Do People Over 50 Fall in Love?

I had no idea dating at midlife would be such a power struggle.

Debbie Weiss
Published in
6 min readMar 12, 2023

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Photo by Vera Arsic on Pexels

In 2013, I lost my husband to cancer after having spent 32 years together; he was my high school prom date, my one and only. Fourteen months later, still missing him beyond measure, I decided to try online dating even though I hadn’t dated since 1980 when I was a high school junior.

Back then, at least in my small Northern California town, if a boy wanted to ask you out, he called in advance, offered an activity he thought you’d both enjoy, and often showed up wearing a sweater his mom had picked out. He made sure you got home safely.

In 2014, when I started dating as a 50-year-old widow, I didn’t expect things to be that different. Having been with my husband for most of my life, I still believed in love and figured that other midlife people did too.

When Dating Becomes A Power Struggle

I started with J-Date, the self-proclaimed “largest Jewish dating network,” hoping to find my second bashert. My first dinner date post-widowhood was with Mark, an Alec Baldwin lookalike with a gym fixation. I’ve always had a crush on Alec Baldwin.

We went for a romantic dinner and walk through downtown San Francisco holding hands, returning to my place afterward to sit…

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Debbie Weiss
Debbie Weiss

Written by Debbie Weiss

Author of award-winning book “Available As Is: A Midlife Widow’s Search for Love.” Essays in Huff Po, the New York Times’ Modern Love and others.

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