All the Young Dudes
In which I inadvertently discover that at almost 60 I can still "get It" despite what the culture (and some exes) would have me believe. Random thoughts on older women + younger men, and vice versa.
With just over an hour to kill before the book discussion I’d be taking part in at Book Club Bar in the East Village, I took myself to dinner at Superiority Burger. The place was mobbed, but I was in luck; they had an open seat at the bar.
I enjoy eating alone in restaurants, especially crowded ones—something I did all the time when I lived in the city, and haven’t been able to do as much in my life upstate, especially not since the pandemic killed all my favorite, buzzy social hubs—establishments where, on a given evening, I could count on bumping into any number of friends and acquaintances.
I find there’s a life-affirming electricity in dining solo among many, intermittently reading, people-watching, and eavesdropping.
Even better if you can dine at the bar and make light conversation with others out on their own.
***
Before I tell you some ageist/sexist things old boyfriends said to me, let me get this out of the way: I’m deeply embarrassed by my relationship history prior to the one I’m in now—a happy marriage of twenty years and counting.
Surely you’ve encountered the curious phenomenon of smart, feminist women getting mixed up with chauvinist pigs? It always mystified me when I observed it in other women, despite an unfortunate tendency toward it myself.
But the things they said didn’t only reflect badly on them. They were reflective of attitudes deeply held in our culture. My exes were merely saying the quiet parts out loud. That’s why their words matter enough for me to tell you about them.
***
I was seated at Superiority Burger’s bar, looking at the menu, when the cute young guy to my right leaned over and asked, “Have you been here before?” I hadn’t, but had been meaning to for some time. “Everything’s good,” he insisted. He was eating the Yuba Verde sandwich made with a chewy tofu “skin” produced when you scald soy milk. “This is fucking amazing,” he said, pointing to the sandwich. I took the recommendation.
***
Okay, here goes. When I was 32, a 35-year-old boyfriend took me for a walk to inform me I’d grown too old for him, and on that basis, broke up with me.
When I was 35, a 37-year-old boyfriend—when he was in his cups—repeatedly assured me of the following:
When we’re older you’re going to stop being attractive to men, and I’m going to keep being able to get women, even really young ones.
He said it semi-jokingly, ha ha.
Twenty-five years later, that “joke” still lives rent-free in my head.
***
As my bar-mate ate his dinner and I waited for mine, we kept talking. The conversation was breezy, and natural—so easy and familiar I wasn’t sure whether he was flirting.
Tall, brown hair, brown eyes. Bit of a shnoz. (Complimentary.) I clocked him as around 35. Maybe 37. Definitely not 40.
Hard to tell. The restaurant was dimly lit, particularly toward the back, where the bar is. Maybe he couldn’t see that I have a full head of gray hair. That I’m almost 60. That I was wearing a wedding band.
What did it matter? We’d part ways soon enough, and he was good dinner company.
***
When I was 35, a 37-year-old boyfriend, when he was in his cups, repeatedly assured me of the following:
When we’re older you’re going to stop being attractive to men, and I’m going to keep being able to get women, even really young ones.
He said it semi-jokingly, ha ha.
Twenty-five years later, that “joke” still lives rent-free in my head.
***
Last month in Oldster Magazine I published an essay by Gail Rice about hiring a 40-something escort for her 70th birthday. The piece was quite popular, and most readers responded positively—a rousing chorus of “You go, girl!”
But privately a few people, whom I’d assumed were broader-minded and more evolved, had less generous takes. One man was perfectly scandalized, even by just the idea of a 70-year-old woman being interested in having sex with anyone, let alone a man 30 years younger. I was too taken aback and disappointed to argue.
Besides, I knew where it was coming from. I talk a good game about standing up to ageism and sexism, but I’m also deeply infected by those twin evils, and often surprised by my own ageist and sexist assumptions. Like everyone, since birth I’ve been marinating in a culture polluted with bigotry of every stripe. It’s nearly impossible not to absorb some of it.
Maybe I do the work I do—publishing a magazine about aging—as much to counteract the harmful thinking I’ve internalized as to counteract it in others.
***
When he finished his sandwich, the young man ordered a scoop of carrot sorbet. “Carrot sorbet?” I asked.
“Can I get an extra spoon?” he asked our server.
“You have to try this,” he said when it arrived. “Their gelatos and sorbets are mind-blowingly good.” I sampled his dessert. He was not wrong.
***
In the fall of 2022, I published an essay in Yes! magazine entitled “All the Sexy Older Ladies,” about positive representations I’d begun seeing of older women in movies like Good Luck to You, Leo Grande, and television shows like Queen Sugar, Hacks and Killing Eve. In all of those, women in their late 50s and 60s are shown, respectfully, as sexual beings. They all get it on with significantly younger partners, in all but one case men.
I published the piece when I was 57, and found what I’d observed to be inspiring, especially as a woman approaching 60.
What’s more, it was a perfect fuck you to that ancient refrain still ringing in my head, and the dude who’d planted it there.
***
When we’re older you’re going to stop being attractive to men, and I’m going to keep being able to get women, even really young ones.
Don’t count on it, Bud.
***
I talk a good game about standing up to ageism and sexism, but I’m also deeply infected by those twin evils, and often surprised by my own ageist and sexist assumptions. Like everyone, since birth I’ve been marinating in a culture polluted with bigotry of every stripe. It’s nearly impossible not to absorb some of it.
Maybe I do the work I do here at Oldster as much to counteract the harmful thinking I’ve internalized as to counteract it in others.
***
The young guy next to me at the bar asked what I was up to the rest of the evening. I told him about the discussion I’d be part of at the bookstore, which was related to my New York City essay anthologies.
He was intrigued—especially given what he did for a living; he worked for a major real estate firm, referred to himself as “a marketing executive” there.
Okay, maybe 40. Still, almost 20 years my junior.
***
When I was 36, I dated “Zach,” a man who was 30. I referred to him as “my 9/11 boyfriend,” because I’d met him at a vigil a few days after the attacks. We were enough of a mismatch that I assumed from the beginning the relationship was temporary, and defined it by the circumstances under which we’d met.
In light of that assumption, I disregarded our age difference (and our many other glaring differences) because it seemed the world was ending so what did anything matter anyway? He was also awfully attractive, and kinder to me than anyone I’d ever dated.
We were together on and off for more than two years, way too long for what should have been a fling.
The whole time I stood on high alert, waiting for the other shoe to drop. Surely, at some point, he’d ditch me for a younger woman.
I was right. I just hadn’t guessed how casually, and how young. When he asked my opinion as to whether his playing Spin-the-Bottle with some recent college grads (then making out with one of them) constituted cheating on me, I felt like Elizabeth Perkins in Big, and knew it was past time I move on.
***
I’m not sure our chronological age difference was to blame so much as our emotional age difference. I’ve since witnessed several instances of older women having great relationships with younger men.
Recently a close friend got married for the second time, at 60, to a man she describes as the love of her life, 51. Their mutual joy has been undeniably evident since the moment she introduced me to him three years ago. (Just about all the men she dated after her divorce were younger.)
Eighteen years ago I introduced another friend to a man eight years her junior. They’ve now been married for sixteen years. She’s 61; he’s 53.
***
At 37, after “Zach” and I broke up, I busied myself with online dating. My biological clock was ticking, and I didn’t yet know I couldn’t have kids. (I also had yet to let myself in on the secret that I didn’t want them.) My therapist had put me up to it, and I really applied myself to the assignment: I went on roughly 60 dates in nine months.
I was surprised by how many older men shaved years (sometimes a decade or more) off their ages in their dating profiles. But I was utterly shocked when I found myself on a date with a 29-year-old who’d padded his age by six years.
“Let me first confess that I’m actually not 35,” he said when he greeted me at Cafe Centosette (RIP), one of my neighborhood go-to spots for internet dates.
He was an actor and an aspiring filmmaker. Model handsome, tall, blonde, blue-eyed, gentile with a capital G, from the Midwest, and obsessed with New York City culture. He tried to impress that upon me by sprinkling his patter with lines from Woody Allen movies and mispronounced yiddishisms.
It was kind of adorable, and reminded me of when Harrison Ford, playing a bank robber in the wild West in The Frisco Kid, says to Gene Wilder’s Polish rabbi, “You’re a real mish-e-GOO-nah.”
He was surprisingly into me.
Surprisingly. Uh-oh, my internalized ageism is showing. Also, my looksism. I am not conventionally attractive—I consider myself “thinking-man’s attractive” at best. Short, curvy, soft. A nice but unremarkable face. I detected an asymmetry between us I might not have if I didn’t live in a culture obsessed with certain looks and features passed down from one generation of pale caucasians to the next. It wasn’t just me though—a friend once commented on my “surprising” ability to attract conventionally handsome men. (Thanks, “friend.”)
His interest in me was flattering as hell, I’ll tell you that. But given that I was just getting over a then-32-year-old, and that clock of mine was ticking, I was reluctant to move forward with another younger guy.
That, and he rarely got my cultural references. It was exhausting to have to bring him up to speed on so many things.
“You’re too young for me,” I kept telling him, from the first time we went out.
“That’s so silly,” he insisted. Was it?
After the fifth date (a good one), I broke things off, and he shocked me again, by crying.
“It’s good that you’re older!” he protested through tears and snot. “You can show me things! I can learn from you! We can learn from each other!”
It made me want to write a version of Pygmalion—I mean Annie Hall—with the genders reversed.
***
I’ve since witnessed several instances of older women having great relationships with younger men.
Recently a close friend got married for the second time, at 60, to the love of her life, 51. Their mutual joy has been palpable, since the moment she introduced me to him three years ago. (Just about all the men she dated after her divorce were younger.)
Eighteen years ago I introduced another friend to a man eight years her junior. They’ve now been married for sixteen years. She’s 61; he’s 53.
***
When we’re older you’re going to stop being attractive to men, and I’m going to keep being able to get women, even really young ones.
You sure about that, my friend?
***
The younger guy to my right looked at his Apple Watch, then asked for his check.
***
In the summer of 2013, my husband and I were having dinner together at the bar on the back deck of Boitson’s (RIP), one of those buzzy social hubs in Kingston I now desperately miss. We were seated next to (since-deceased) playwright, poet, and actor Sam Shepard, and to respect his privacy, pretended we had no idea who he was.
He overheard us talking about a bear we’d nearly run over after it darted in front of our car on Rt. 32, and he chimed in. “I saw a bear around there today, too!” he said. “I wonder if it was the same one.”
Sam Shepard was making small talk with us. I nearly died.
He was in town shooting Cold in July, and his costars, Don Johnson and Michael C. Hall were also out on the restaurant’s back deck, having dinner together at a table with a view of the Catskills.
During a pause in our conversation, Shepard excused himself to make what turned out to be a booty call. Ten minutes later a 20something waitress we recognized from a local restaurant showed up and joined him.
Back home afterward, Brian and I noted how much she looked like Patti Smith, with whom Shepard had been involved as a much younger man.
We also totally judged him.
Two days later, on the Trailways bus to the city, I found myself seated a row ahead of the 20something woman and her friend. I overheard her say the sex was okay, “But his skin was so crepe-y!”
“Ewww!” her friend replied.
I had half a mind to turn around and set them straight. That’s Sam Fucking Shepard you’re talking about! And he is fine! He was 69 at the time. (He died four years later, at 73.)
The other half of my mind reflected on how, not long before that, Shepard had ended his marriage to Jessica Lange, then 64 (now 76). I was right back to judging him.
The words “age-appropriate” popped into my head. Now I wonder about that term.
Another term, “double-standard,” just occurred to me.
***
It’s kind of a miracle my husband Brian and I met, and a fortunate one at that. There were many obstacles to our finally connecting that I won’t go into here, but I’ll share this one: Despite really liking his dating profile, I almost didn’t reach out to him on Nerve Personals strictly because he was 41.
I was 37—just three years and eight months younger than Brian, to be exact. It seems utterly ridiculous now that I would have hesitated. But in my 30s, I had this idea that…Jesus Christ, Sari…that…okay, I’ll just say it: that men in their 40s smelled and had bad breath.
I thought, Am I really going to go out with a guy in his 40s?
Me. Now the Oldster lady. The one who’s so busy trying to get us all to expand our minds and challenge our assumptions and throw away old “shoulds” when it comes to age and aging. I thought that. 🤦🏻♀️
I met him and discovered how delightfully boyish he was—is—while simultaneously the most emotionally mature and emotionally intelligent man I’ve ever known.
It bears mentioning, though, that in person he did not appear quite as boyish as he’d looked in his profile picture, for which he’d dyed his graying beard.
He’d been afraid some women on the dating sites wouldn’t give him a shot if he appeared too old.
Interesting.
***
When I was writing last Friday’s Oldster Link Roundup, initially I included Liam Neeson’s and Pamela Anderson’s ages when introducing Alyssa Bailey’s Elle piece about how they’re now dating at 73 and 58, respectively. I felt weirdly protective of them, and didn’t want people commenting negatively on their age difference.
Why did I care? Don’t I encourage people to be open about their ages? Don’t I, in a professional capacity, celebrate intergenerational relationships of all kinds? I went back and forth, but ultimately deleted the numbers.
I’m not sure what this says about my internalized ageism and sexism, but probably something.
***
It’s kind of a miracle my husband Brian and I met, and a fortunate one at that. Despite really liking his dating profile, I almost didn’t reach out to him on Nerve Personals strictly because he was 41.
In my 30s, I had this idea that…Jesus Christ, Sari…that…okay, I’ll just say it: that men in their 40s smelled and had bad breath.
I thought, Am I really going to go out with a guy in his 40s?
Me. Now the Oldster lady. The one who’s so busy trying to get us all to expand our minds and challenge our assumptions and throw away old “shoulds” when it comes to age and aging. I thought that. 🤦🏻♀️
***
The young guy to my right paid his bill. “Before I go…can I get your number?”
Whoa! He had been flirting.
I picked my jaw up off the floor and composed myself.
“Well,” I said, “a) I’m married, and b) I don’t know about you, but I’m kind of old—59.”
He looked genuinely stunned. “No way!”
“Way!” I said, and we both laughed. “Like, I was born in 1965.”
“Oh, my god, I’m so sorry,” he said.
“It’s okay!” I insisted. “I’m flattered.”
He thought for a second. “My parents were born in ‘64 and ‘66.”
“Holy shit,” I said. “How old are you, if you don’t mind my asking?”
“I’m 27.” He covered his face in embarrassment. “Born in 1998.”
“Oh, my god,” I said, “in 1998 I was traipsing around this neighborhood with a string of Peter Pans.”
We both laughed, and then he was on his way.
***
At the book event, I couldn’t stop myself from telling everyone that a 27-year-old had just tried to pick me up.
***
When we’re older you’re going to stop being attractive to men, and I’m going to keep being able to get women, even really young ones.
Okay, now it’s funny. I’m the one who’s laughing.
***
In “The Click,” Season 2, Episode 6 of Hacks, Jean Smart’s character, Deborah Vance, meets a much younger man at a bar and goes home with him. At the time of filming, Smart was 71, and Devon Sawa, the actor playing Jason, the younger man, was 44.
When Jason first hits on Deborah, she asks, “What, do you have a fetish for older women?”
“I guess I do,” he says. “I like older women, is that a bad thing?”
At almost 60, I’m going to go with “No.”
At 44 I met a man I’ve been talking/flirting with for over a year on Twitter. The attraction was instantaneous but…he was 29. A 15 year age difference especially at those life points seemed insurmountable.
I thought he’d want babies (I did not and could not). I thought he’d want a woman his age. I figured it would be a fling. Five months later we were still dating. When I said, “I guess we’re in a relationship”, he casually replied with a smile, “We have been for five months.”
13 years later we’re still together, married for 7. I do worry about being a burden to him as I age. Still, it’s the happiest relationship I’ve ever been in.
Wonderful piece. It's not just the ageist bias we encounter; it's also the ageist bias we bring to the party. And the Sam Sheppard story and the girl on the bus is a reminder: Be careful what you say in public. A writer may be sitting next to you.