rules for these things!”

No, I Don’t Want to See Your Grandson’s Photo

Some of them had grandchildren. Many seniors do. Nothing spoils a potentially romantic dinner like the prod of the iPhone: “Look, here’s a picture of my grandson Jonah with a strawberry ice cream cone!”

“Yes, beautiful child. Enchanting! You showed me that lovely picture last week.”

“Couldn’t have! Just took this one yesterday. You must be thinking of this one.” (Scrolls through a week’s worth of grandkid pictures for last week’s ice cream photo.) “See, that’s Jonah with his chocolate ice cream.

Then there were the widowers. A better potential fit? One such gentleman took me to a then-hot “little plates” restaurant, where a few tiny nibbles cost more than an entrée at The Palm. Our individual plates were not cleared between the first serving of some country pâté with a mustard-based sauce, and the second, a pure white fish mousse.

I asked the waiter to bring us a fresh pair of individual plates. The plates were produced. The next few tasting plates led to the same discordant situation. I summoned the waiter and said, “Look, I don’t want to ask you each time. Please bring us fresh individual plates when you bring out fresh servings so we are not slopping into flavor B with flavor A’s detritus.”

The waiter did so, a few times, but then forgot, and I summoned him for a follow-up request. I gave a rueful look at my date, and to my shock, his eyes misted over. “What’s the matter?” I asked in horror. Sympathetic horror, to be sure.

“My late wife always hollered at the waiters about the plates here — it would embarrass my daughter to no end — and you’re bringing back such wonderful memories,” he said. “I haven’t felt this cared-for since she passed.”

2 Coincidences; Real Love

Eventually, I met a handsome, amusing man on Jdate whose screen name was CitiBred.   He’d gone to Bronx Science High School with my late husband, and by uncanny coincidence had been to a SoCal reunion of Bronx Sci grads at our house in the Hollywood Hills. I invited him to my house for our first date — we had met before, though briefly, so how dangerous could he be? I served a little nosh and he exclaimed, “This is better than the jail food!”

“Right…thanks…the jail food…”

I meandered to the side door, calling out to this stranger in my most casual indoor voice, “Just off to the powder room! Back in a sec!” A long story, and far less dramatic than I’d feared: an employment rather than an incarceration thing.

We’re celebrating our 8th Valentine’s Day together looking for a street artist to paint a big wall in our loft. I only have the soul of a savage graffiti artist, not the chops to make the painting.

Jane’s AGEIST profile is here.

See medical disclaimer below. ↓


  1. Just got mail. YOU SAID THIS
    “Loved the story of your search for a soul mate as a widow lawyer over 60.”
    PLEASED TO MEET YOU! Please feel free to email me more: thoughts about lawyers and widows!
    I am glad search for a soul mate search sparked your comment.
    So here is my life story about being married over 27 years in life’s adventures in a dramatic comedy with 3 different women, three marriages three divorces 3 wives (1x(8) 2x(4) 3x(15) = 27 years respectfully I spent 27 YRS of my life
    married to the 3 different women
    3 different female personalities – extraverted personality styles
    all of them are wonderful beautiful women, to this day.
    I have lived alone since 2001 “dancing by myself ” = autonomous living the minimalists like of wealth and fame. where Legends Lounge


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The ideas expressed here are solely the opinions of the author and are not researched or verified by AGEIST LLC, or anyone associated with AGEIST LLC. This material should not be construed as medical advice or recommendation, it is for informational use only. We encourage all readers to discuss with your qualified practitioners the relevance of the application of any of these ideas to your life. The recommendations contained herein are not intended to diagnose, treat, cure or prevent any disease. You should always consult your physician or other qualified health provider before starting any new treatment or stopping any treatment that has been prescribed for you by your physician or other qualified health provider. Please call your doctor or 911 immediately if you think you may have a medical or psychiatric emergency.


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