April 2021

This Is How We Can Overcome the Bitterness Of Middle-Aged Dating


This Is How We Can Overcome the Bitterness Of Middle-Aged Dating by @DWeissWriter #middleaged #dating #bitterness

Looking cranky!

If I could describe middle-aged daters in one word, it would be bitter, and that bitterness is destroying our chances of finding love.

Let’s start with the origins of our bitterness

For many of us, our resentment began with the very event, usually death or divorce, that caused us to be single in the first place. We never expected to be in this situation at our age, and we’re still in mourning for our past lives, or at least our idealized versions of them.

As we set sail on the murky waters of adult dating, we feel that fate has already failed us. We’d assumed our lives were settled, only to discover our partners weren’t who we hoped they were. Or perhaps they’d had the poor taste to die prematurely. So even as we push off the dock, we are coming from a place of abandonment.

Our bitterness only deepens when we go online to find ourselves adrift in a haphazard culture of disposable people. We go from being “the one” to becoming one of innumerable seekers in an impersonal, sometimes hostile, environment. We’re subject to fake profiles, false representations, self-delusional photographs, and for women, allegedly playful sexual innuendos which come across as rape culture.

Sane people do not send unsolicited photographs of body parts

By the time we do meet a real, potentially sound individual, we’re already leery. And each time one of our prospects disappoints us, we become that much more disheartened. Until eventually we see our dates as probable losers siphoning off the remaining minutes of our lives rather than joyful additions who might brighten them.

We know it won’t work anyway, so our efforts become virtually nonexistent. It’s as if we’re at war with our own desires. We might want a relationship in theory, but we’re mired in pessimism.

In short, we are afraid to become invested

Unfortunately, our discouragement can render us unattractive. Back when I was dating, I was surprised at the number of guys who chose to spent our initial meetings going through a litany of terrible first dates, and online agonies, and failed relationships…and oh yeah, did I want to meet up again?

No, no I didn’t.

Apparently, they’d enlisted me to reassure them that they were indeed normal in a world gone mad. But it didn’t seem like they actually wanted to get to know me. They were too busy dissecting their own histories as if wondering, what did I ever do to deserve this?

Perhaps we keep our prospects at a distance because they have the power to reject us. We’re afraid of putting ourselves on the line only to be told, it isn’t enough, you aren’t enough. Or even worse, opening ourselves up to someone only to have them disappear on us. With no shared histories, there’s no accountability. After a few desertions, we might become quite bitter indeed.

Our bitterness is causing us to self-sabotage. We already know it won’t work, so we don’t even try. In preparation for failure, we offer so little of ourselves.

We fail to examine our own roles in why our past relationships ended. We just want to avoid ever being in such a vulnerable place again. And we use our intransigence to do exactly that. Our loins might be open, but our emotions are girded, our expectations virtually nonexistent, and our hearts calcified.

Our bitterness comes across as anger

I’m reading a fascinating book called I Don’t Want to Talk About It: Overcoming the Secret Legacy of Male Depression which says (warning: gross simplification) that in our society, women are raised to pull pain into themselves — we tend to blame ourselves when things go wrong. Men are socialized to externalize distress so they blame their pain on having been unfairly treated.

They tend to be insensitive to their part in relational difficulties and not to be as in touch with their own feelings and needs. But while the capacity to externalize pain protects some men from feeling depressed, it does not stop them from being depressed; it just helps them to disconnect from their own experience.

That externalization fueled some of the anger I received in response to my earlier piece about my search for a grown-up, middle-aged man. I’m guessing some of the guys who commented were still upset over past relationships, possibly the one they thought would last forever but ultimately disintegrated.

Maybe in their prior lives, they’d planted the daffodils and took out the garbage and listened to innumerable stories of bad days, but despite their best efforts, it all fell apart. And maybe they never really understood why.

So now they’re never going to do that again. And they’re not too crazy about a woman who seeks a traditional gentleman and a clean patio. (Mad power washing skills a plus).

Let’s stop being so pissed off at each other

Instead, let’s employ Shoshin, the Zen Buddhist word for Beginner’s Mind. It means to approach a situation as if for the very first time, with humility for what we don’t know and no preconceptions about what will happen. We need to have hope that we will find love. Or at least people we enjoy spending time with.

And that hope comes from believing in ourselves.

Personally, I’m thrilled to be called entitled when it comes to dating. I became vociferously entitled after several guys kept sniffing around my bikini line while simultaneously mansplaining how my relationship goals were old-fashioned. But all they had to do was leave me alone.

Trying to talk someone into bed constitutes the worst kind of entitlement

And it’s one of the reasons for my own bitterness. I’ve never tried to convince a guy that in reality, he wanted to be in a committed relationship and, oh yeah, he also wanted to clean out my roof gutters, he just didn’t know it yet.

Why would someone put down a woman for explicating her emotional wants? Wanting things is good. It means we’re alive. And it requires a measure of self-esteem to believe we can get them.

Last year, I sheepishly told a new millennial friend that I wanted to remarry eventually. “I guess I’m not much of a feminist,” I added under my breath.

But she wisely answered, “Being a feminist means honoring your wants.”

Let’s put our bitterness aside

So why settle for someone who puts little effort into being with us unless we’ve given up hope of finding anyone better? If I want to walk down the aisle wearing a bi-level, ballerina wedding dress like Stephanie Seymour in the “November Rain” video, who’s to say it’s too much?

This is a new time as we re-emerge from our homes, blink into the sunlight, and start meeting people again. Let’s put our bitterness aside to start fresh. But let’s also be sufficiently entitled to hold out for what we want, with enough hope not to sabotage our dreams.

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


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This Is How We Can Overcome the Bitterness Of Middle-Aged Dating2021-04-30T17:48:12+00:00

February 2021

What if Valentine’s Day Became “Loneliness Awareness Day”

Beach with Happy Valentine's Day written in the sand

Writing in the Sand at Santa Cruz

I’m not Blaming Valentine’s Day for All my Neuroses, BUT…

For me, Valentine’s Day has always seemed a little bit mean. Dare I say exclusionary? It’s the high school cheerleader of holidays, the one that makes you feel like you didn’t get asked to the prom.

When I was in grade school back in the seventies, Valentine’s Day meant making construction-paper envelopes, carefully wielding blunted, kid-sized scissors, smelling jars of paste, and writing our names on our creations. Our parents would buy us boxes of little heart-covered cards to distribute to our classmates. The girls giggled over the cards they got from the boys, and the cool kids got more cards. Even back then, I was not cool.

By high school, we’d moved on to sending our crushes carnations attached to little notes which were handed out during class. That way everyone could see who got the most flowers, and try to guess the senders. These little missives cost a dollar or two and were ostensibly used to fund student activities. Once again, popularity ruled. I had subterranean status in the high school pecking order and hence did not get to flounce down the hallways carrying a bouquet of carnations in varying shades of pink.

These activities remind me of the old pedagogical practice where P.E. teachers designated two, usually athletically gifted, students as team captains and allowed them to choose their own teams. Which meant they picked their friends, and the other popular kids, and the other athletes, and finally, those last few kids left behind.

I was one of those leftovers. (I was also probably the only freshman who made the honor roll, but almost got kicked out of high school for cutting P.E.)

We were taught that romantic love was quantifiable. Who wants to be the girl with no carnations who gets picked last for dodgeball?

I’m not sure Valentine’s Day is any kinder to adults.

As a baby boomer, I was taught by the media that being single was supposed to be an interim state that ended in our twenties. The goal was to wind up married, like the bridal magazines of the times which promised you “Your Best Day Ever.” (My best day was graduating from law school so I could litigate against the kind of practices that warped my childhood).

Once again, love was equated with being chosen.

I was chosen in my senior year of high school by the son of some family friends I’d known since I was seven. A college senior majoring in engineering, he became my prom date, and later my husband. Valentine’s Day was just fine, even though I kept telling him he didn’t have to buy me roses on the day itself because the prices were always inflated. But he did anyway because he was a romantic and a traditionalist. I was the girl at the office who got the big bouquet of red roses as her office-mates smiled at her good fortune.

Then my husband died.

By then, many people, especially younger folk, had stopped drinking the media Kool-Aid that happiness depended on being partnered. A relationship might be a possibility, but it wasn’t a prerequisite for a good life. Fewer people seemed to be buying into those bridal magazine layouts which, after all, are designed to sell you a bunch of stuff you’ll only use once.

But old conditioning dies hard. I’m embarrassed to admit that upon being single again I worried that I was unwantable, long past my romantic expiration date. I stressed over spending traditionally partner-centric holidays, like New Year’s Eve and Valentine’s Day, alone because that meant, in my insecurity-addled mind, that I would die unloved. Dating at fifty felt like high school all over again, except with even less dignity, if that’s possible.

Worst of all, I was lonely.

With few friends, no kids, and a family consisting of my elderly dad and step-mom, I’d sit at home at night and wonder who would notice if I suddenly vanished. “I’m alone because my husband died” twisted itself into “I’m alone because no one likes me.” I was back to being a high school nerd spending my weekend nights with Dr. Demento and an un-opened geometry book.

My loneliness equaled shameMy loneliness equaled shame, of being unwanted, of failing to have a complete life. The shame of not being chosen. Especially in a milieu where being overwhelmingly, colossally busy came with its own kind of currency - it meant you were in demand. Being a lonely, unpartnered middle-aged widow meant you were not.

I started dating so I wouldn’t be alone, ultimately winding up in an emotionally abusive relationship. My then-boyfriend was around for Valentine’s Day - along with some flowers he picked up at a freeway off-ramp - but I would have done far better to have stayed on my own.

I wanted to be able to tell people, “I’m lonely.” And “I spend too much time by myself.” And “This sucks.” But who wants to appear pathetic?

Now the world feels apocalyptic. So many people are grieving. So many of us are lonely.

This is the time for re-defining traditional expectations.

We could re-name Valentine’s day “National Self-Esteem Day” to remember it’s better to be alone than compromise ourselves by being with the wrong person. This most narrow of holidays would become a reminder of our own self-worth, which we all should have, instead of a paean to romantic love, which is far more limited and comes with its own kind of perils.

On a lighter note, we could rename it “National Onanism Day” in honor of staying safe during these times and overthrowing the kind of expectations with which I was raised. We choose ourselves. We could celebrate by taking really long showers with wonderful liquid soaps like lavender and jasmine, or CBD and peppermint. It would be far easier to celebrate when we’re all stuck at home, anyway.

Best yet might be to call it “Loneliness Awareness Day.” Maybe these isolating times will obviate the shame that comes from being lonely, and even worse, from admitting how we feel because of what others might think of us.

“How are you?”

“I feel isolated. I’m sad and lonely.” (There. Doesn’t it feel better to admit the truth?)

A wealthy, successful man I barely know recently contacted me on Facebook to say that he felt ” so damn lonely.” Apparently, he didn’t think he could confess his real feelings to his own circle. He’s an older man, and I worry for him. Maybe we could re-frame Valentine’s Day to be less about being chosen and more about removing the shame of being alone.

Really the name doesn’t matter so long as we try to help someone who feels lonely.

But first, they have to feel like it’s okay to tell us.

What if Valentine’s Day Became “Loneliness Awareness Day”2021-02-13T02:12:22+00:00

January 2021

Five Lessons I Learned from My First Date in 32 Years



Let me take you back to my first real date a year after I was widowed following a thirty-two-year marriage. I was sitting on my living room sofa with Mark, an Alec Baldwin lookalike with a gym fixation. (I’ve always had a crush on Alec Baldwin). We’d just returned from a romantic dinner and walk through downtown San Francisco holding hands.

​Red wine in long-stemmed glasses? Check.

​Fireplace crackling? Yup.

​Lights dimmed invitingly? Got it.

​It was the mythical third date. Having only met for lunch before, this was our first nighttime outing. Even more exciting, he was going to be sleeping over on that very same sofa because he lived over two hours away. I wondered whether he’d be staying on the sofa all night.

He took a sip of his wine, put down his glass, looked deep into my eyes, and said, “I need you to know something. For a long time, I’ve been really unhappy.”

​”Oh?” I replied, thinking I might be the one to bring him joy.

​”Before anything happens, I need to tell you about the woman who ruined my life.”


​He then launched into the story of an ex-live-in girlfriend who he described as an amazingly hot blonde with breast implants (not that I needed to know about her breasts) who was exactly his physical type. I also learned she’d wrecked his finances, been mean to his kids, talked him into buying a house he couldn’t afford, then cheated on him with a guy from the gym.

​”After her, I sort of lost hope,” he concluded what seemed like many, many hours later. Needless to say, we did not kiss passionately (or at all), dazed by our good fortune at having found each other.

​Mark stayed on the sofa that night.

​The next day at brunch over Eggs Benedict, he monologued about several other women who’d allegedly failed him. It was a long time before I could order Eggs Benedict again.

​The date was not a success.

​Nor was our next date which, in my inexperience, I agreed to, thinking Mark might improve over time. He did not. Even though he’d told me in our pre-date conversation that he was done talking about his past and was ready “to focus on us.” It was false advertising, and I was treated to yet another evening of the women who’d done him wrong.

​I did not see him again. But that date turned out to be a microcosm for many that followed during my years of middle-aged singledom. From it, I learned several, oft-repeated lessons.


Despite having broken up years ago with The Woman Who’d Ruined His Life, Mark still hadn’t processed his pain, causing him to turn his dates into de facto therapists. He was Robert Hays in “Airplane,” recounting his epic love story to the unwilling passengers on the plane andrelegating his dates to bit parts as his listeners.

​There are times when we are so raw that denying our pain is virtually impossible. We are our pain. It consumes our very beings. If you’d talked to me soon after being widowed, my loss was all I could talk about. No, I was not okay. (Grief therapy helped).

​But that doesn’t work in the dating world. We need to make a conscious choice whether we’ve processed our past relationships enough to take on a new one. Otherwise, we’re draining our prospects by turning them into sounding boards they never agreed to be.

​As I continued to date, I’ve met far too many men who nattered on about their exes like I was an emotional labor machine. Did they really think we were going to bond over my bashing a woman I didn’t even know? Like I was going to chime in, “What a bitch, but I get being a sucker for a hot little body. Got any pictures of her?”


​Mark acted like fate had conspired against him, first one unfaithful blonde, then another, followed by a pretty brunette (the one that got away) who wasn’t ready for love, followed by another who…you get the picture. But really, if you keep having failed relationship after failed relationship, shouldn’t you take some responsibility for them?

​I remember wanting to tell Mark, “My husband died, you just kept making really poor choices.”

​When you tell someone about all the losers you’ve been with, they’re going to wonder why you kept picking those people. (Gee, another emotionally unavailable one, why am I not surprised?) Not to mention considering whether if the way you treated them contributed to the break up. Mark was probably driving his prospects away, as he did with me, by revisiting his exes in excruciating detail. And then you’ll just be the next woman who done him wrong.

​He could have had any number of futures, but he was so immersed in the past he precluded all of them. And he self-sabotaged those futures by not allowing himself to live in them.

​When I told him I didn’t want to see him again, he acted surprised, but really, he was still living with his exes. He’d never tried to be with me.


​I think it’s the way people of my generation (middle-aged folks) were brought up. Many of us women were raised to think about how we make other people feel. We’re taught to be pleasant and unobjectionable, not to take up too much space, or raise our voices, or be openly critical. (This did not serve me well as a litigator.)

​Many of the guys got a better curriculum: they were taught to make themselves heard.

​This fails all of us in dating land.

​It looks like a first date where the guy talks a lot about himself, but neglects to ask the woman anything about her life. He may, without encouragement, pontificate on how to select the proper tires, or diversify one’s investments, or reform the United States Senate.

When he asks for a second date, he’ll be met with a polite no and a vague excuse, like “I’m so busy for the next few weeks” or “We just didn’t gel.” He’ll be bewildered since things seemed to be going so well. He won’t understand his date crossed him off because, like so many others, he didn’t try to get to know her. Her remarks were just a springboard for more self-talk.

​After his monologue on the couch, Mark concluded with, “As a widow, I know you understand pain.” But he never considered whether I wanted more heaping tablespoons of it.


​After that first evening with Mark, I never should have taken him to brunch the next day wherein I was treated to more tales of woe. And I certainly shouldn’t have agreed to another date. I had no reason (except misplaced optimism) to believe he’d be any different.

​But not having dated in many years, I trusted him when he said he was ready to focus on us. When I told him during our second evening that I was sick of hearing about his exes, he just said, “Yeah, I’ve heard that before.”

​But he hadn’t seen it as a call to action.

​I would have re-written his profile to read: “Looking for a woman to share my pain. Degree in abnormal psychology a plus. Must enjoy long walks watching me cry, romantic dinners listening to me talk about other women, and sex where I cry out their names instead of yours.”


​Dating Mark started out as a rom-com where the plucky widow, ready to find love for a second time, meets what looks like a cute, possible Chapter Two. In reality, she winds up with a guy who’s an ambulatory cautionary tale about letting go of the past.

​But maybe it was what I needed: a reminder to be grateful for what I did have, including many years with my beloved husband. In contrast, Mark showed me that spending our dates obsessing over our woes was its own form of solipsism. Our prospects haven’t signed on to fix us.

His soliloquizing also showed that we need to be curious about the people sitting in front of us. Something wonderful happens when you give someone the conversational space they need to talk about their passions. They come alive, they start to glow, and they’re thrilled to be talking to you because they feel heard. But you need to give them room to do that.

Dating offers possibilities, like the many worlds theory where different, alternative universes narrow down to one through the actions of the observer (or something like that). But you have to be open to those possibilities and to engage with your dates. Mark was basically engaging with Mark.

My first date post-widowhood was not how I wanted to learn to live in the present, but it did teach me how much we hurt ourselves when we live in the past.

(Previously published on “P.S. I Love You” on Medium).

Five Lessons I Learned from My First Date in 32 Years2021-01-09T22:47:54+00:00
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