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

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

March 2021

On Dating at Middle Age: Where Are All the GrownUp Men?

On Dating at Middle Age: Where Are All the Grown-Up Men? by @DWeissWriter #grownup #men #dating

Image from Pexels

When I started dating again after being widowed at fifty, I wondered, where are the men who act like grownups? 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 a grown man who truly cared about me, who’d be there on the days that were hard for me, like my late husband’s birthday, would listen to my worries over home repairs, and be available to talk even on the days we weren’t seeing each other. In short, I wanted a grownup.

Not the middle-aged Lothario who was still “seeing what’s out there.” Nor the guy who wanted to see me one night a week, but evaporated on all the others because it cut into his lifestyle of perpetual dating. Nor the one who thought I should sell my home and travel the world because his idea of heaven was having no responsibilities. And certainly not the ones who thought we’d get to know each other by coming over to watch movies and “whatever.”

“Whatever” is not an appropriate word for a grownup.

I discovered that the dating of my youth, which involved being invited out in advance for a planned activity, had devolved into swiping, hanging out, and hooking up. All of which felt truly pointless. Like playing quarter slots for hours. Little risk. No emotional investment. A meeting of organs instead of souls.

Love is not a dirty word.

We have every right to expect our dates to care about us. To see that we get home safely, have breakfast with us the next day if we spend the night, be straightforward about seeing us again, and make actual plans to do just that.

“Breadcrumbing,” “paper clipping,” and “pony-tail pulling” (Okay, I invented that last one) are not adult behavior.

We might have five and ten-year plans for our careers, but not our relationship goals. We might get up at five a.m. to get in our writing or running time but put no effort into really getting to know the people we’re dating.

The middle-aged, single man child is not a new phenomenon.

In the 1970s, when my widowed (it seems to run in the family) dad started dating again at forty-two, he met many women who told him he was the only man they’d met who acted like a grownup. He used to joke that he was “The Bay Area adult male.”

After five years of dating, he met the woman who became my step-mom. She was a pediatrician with a demanding job, a well-organized apartment, and a lifelong commitment to feminism. He was a homeowner, a scientist, and a truly great parent. They’ve been together for over forty years.

Going back to our carefree youth when we’re middle-aged isn’t that great.

First of all, we probably can’t. Many of us middle-aged singles have kids and homes and aging parents and health issues of our own and an eye towards retirement. Acting like we don’t is just plain delusional.

Second, we are long past the age when we should have gained some maturity. That hard-won maturity is something to be proud of, not diminished.

I meet so many middle-aged singles, failed relationships nipping at their heels, who’ve lost hope in ever finding a relationship that lasts. They contort themselves to try to seem young and carefree and, above all, disinterested. Because if they don’t appear interested, they can’t be hurt by rejection.

It’s far easier to meet up, get one’s physical needs satisfied, and scurry off afterward. But what about our emotional needs?

Let’s stop marketing ourselves as being low maintenance.

As being girls who don’t need anything when we are adult women with real needs. And hell yes, love is a need.

Being low maintenance isn’t such a great thing anyway. Having expectations means you value yourself enough not to settle for less. If someone bolts once you’ve articulated your wants, you’ve saved both of you a lot of time.

“What are you looking for?

I just want to have fun for now, heh, heh.”

Move on if you’re looking for more. “Party Hearty” is not something to aspire to.

At worst, there’s the trope of the ladette in tight jeans and a cropped football jersey saying, “I’m not like other women,” as she takes a hearty slug of her craft IPA. But really, what’s wrong with being an adult woman?

Who wants to be a fifty-something manic pixie dream girl?

For years I tried to shoehorn myself into appearing more fun than I actually am. I was embarrassed when guys asked why I didn’t like to stay out late while I wanted to ask why they never cleaned out their refrigerators. But I tired of creating a palatable version of myself that played well with others.

My idea of hot became a guy who listened when I talked about home repairs. He needn’t actually own a home, he just has to care when I fretted over mine, instead of interrupting to wax rhapsodic about the last time he was at Burning Man.

I wanted to be loved by someone who really knew me.

It took me six years to find him.

I knew my current partner was the one because he helped me choose a contractor when my air conditioner broke down in the middle of summer. That was far more exciting than a toned physique. Plus he never pushed for sex, wanted to get to know me as a friend first, and planned dates in advance — all of which indicated that he was a grown-up. For the record, he’s also a responsible condominium owner who pays his HOA dues on time.

Responsibility is hot.

I wish the media were full of appealing images of middle-aged people, other than in ads for medications and retirement plans. We go to concerts (when there used to be concerts), and buy yoga pants, and sometimes even get married again. But in the media, all the cool stuff seems limited to the young. So we aspire to seem younger and therefore, more appealing.

In their dating profiles, everyone says they love to travel. No one says they dream of remodeling their kitchen. It’s too prosaic.

But travel doesn’t necessarily make you more interesting. Nor does anything else if you can’t connect to the person you’re with. At some point, love requires the prosaic, to create the little rituals that weave our lives together as we move into forever. Seeing my partner at the sink doing the dinner dishes, as his father did for his mom, means more to me than the places we’ve visited.

Raise your hand if you’d rather remodel your kitchen than go skydiving in Ibiza. Admit to fetishes for buying new kitchen gadgets and planting geraniums. It’s cool to have your financial life in order and take care of your yard.

If you’re a woman who wants a committed relationship that leaves you plenty of time to read, then you’re like me. You just have to tell your romantic prospects. And I know in my heart there are grownup guys out there who feel the same way.

They’re probably just busy cleaning their kitchens.

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


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On Dating at Middle Age: Where Are All the GrownUp Men?2021-03-21T18:33:12+00:00
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