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. 


Order My Book Here

Follow me

Are You Ready to Date After Your Loss?

Subscribe here to get a Free Checklist to your inbox!

(noscript) -->