Dating Leonard

The reality of dating a golden bachelor

Eileen Pollack
Human Parts
Published in
7 min readMar 8, 2024

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Photo by Natalia Sobolivska on Unsplash

This was 2019, a year before the pandemic turned us all into hermits. I’d retired to Manhattan, in part because I’d been divorced too long in my small Midwestern college town and the dating pool in New York would offer more opportunities than my former students and my friends’ ex-husbands.

“You’ll find a million men to date,” a New Yorker told me. But most would be artists or actors. “And every single one will be bat-shit crazy.”

This turned out to be an accurate prediction of my experience.

So, when Netflix suggested I watch a new reality series called Dating Around, I couldn’t help but tune in. The first three episodes chronicled five blind dates for each contestant — Luke, a straight white Southern guy; Gurki, a confident, divorced Indian American woman; and Lex, a cool Asian American gay guy — and I was startled to observe that none of the three picked the person I would have picked if I’d been them. Maybe that was why so many of the men I’d judged my perfect match never called for a second date. Or why I kept choosing men a disinterested observer would have judged wrong for me.

Then I heard the announcer introduce the fourth contestant — Leonard, a widower in his sixties who’d been married to an artist named Susan.

Leonard? My Leonard? Eight and a half million people lived in New York, but how many widowers named Leonard had been married to an artist named Susan?

Leonard and I had met three years earlier on Match. We’d rendezvoused in Riverside Park, and I’d immediately been smitten by his puckish smile, sexy shaved head, and wiry, muscled frame. If I squinted, I might even have fooled myself into believing I had a date with every Jewish woman’s heartthrob, that other Leonard, Leonard Cohen. I found this Leonard’s far-left politics to be refreshing. His history as a journalist, lawyer, and private investigator was a complement to my own bumpy past as a physicist, writer, and professor. The air between us felt electric with possibilities. We bumped hips. We kissed. We agreed to meet for a second date.

But over dinner at a Chinese restaurant, Leonard regretfully informed me that he didn’t “feel fireworks,” the…

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Eileen Pollack
Human Parts

Eileen is the author, most recently, of Maybe It's Me: On Being the Wrong Kind of Woman