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

July 2021

Abandoning Dating at Middle Age in Favor of Friendship: Time for going Lysistrata on this


Man and woman holding hands on bicycle
Photo from Unsplash

I’ve been reading lately about the difficulties women over thirty-five face in finding a good man. Statistically for those of us dating at middle age, it’s even worse when we’re over fifty. My conclusion: Dating itself has failed us.

Originally, dating led to marriage. Sex was coupled with commitment, and accountability was paramount. If a guy promised to propose but failed to follow through, you could sue him for breach of promise. Or your male relatives could just come after him with pitchforks.

Relationships today are amorphous, like a jello mold filled with yummy little marshmallows, but also full of those icky jalapeño flavored jelly beans. It’s not that we see our prospects as more than friends, it’s that we see them as so much less. Especially for the jaded denizens of dsting at middle age.

I call it the “what can they get away with” paradox, especially when dating at middle age. With sex uncoupled from commitment, I’ve met far too many guys who offer nothing but pricks. Modernity has become an excuse for societally sanctioned laziness, and worse yet, callousness.

Online dating has become a stage upon which we act our worst, then scurry away, as if the other person simply disappears because we want them to.

So while dating is off auto-erotically asphyxiating itself, let’s turn to friendship instead.

We need to stop seeing people as commodities and try to get to know each other as friends. But for this to work, we have to start seeing our prospects as individuals, each with a soul and dreams and foibles and feelings that can be hurt. They might even have something interesting to say if we take the time to get to know them.

We are far less likely to screw over people we see as friends than as fungible sexbots. And once we make a friend, we become more accepting of them. Acceptance may not lead to love, but it may lead to re-evaluating our required height-to-weight ratios, acceptable post-graduate institutions, and permissible footwear.

The majority of people on dating sites allegedly go for those few who are stunning and overtly successful— the alleged “quality” prospects. But I see plenty of long-term relationships develop between unremarkable-looking, middle-aged folk. The difference is that they know that quality isn’t determined by taut physiques or flashy jobs.

They know the truth: quality is measured by how we treat other people.

Instead of settling for less, let’s demand more, just on the inside instead of the exterior.

Can we talk about hiking?

Me at the top of Mount Diablo. No, I would not do an arduous hike with most of the men I’ve dated.

(I’m going somewhere with this …) On a recent group hike, a woman fell on a steep downhill, hurting her back. The next week, a female hiker couldn’t make it over the hills. In both instances, men they’d never met before stayed with them, helping the injured one to limp back to her car, waiting with the tired on while she slowly scaled each hill. These fellows sacrificed their own hikes, and their daily schedules, for women they didn’t even know.

I’ve rarely encountered that type of sacrifice while dating. In fact, I learned the value of my personal safety from an affluent guy I met for a date which lasted far longer than planned. When I said I had to leave to catch my train back to my car, he promised he’d help me get home safely. But when the date ended hours later, it turned out he planned on dropping me off at the deserted train station nearest his house.

Without complaint, I called an Uber. He then had the nerve to ask whether it was worth the price. Yes, I answered, to me my safety was well worth forty dollars. After a few minutes, he gave me a twenty as if he expected a medal. Twenty dollars was nothing to him, but once I was out of sight, and apparently out of mind, I became an inconvenience.

One more hiking example and I’m done. On last week’s group hike, a man came up beside me. He was friendly, if perhaps a bit oblivious, chattering on about his recent hikes, not noticing that I’d been conversing with someone else. As we made our way down a steep downhill, he stopped to offer his arm to a woman stuck on a rocky patch, helping her to cross over to safety. In that instant, I saw that he was a quality person. I’d been too afraid for my own footing to help that woman.

On a dating app, that Don Draper look-alike attorney alike standing next to his classic ‘Vette might look like a premium catch, but in reality, he might be a lot like the real Don, prostitutes and all. In contrast, the guy with the dreary, corporate head shot and tersely written profile might turn out to have hidden depths. He just isn’t a great self-marketer.

In fact, some of the better guys I’ve met online have shorter profiles because after a couple messages they want to talk and meet in real life. Be wary of the ones who waste your time frequently texting clever messages, sharing their days, or asking you a lot about yourself. They often disappear, negating your investment in all that texting.

But you wouldn’t do that with a friend. Nor would you try to talk a friend into bed over their reservations. Nor use them for your own entertainment then vanish, because you know, there might be hotter friends out there.

Quality becomes grossly distorted when it’s limited to a screen.

I’ve been reading how men are programmed to provide, and are thus confused by women who apparently do not need providing for.

This was not my experience in dating at middle-age. I could barely get a guy to meet for coffee at a specific time, not to mention getting him to lay a dead wooly mammoth at my feet.

Rather, men were far more likely to complain that I was the one who’d failed to provide. I went on far too many initial meet ups only to be treated to screeds about the cost of dating. And oh yeah, did I want a second nonfat chai latte? (Ringing in at $5.95).

Later dates offered other problems. There were the ones who disdained my suburban town and demanded I come to them, which I did a few times before tiring of making an hour and a half round trip with no reciprocity. Or the guy who picked a very expensive restaurant, proceeded to order enough imported Jamon Serrano and premium Rioja for four, ate and drank most of it, and only afterwards said, “Are we splitting this?”

The message I kept getting wasn’t “let me provide for you.”

It was more like, “Let me see what I can get out of you.”

And I am not alone. Friends with benefits, sure…but we need to be treated as friends, not just orifices that provide benefits.

We dissatisfied women may have to go Lysistrata on this.

Lysistrata is the story of a woman who persuaded the women who lived in two warring Greek city states to withhold sex in order to force their men to negotiate peace. We women who want long-term realtionships may have to start weeding out the chafe by waiting for sex until we have established a real friendship with our prospects.

I’d like to think that even the most casual of sex can include kindness, and even a measure of chivalry. But my own experience turned me into a nineteen fifties style prude. When I started at dating at fifty, I didn’t worry about buying the cow when the milk is free….until several guys started to treat me like interchangeable livestock after I gave up the cookie.

After a year of dating, I gave up on anything casual, because it seeemed to come with a measure of contempt. I decided to wait until I could answer the questions, do I actually like this man, is he a good person, and will he hang in there long enough to nurture a friendship?

In short, do I trust him?

He can tell you he’s as thrilled about you as a raccoon with a crayfish, but will he care that you get home safely and will he contact you again. He probably would with a real friend. And isn’t friendship the best foundation for leading into anything more?

See you on the trails.

(Previously published in P.S. I Love You).

Abandoning Dating at Middle Age in Favor of Friendship: Time for going Lysistrata on this2021-07-02T12:05:28+00:00

April 2021

Why is Dating in Middle Age so Hostile? It All Started on the Playground


Why is Dating in Middle-Age so Hostile? It All Started on the Playground by @DWeissWriter #dating #middleage

To me, so much of the dysfunction surrounding dating in middle age 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 featured incredibly good-looking lawyers with hot sports cars having way more sex than actually practicing law. It all embodied a conquest mentality: of saying what you think the other person wants to hear in order to get what you want. But that didn’t seem to apply to me as a female attorney.

My law school class was fifty-one percent women. But once I was practicing law at a firm in the real world, the male attorneys talked over me. No one asked my opinion. In fact, when I tried to speak up, my male boss told me that I needed to be more pleasant even though he himself was a Human Resources nightmare.

Pleasant is not a word used to describe a successful attorney.

Then there’s the second problem: not only were many of us women raised not to offend anyone, the media told us we needed to be considered beautiful, and therefore wantable. And if beauty is something we’re taught to aspire to, then being praised for it becomes validating.

Our social conditioning created the perfect shitstorm in middle age.

Combine the need to be desired with being trained not to offend anyone, and it’s back to the playground where we were told to play nice with the boys even as they pulled up those stupid dresses we had to wear. In other words, we’re raised to be susceptible to compliments about our desirability, and also to be afraid to tell our complimenters to fuck off for fear of offending them.

This all came to mind the other day when a girlfriend called me in tears because her dream guy who allegedly wanted to build a life together was pulling away following an intense three-month relationship. He told her he could still see them together, but he needed to see her far less frequently and only when he was up to it depending on his fragile emotional state.

“I don’t understand,” she whimpered between sniffles, “He told me I was stunning. He said I was the first person in a long time he felt serious about.”

But his behavior said otherwise. Leading me to believe that all his earlier verbiage was just persuasion to be with her initially. There was never any potential for a shared future. And if he did have emotional issues which precluded a relationship, he should have told her that from the start. As in before the pulling back of sheets.

That’s the problem. Words are just words. We believe them because we want to.

The problem arises when we try to get the other person to bend to our will.

A millennial friend recently taught me a new word: Fuckboy. It refers to a guy who is unsure of what he really wants from a romantic partner. But he acts like he is more involved or enamored than he actually is in order to scratch the romantic/sex itch. He is “superficially intimate, as if acting from a script he knows all too well.”

I’d call him a Lothario, and I’m disheartened to find out he’s still flourishing in the modern age.

Assume my prospect says, “I’m looking for a woman to have sex with when I don’t have anything better to do.” At least I know he’s not for me, and props to him for being honest (if somewhat lackluster).

But what if he says, “You are so amazing, a combination of strawberries and wood musk. I’m already crazy about you. Let’s try to make this work.” Unless he’s ushering me into the backseat of a Camaro, I might be apt to believe him.

In effect, both statements could mean the same thing.

When I started dating in middle age at 50 after losing my husband, I was surprised to meet some men who wanted me so much, I was just so irresistibly desirable. Which of course I wasn’t. I was just woefully inexperienced (having married my high school sweetheart), and happened to be there at the right time with a middle-aged guy who had a silver tongue.

But it left a bad taste in my mouth.

There is a one-word solution to this dating in middle age problem, It’s called compassion.

We need to treat our prospects as people we care about instead of transactions we hope to benefit from. Most of us put kindness aside in the dating world. If we’ve met online, we have no history with these people. We never have to see them again, and it’s easy to talk ourselves out of being accountable to them.

All the people who’ve disappointed us in the past blur into this mess called “dating,” so we treat our prospects like we already know it isn’t going to work. Why waste time being courteous or even showing up if we find something better to do? That sock drawer is looking pretty darn messy.

Or we fear getting taken advantage of if we treat someone kindly. Like listening and offering empathy instead of vacuous compliments will lead to demands for expensive dinners and low-interest loans.

But if we think of our dates as potential friends, compassion comes to the forefront. No more trying to lure them into coming over with false promises of fake futures. No more hackneyed compliments in an effort to make a conquest. And even more importantly, no more degrading ourselves by treating people as if they’re disposable.

I know I’ve felt sullied by the morass that is online dating. But that happened when I’d given up on people and, to my discredit, stopped behaving accountably. Cynicism led to irresponsibility, causing me to feel even worse about myself. Treating everyone kindly might not lead to romance, but it definitely helps with self-respect.

And when we like ourselves, we behave better to others because we have our own self-worth to answer to. Let’s stop trying to come out ahead, and see the person in front of us not as a conquest or a fuckboy, but as a real person who might become our friend.

If we’re lucky, it might start a chain reaction.

(Previously published in P.S. I Love You).


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Why is Dating in Middle Age so Hostile? It All Started on the Playground2021-04-09T19:35:12+00:00
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