To me, so much of the dysfunction surrounding middle-aged dating boils down to the way men and women of my generation were taught to behave.

Specifically, little boys were brought up to conquer while girls were brought up to be docile.

In the early seventies, when I started first grade, little girls weren't even allowed to wear pants to school. The boys were free to cavort on the monkey bars, but we girls had to play while holding down our dresses so they wouldn’t fall over our heads. That image pretty much says it all.

I started law school in the mid-eighties, the time of yuppies and Wall Street (“Greed is Good”), and LA Law, which…

When I started dating again after being widowed at fifty, I wondered, where are the men who act like grown ups? The ones who get their gutters cleaned, keep their homes reasonably tidy, have edible food in their refrigerators, and want a life partner instead of easy sex.

The ones who want a love that lasts. Even though they know it isn’t always easy.

I wanted someone who truly cared about me, who’d be there on the days that were hard for me, like my late husband’s birthday, and would listen to my worries over home repairs, and be available to talk even on the days we weren’t seeing each other. …

When I started dating at fifty after losing my husband, my biggest surprise was that everyone was disillusioned. Most of the men I met weren’t expecting much beyond an empathy machine. One long single guy opened our date with, “I realized I so excited to meet you because you haven’t been divorced so you’re not broken like the rest of us.”

Um, no, I was widowed and in my own kind of fresh hell. But I wasn’t yet disillusioned. I’d had a long marriage to a good man to whom I’d still be married if he hadn’t died. …

I’ve been hearing lately from several guys who are having trouble getting follow up dates. My best advice: To find love, develop your empathy muscle.

In my experience, many middle-aged men have let it atrophy.

Why dating is like a law firm.

Let’s go back to the early nineties when I was a young attorney at a mid-sized law firm. So often the conversation among the male lawyers constituted one-upmanship, be it exceeding billable hour requirements, having more accomplished children, or taking self-improvement vacations involving deep sea diving or extreme parachuting.

Some of the more experienced attorneys tried to get the younger associates to work for them…

Oh Peter, I feel for you. I have two friends who just can't get over their exes and be there with new people. Maybe it's a fear of rejection or the potential for hurt in a new relationship. Therapy has helped me with my memories. Good luck on getting vaccinated!

Thanks so much, Ahona. Sorry to hear the man child is a multi-generational thing. (And the comments...I know!)

When my husband died in April of 2013, I didn’t think I deserved to have a future.

By the time he was diagnosed with male breast cancer, it was already at Stage Four. At least, that’s what I believe. He never told me about having any symptoms until he announced one day that he was going to the hospital for “tests.” But by then, it was too late.

As he got sicker, he fell into deep denial.

He rejected care, wouldn’t let me get involved in his treatment, and demanded that we conceal his condition from his parents. Over time, I dressed the weeping wounds the cancer had carved…

Thank you John. Good point about being open-minded.