Final Testament of a May-December Non-Member
- Earl Fowler
- Jan 12
- 12 min read
Updated: Jan 13
Leonardo DiCaprio (age 51) is here for ‘one man bun after another’ … what a career you’ve had, countless iconic performances, you’ve worked with every great director, you’ve won three Golden Globes, an Oscar and the most impressive thing is you were able to accomplish all of that before your girlfriend turned 30. I mean, it’s just insane. — Host Nikki Glaser in her opening monologue at Sunday’s Golden Globes
Earl Fowler
Although only two-and-a-half years older than my wife of almost 40 years, I have not infrequently been accused by people who don’t know this of robbing the cradle.
When I was four, she was half my age. So I admit there’s some validity to the charge.
But mostly it arises from the fact she was born in India and has gorgeous skin and a face that belongs on the cover of Teen Vogue. As a wrinkled, old bald guy of mainly Scandinavian persuasion, I now resemble a deflated pink balloon with strong opinions.
A melted candle that somehow learned to walk. A turtle that stood up straight and started paying taxes. A bleached leather armchair left in the sun, where it gained sentience and back pain.
All of the above. Maybe even the raised thumb DiCaprio gave Glaser, though he’s obviously bored to death by jokes about his penchant for dating younger women.
Even today, even after witnessing my wife and I conversing or laughing as we walk through stores or sidle up to cash registers to pay, clerks routinely assume that we’re not together. It just doesn’t seem right. When we lived in Montreal, tourists frantically seeking directions from an English speaker would look right past me (who might have been, for all they knew, a unilingual francophone) to address the beautiful lady at my side who looked like a fresh arrival from a proper British colony.
On a visit to Cancun 20-odd years ago, we were strolling arm-in-arm past a group of chortling taxi drivers who assumed that Rekha was a local hooker and that I was her grizzled gringo client.
They shouted things to her in Spanish that neither of us understood. One of them said to me, in English, “Very good deal, sir. Almost free.”
We had walked half a block before it dawned on me what they were implying. More than implying. Rekha had been oblivious to what they were saying and simply smiled back.
That incident came back to me a few years ago when we spent a weekend luxuriating at the scenic Harrison Hot Springs Resort northeast of Chilliwack, in British Columbia’s Fraser Valley.
Apart from the family groups, a majority of the other guests were couples composed of — not to put too fine a point on it — rich old white dudes with young women half their age. Or less. Quite a bit less. Mostly Asian women from poorer countries; and of the Asian women, so far as I could tell, mostly Filipinas and Thais.
We didn’t witness any age gaps as extreme, say, as that between fossilized oil billionaire J. Howard Marshall II and model Anna Nicole Smith. Remember that slow-moving train wreck from 1994? (It had to be slow moving because Marshall was 89 when they got hitched; she was an extremely flexible 26.)
Soaking next to us in the intoxicating hot springs, the couples we saw were more in the range of Conrad Hilton, 51, and Zsa Zsa Gabor, 25, circa 1942. Or horny old Pablo Picasso and Jacqueline Roque, 45 years his junior. Or the libidinous Charlie Chaplin and Oona O’Neill (he was 54 and she was 18 when they married in ’43). Or let’s say, I dunno, Donald J. Trump and Melania (a 24-year difference in human years).
Some of these guys might have been younger than they looked, or poorer than they appeared, and some of the women might have been older and born into families that weren’t desperately poor. But if you can honestly tell me that you haven’t noticed the same, um, largely transactional pairings with increasing frequency when out and about in your neighbourhood, I’d say you haven’t been paying much attention.
Which got me thinking about the bigger picture. Never a good sign. But here we go:
So: It’s the 21st century, and as all the world’s complex, inexplicable systems of wealth and power continue to churn on their self-sustaining cycles of arbitrary and totally preposterous rules, something almost as ridiculous keeps happening: rich old men—immensely rich men, let’s be clear, think hedge-fund billionaires, owners of private islands and perpetually cranky Silicon Valley ex-gods — keep marrying women who are younger than their middle-aged children.
This isn’t a historical anomaly or an inconvenient glitch in the matrix; this is a thing. A real thing. A regular, happening thing.
And like all things that happen on a large enough scale, this trend is simultaneously amusing, tragic, slightly nauseating and definitely ironic — if one could muster the energy to think deeply about it. Which one probably should, because the layers of social commentary here are basically piled on like the discarded remnants of rich men’s tuxedos after they’ve thrown them on the floor of their $400,000-a-year hotel suites.
Let’s unpack it, shall we?
The Pros (or at least the supposed “pros”).
Let’s start with a charitable view. Rich old men, well past the usual expiration date of cultural relevance and productive skin care, often turn to these relationships to reaffirm a particularly smug and persistent worldview. The thinking goes something like this: If I can control the global economy with a single button, I should also be able to control the flow of time — or at least delay it a little, or trick it into thinking it hasn’t been speeding up for the last five decades.
And so enters the young wife or girlfriend, always a few decades younger, effortlessly cast as a symbol of the man’s virility, power and life-force. To make this work, the rich old goat must (half-heartedly) convince himself that this relationship is based on love — true, undying, romance-imbued love — because that’s what his friends at the country club keep telling him. And, naturally, the relationship does possess some superficial advantages, at least for the time being:
Social Capital: At a certain point, the rich man’s friends stop discussing his net worth and start talking about how “spry” he looks. They attribute his youthful energy to the sheer presence of his partner — never mind the fact that the woman has no idea who the Rolling Stones are, but does seem up on all the details of his offshore accounts.
A Restored Sense of Self: Nothing says “I still have it” like someone younger than your children genuinely pretending that you’re still sexy. Assuming you ever were. Sure, it’s a little scripted; sure, she’s probably not that interested in hearing about the latest market trends for vintage Fords or Led Zeppelin 45s. But the illusion works, at least for a while. Which is all most of these guys have left anyway. She’ll nod. She’ll smile. It’s like performance art ... but with less self-awareness.
That smile vanished from Anna Nicole’s face when lover boy Howie died at 90 without leaving her a dime from his $1.6-billion estate, which led to a decade-long legal battle she ultimately lost, which led to her addiction, which led to her death at age 39 in 2007. Classic American love story. Did the loathsome old petroleum tycoon, who met Smith while she was performing at a Houston strip club, orally (and I use that word advisedly) promise her half of his estate, as she claimed? Yeah, probably. But so what? He got what he wanted and went out with a smile on his face. That’s the one that mattered to him. Relationships like this are forged in an imbalance of power.
A Guilt-Free Audience: It’s an unspoken truth that rich men, once they’ve crossed the threshold of their third or fourth marriage, appreciate the ability to keep their “audience” impressed. “Look at me! Still attracting the eye of younger women! I have not become irrelevant!” It’s the billionaire’s version of a trophy wife — except, you know, it actually works in an amusing way. Because most women his own age can see through the bullcrap, but the younger wife can still be enraptured by him — or at least, by the yacht. Or at least, that’s the hope. And it’s not just the beauty of young women or the coin vaults of the Scrooge McDucks of the world that are at play here.
Writer Zoe Williams hit on something important, I think, in an essay that ran in The Guardian in 2019:
There is a maximum number of times a woman can get annoyed about what a French intellectual thinks about her arse. I thought I’d hit it in the 90s, when Michel Houellebecq did an elaborate, 300-odd page analogy between sexual liberation and free-market capitalism, which concluded that women were destroying men’s dignity. It was a hard-left version of Jordan Peterson that was, if you can possibly imagine such a thing, even more annoying.
Yet when the novelist Yann Moix announced this week that 50-year-old women were too old to love – “The body of a 25-year-old woman is extraordinary. The body of a woman of 50 is not extraordinary at all” – I felt that old and delicious indignation. It’s not the talking-about-us-like-we’re-meat. It’s not the generalisation, or the brass neck of a guy who is 50 himself, and about as extraordinary to look at as an upturned shopping trolley in a canal. It’s just dishonest. There is nothing more contemptible than a home truth that isn’t true.
Men don’t like younger women because their flesh is firmer but because their opinions are a bit less firm – or at least that’s the hope. Anyone 20 years younger than you tends to assume you’re right about most things. Some men will trade in a lot of shared cultural reference points for a bit of admiration. Likewise, the cliché is that young women date older men because they are richer, whereas nearer the truth is that they seem to know a lot of useful stuff.
The Cons. Oh, Yes, There Are Cons. (Speaking of Don and Melania.)
Now, let’s try to inject some reality into the mix. While the rich old man might be receiving high-fives from his equally rich buddies (some of whom have, of course, their own trophy wives tucked neatly into designer handbags), there’s also the little matter of how this whole thing plays out when we apply actual human logic. And this is where the plot thickens. Not all aspects of this arrangement go according to plan.
Your Children’s Existential Crisis: Imagine being the middle-aged child of a wealthy old man, having worked through the embarrassment of his multiple divorces, only to arrive at a family reunion and find that your father’s new partner is younger than you. It’s the kind of situation that leads to major, major life questions. Do you laugh it off? Pretend it’s a new season of Stranger Things? Or — here’s the best option — get yourself a nice glass of wine, sit back and watch your father’s new wife interact with you — trying to figure out if you’re her contemporary, a rival or more of a “mentor” in a panel of that long-running newspaper comic strip Bringing Up Father. (Not that she or the middle-aged child would ever have heard of Bringing Up Father.)
The Glaring Discrepancy: It’s hard to overstate how awkward it must be when this new, fresh-faced woman, who still believes in things like personal growth and metaphysical well-being through yoga, tries to engage with the man’s peers — i.e., his actual age group. Because while he may be purchasing $5-million paintings in private auctions, she is usually finding herself being introduced to 70-year-old women who insist on asking her what shampoo she uses, which is about as uncomfortable as it gets. No one is asking the young wife to produce a convincing emotional response to the question “So, have you read Proust?” because she probably hasn’t (and neither have they) — but everyone’s pretending, for the sake of propriety, that she’s the intellectual equal of the 73-year-old hedge-fund manager. She can’t be. Not right away.
Thing is, that gap in knowledge and experience tends to close pretty quickly, along with the window for esteem and adulation that the old buzzard was seeking in the first place. Remember what Williams was saying about impressionable young women being wowed by the knowledge and experience that successful older men bring to the table? This was her experience of being in a couple of relationships with greybeards while in her twenties:
And they do know a thing or two, older people. They know what to order, why the washing machine is broken, how to drive, how to peel garlic. But very quickly you get used to what they know, and are often astonished by what they don’t know, and your admiration and credulity gives way to a more peer-to-peer style relationship. Shortly after that, it ends. When you’ve signed up for an admirer, the last thing you want is someone who takes the piss like everyone else and can’t pick Lemmy out of a line-up.
The Grand Delusion of Forever Young: So sooner or later, reality hits. Because while it may seem great to have a partner who is under the age of 40 when you’re in your 60s or beyond, this concept inevitably runs up against the biological clock. What happens when she hits the wall — or, more terrifyingly, when he really hits it? A lot of these rich old duffers have convinced themselves that age is just a number — until it’s not. The golf outings, the big social events, the parties in the Hamptons — none of these events are immune to the subtle clockwork of time. Sooner or later, the sheen wears off.
Jokes Among Friends (Hint: Not All Are Kind)
Of course, the pièce de résistance of this whole charade is the rather uncharitable commentary that occurs when the rich old man and his young wife are not around. He may not care what her friends think. But she will. And his, sipping their aged whisky in some extremely elite venue (probably on an actual yacht), will begin the inevitable ritual of discussing the Henry Higgins-Eliza Doolittle “relationship.” You know, just a little I’ve-grown-accustomed-to-her lace gossip, a bit of how’s-your-father-figure banter among peers who all know something is disastrously creepy about the situation, but also acknowledge that no one’s likely to say anything. To his face.
Cue older men approaching younger women in the lounge jokes:
Him: Where have you been all my life?
Her: For the first third, I was a gleam in my grandpa’s eye. For the second, in my dad’s. Then there was preschool, kindergarten, Girl Guides ...
Him: It’s only fair to tell you, trouble is my middle name.
Her: Yeah? So what’s your first name? Prostate?
Him: Experience matters in bed.
Her: Not as much as circulation.
Wocka wocka wocka.
There is, of course, nothing new in any of this. Think of those two old lecherous judges in the Book of Daniel who spy on the virtuous young Susanna while she’s bathing, then attempt to coerce her into sex. Think of Ovid’s Metamorphoses, an ancient narrative poem that features several instances of crusty male gods pursuing vulnerable nymphs. Mythologized predation. Only there’s nothing mythological about it.
Shakespeare’s The Merry Wives of Windsor shifts the emphasis slightly by making the aging lecher an outsider rather than a husband. Falstaff imagines himself irresistible, but his fantasies are inflated versions of the same old-man delusion: that status or rhetoric can replace youth and mutual desire. The women conspire to humiliate him repeatedly, turning the male gaze back on itself. Importantly, Shakespeare’s comedy grants the women moral and intellectual superiority without casting them as tragic victims. They enjoy the joke; Falstaff endures it.
Literature all over the world bursts with such examples. Unlike tragic versions of the trope, comic treatments do not ask us to pity the old man deeply or condemn the young woman harshly. Instead, they reaffirm a comic worldview in which rigidity loses to flexibility, fear to pleasure and pretension to wit. Not that any of the players in these varied demographics, I suppose, would object to a little more rigidity and a little less flexibility. (I mean, so I hear.)
The joke is enduring because it stages a universal anxiety — aging, loss, sexual competition — and renders it survivable through laughter. Comedy does not deny cruelty or imbalance, but it insists that those who mistake possession for love deserve, at the very least, to be laughed at.
And in short, there’s no fool like an old fool.
Conclusion
Still. Let’s not forget that other old adage: He who laughs last, laughs best. What we’re really talking about here is more than just a rich old man with loose skin and clammy jowls flaunting a young trophy wife at the Rotary Club. We’re talking about an ancient paradox — about wealth and power, about the creation of narratives to obscure the obvious absurdities of life and about the extreme lengths people will go to for affirmation that they’re still desirable, relevant, and — why not? — able to get away with a good joke among their equally ridiculous friends.
As I strolled through the well-appointed Copper Room at the Harrison Hot Springs resort (limited seating, reservations required, live entertainment, $58 10-ounce steaks) — receiving the odd nod of approbation and conspiratorial wink from wealthy retirees who assumed I was part of their friend group — I couldn’t help reflecting on what a bubbling bouillabaisse of privilege and inequality this all seemed. What a tottering bricolage of late-life lust, unmindful arrogance, irritability, imperialism, citizenship papers, money sent home to families in poor countries, back rubs, front rubs, statins, stents, Voltaren, compromises, erectile dysfunction drugs, cold-hearted calculation, plotting, empathy, loathing, resignation, physical aversion, genuine affection and maybe even (anything is possible) instances of love.
The rich old man who marries the callipygian younger wife is, in his own way, a symbol: not of eternal youth, but of the will to live inside an illusion — a fragile illusion, precariously balanced on an offshore account and a well-fortified ego. It’s a funny thing. It’s absurd. It’s ironic. But really, when you think about it, it’s also just another example of how rich people always manage to have the last laugh.
What was it that a classic typewriter exercise of yore taught us about these relationships all those years ago? Oh yeah. The Quick Brown Fox Jumps over the Lazy Dog. Only here in the Copper Room, it’s the other way around.
Eliza, where the devil are my slippers?

Having witnessed a stodgy old British buzzard bringing back a much younger woman from the Philippines,
and having one of her daughters slip up at her memorial as to the economic nature of said relationship, something along the lines of now we will starve because momma will not be sending us his money anymore…I thought, don’t worry, as repugnant as this old bodger is, you can be his next spouse.
I was somewhere in-between bemused and disgusted. More at buzzard boy than anything else, really.
Shopping for foreign brides.
She likes me, she really does.
Uh huh. Nooo doubt.