March 2023

Do People Over 50 Fall in Love?


Man and woman arguing

I had no idea dating over 50 would be such a power struggle. Here’s Why.

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 before the fire, goblets of red wine in hand. I looked forward to our first real kiss.

Instead, he launched into the story of an ex-live-in girlfriend he described as a super hot blonde with breast implants (not that I needed to know that) who wrecked his finances, was mean to his kids, and talked him into buying a house he couldn’t afford, before cheating on him with a guy from the gym.

“After her, I sort of lost hope,” he concluded hours later before going into a second monologue about several other women who’d destroyed him. His ending salvo, “As a widow, I know you’d understand pain.” I hadn’t realized that was my main selling point.

I figured Mark was an anomaly, a severely disillusioned man who used his dates as pro bono therapists. But I was wrong.

My next prospect was a wealthy artist with anger management problems who told me I reminded him of his emotionally withholding mother. He too claimed to have spent years searching for love without success, but he seemed to think that I was the embodiment of his past failures, or at least that I wanted to hear about them.

Worse, he was mean, complaining about all things large and small, and once again, expecting an emotional labor machine in a push-up bra. He even whined in bed that my legs were so long he didn’t know what to do with them.

After a few more failures, I went off J-Date and tried some other sites, OK Cupid,, Tinder, and the cesspool that is Plenty of Fish. But my dating life didn’t get any better.

Not only were many of these guys disillusioned, but they also put no effort into getting together. So I received last-minute offers to meet at some guy’s local watering hole that night or asked when I might be passing by their way, no coming to me, or some guy I’d just met was already sniffing around my bikini line even though my profile clearly stated I was looking for a long-term commitment. After an initial meet-up, I got offers to “c’mon over and hot tub” as a second date.

I was a lonely widow who was seeking a life partner, but many guys said what I was looking for didn’t exist anymore. I wanted a relationship that encompassed not only travel, sunsets, and other dating profile cliches, but also home repairs and doing dishes together, and being there when things fell apart. In short, I wanted a love that lasted.

Why It’s So Hard to Date at Mid-Life

Being an overly analytical, former lawyer, I came up with several reasons why so many middle-aged, heterosexual guys were so disillusioned with long-term relationships.

First, few people want to be dating at this stage in our lives. So many of us expected to be spending our later years snuggled comfortably together with our prior life partners.

My husband had the poor taste to die, but I’ve met many divorced guys who feel they did everything right before — providing financial support, putting family first, agreeing to their wives’ demands — and look how that worked out. So, they come to dating already angry about their pasts and disillusioned with love.

Moreover (and this is a gross simplification), I’ve read that men tend to externalize anger, looking for someone to blame for their situation, while women tend to internalize it, taking the blame for their situation upon themselves. So, we get a pool of people who never wanted to be there in the first place.

Add in that men of my generation were raised to conquer, think James Bond movies, Gordon Gekko with “Greed is Good,” and my own personal guide to yuppiedom, L.A. Law. But women my age were raised to not offend, to keep our skirts down on the playground as we were told to just ignore the boys who tried to lift them up.

As a young lawyer in the late eighties, I was told by my law firm that I needed to be more “pleasant,” a complaint I doubt my male co-workers received and certainly not a word used to describe a successful attorney.

Finally, I think a lot of guys use hook-up culture as an excuse for bad behavior. But there’s a huge difference between not being committed and treating your date badly.

You can still show up on time, open doors, and not whine about the extravagant cost of dating or the last person who allegedly ruined you. Meeting a new person should come with a sense of possibility, not impending failure.

There are Happily Ever Afters

After five years of dating, I did find my second forever person. We met online when he sent me a message asking if the shoes I was wearing in one of my profile photos were Vans with a skull print because he was interested in getting a pair for himself. I answered that indeed they were.

I knew he was the one when he invited me on a Memorial Day Drive down the Marin coastline with stops at his favorite restaurants. When I offered to meet him at his place since it was on the way and my place was a half hour in the wrong direction, he said he’d pick me up, it was what he did. I hadn’t encountered chivalry for a long time.

Even better, on our first romantic getaway, he patiently listened when I talked about competing bids to replace my broken air conditioner, suggesting I go with the family-owned business which called me back on a Sunday. We’ve been together for five years now.

Best of all, at 62, he believes the best is yet to come. And that sense of possibility is what keeps us moving forward, believing we can find joy at any age.

If you enjoyed this article, you might enjoy my book, Available As Is: A Midlife Widow’s Search for Love about dating post-widowhood. More information on my website here. and you can get it on Amazon (or your local bookstore).

This was originally published on Medium. 


Do People Over 50 Fall in Love?2023-03-26T14:11:08+00:00

February 2023

Benicia Magazine: Booktails.


Available As Is by Debbie Weiss

Article on

At first glance, I didn’t think a memoir from a midlife widow would be for me. I’m neither in my midlife nor a widow, so I worried I would have nothing to gain from the author’s writing. It wasn’t until I discovered that Debbie Weiss was a Benicia local and heard some feedback from the people in our town who’ve read the book that I decided I would give it a go. And I’m delighted that I did.

Available As Is: A Midlife Widow’s Search For Love by Debbie Weiss is a memoir that takes us through Weiss’s experience with processing her grief, entering the dating pool in her fifties, and learning how to find fulfillment outside of a romantic relationship.

Weiss and George began their romance at her high school prom and quickly became each other’s one and only.

However, when George dies of cancer, Weiss is left picking up the pieces and beginning a new chapter of her life at 50.

Starting with endless Manhattans and TV show binges, Weiss grapples with finding a way to navigate being alone for the first time in her adult life. We see her join one dating site, attempting to find a quality connection. Then, when that fails, joining multiple sites and averaging two dates a day at her local coffee shop, hoping that quantity will be the solution.

Weiss tells these stories with humor and absolute candor, allowing us to feel like a fly on the wall of every restaurant, bar, and ranch we are brought to. Weiss discovers that dating in her fifties is a messy affair and does little to distract her or help her heal from the grief and guilt of George’s passing.

As Weiss struggles to hold on during this challenging transition, she finds kinship in her fellow yogis and writers.

A regular yoga class turns into a group of intimate friends supporting each other through their individual challenges. A writing group helps Weiss gain confidence in her art and progress in her writing career while giving her a space to speak honestly and openly with people who want to see her succeed.

What I assumed would be a guide on dating for women in their fifties is actually a memoir that teaches a lesson we all need to learn, regardless of age or relationship status. Investing in yourself as an individual is the best way to grow and build the life you deserve. True friendship and valuable relationships will follow.

In this way, Available As Is is a stunning memoir for widows, divorcees, married folk, young and old, and humans of all genders. So pick up a copy from Bookshop Benicia and keep an eye out for any future book signings or readings from our talented local author.

Benicia Magazine: Booktails.2023-08-22T18:27:07+00:00

November 2021

Visit Me on Youtube with Celebrating Act2


I am so grateful and excited to be a regular contributor on Celebrating Act2, a video blog which offers advice on living the second half of your life. Every other Thursday, I’ll have a new post offering advice and dishing about the cesspool that is middle-aged dating.

Here’s my interview with Celebrating Act2 chatting about my upcoming posts:


And here’s my first ever post by myself discussing the biggest problem with dating at middle-age:


I promise I’ll improve! This is definitely a learning process. Please watch, share if it resonates with you, and let know what you think!

Thank you for choosing to spend your valuable time with me,



Visit Me on Youtube with Celebrating Act22021-11-17T20:31:48+00:00
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