As far as Hefner was concerned, he was offering women feminism the way it should be. Being a bunny was a way to move beyond prissy morality and claim sexual empowerment. “Women were the major beneficiary of the sexual revolution,” he told Cosmopolitan in 2015. “It permitted them to be natural sexual beings, as men are. That’s where feminism should have been all along.” That was a self-serving definition from a pornographer, but it was one that some women embraced: if feminism was about a woman’s right to choose, they chose to commodify themselves for profit.

But the obituarist was more right about Hefner’s timing than she could have known. Eight days after his death, the same paper published its devastating expose of Harvey Weinstein’s serial sexual assaults against women, and the #MeToo movement quickly assembled in response. You can’t exactly call it luck when a 91-year-old dies, but if Hefner had lasted two weeks longer, the memorials would have been far harsher judgement about his influence on the 20th century.

#MeToo was, broadly, about sexual harassment; but specifically, it was about the fact that sexual harassment could happen even in industries where women’s sexuality was treated as an asset to be exploited, even in circumstances where a woman might cynically be said to have profited from the encounter. Leveraged consent was not consent. A choice made under pressure was no choice at all.

Perhaps Hefner had sensed the coming reckoning. Six months before he died, he summoned Crystal Hefner — his third and last wife, 60 years his junior — to his bedside, and made her promise to “only say good things” when he was gone. Crystal agreed, but the deathbed setting, the frail old man desperately trying to extend his powers beyond mortality? That belongs in a book — and now her promise is the title of Crystal’s memoir, in which she very much does not limit herself to saying only good things.

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Life in the Playboy Mansion in the late Noughties, she writes, was controlling and transactional. A strict 6pm curfew applied to Hefner’s girlfriends; in exchange for performing regimented group sex, they got bed, board and $1,000 cash a week. To her credit, Crystal is frank about the reason she and other women entered into this high-gloss servitude. When she first visited the mansion for a Halloween party in 2008, she was 21, and Playboy promised impossible glamour and riches. “That ornate front door looked like the doorway to success, to a place that could make all of our dreams come true.”

If you became a girlfriend, you might be able to become a playmate, with a centrefold in the magazine. If you became a playmate, you might be able to parlay that into the kind of fame that Pamela Anderson or Anna Nicole Smith had achieved. Implicit was the assumption that the bad parts of these women’s stories — the stolen sex tape that humiliated Anderson, the drug addiction that killed Smith — could be skipped. In the economics of choice feminism, the undesirable costs of sexualisation were outsourced to the sexualised, never accounted for. Hefner’s mini-harem were forever kept in check by the threat — as Crystal puts it — of being replaced “by another woman with blonder hair, better breasts, and a better nose”.

Hefner had always had a type, going back to the very first issue of Playboy in 1954, which flew off the shelves on the basis of a nude Marilyn Monroe pictorial: slim, fair, busty. Anderson fit this mould, and so did Smith. But whereas in his prime Hefner had made some room for variation — he was, along with everything else, a committed anti-segregationist — by the time Crystal was in the picture, that type had calcified entirely. Photos show him flanked by eerily samey women: femaleness as an entirely fungible commodity. Their hair, breasts and noses all converge onto one ideal, which is to say Hefner’s ideal. This was a work of art as well as nature. When Crystal decided to upgrade her appearance, she went to “the plastic surgeon who did all of Hef’s girls”.

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When multiple women “chose” to turn themselves into Hefner’s fantasy, the result was a brutal kind of physical competition, in which the body itself was remodelled to approach an impossible physical standard — and to demonstrate their loyalty to their master, who was not such a fan of “natural sexual beings”. Women could work within the system and even achieve short-term gains, but the toll of being an object was borne by the flesh.

The women of Playboy were rational actors, certainly, but they were acting in a tiny ecosystem governed by the whims of one man. “Nobody likes a prude, Hef would say, and I could make your own choice about whether to stay or go,” writes Crystal. “After I’d been there for a while, it didn’t feel like much of a choice.”

By this time — the late Noughties — Hefner had become a victim of his own prescience: the America of the 21st century was one he had helped to create, which meant his product no longer stood out. In a Playboy world, who needed to buy Playboy? Nudity was readily available online: why pay for softcore pictures when you could get the hardcore stuff for free? It’s symbolic of how exhausted the Playboy concept was that Hefner ended up selling his mansion to a fan from under himself before he died.

All that was left, really, was the brand. And the obvious way to make money from a brand in the 2000s was to turn it into a reality show. The Girls Next Door had been running for three years when Crystal arrived, stepping into the show as Hefner’s girlfriend number one, although not particularly successfully. As she admits in the book, she was “wooden and quiet”, although in her defence, she wasn’t being paid to be compelling. The deal was between the network and Hefner. He got $400,000 an episode, despite barely appearing. The girls — the stars — got nothing. “It didn’t even occur to me that it wasn’t a fair arrangement,” says Crystal. “I just felt lucky to be there.”

This seems like an extraordinarily unworldly thing to believe, but people — women — who felt “lucky just to be there” were foundational to large chunks of the Noughties economy. It was why girls went wild for Girls Gone Wild, even though they received no more than some cheap beads in exchange for flashing their tits. You could take your portion of the sexual revolution, only if you acceded to it happening on men’s terms.

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Hefner was a pioneer here as well: he built his empire directly on profiting from women’s bodies without sharing the rewards. Anderson has said that being a playmate was “empowering”, but not so much in the financial sense. It launched her career, but in her 2023 Netflix documentary she says she didn’t get a cut from any of the calendars or videos that Playboy sold off her back. And those Marilyn nudes in the first issue? Bought from the photographer for $500. Monroe herself got nothing — a fact that was once seen as proof of Hefner’s business acumen.

And yet, if Hefner was the master of timing, his widow’s book comes too late. Crystal’s isn’t the first book not to “say good things” about Hefner. In 2015, Holly McKenzie — the number one girlfriend before Crystal — wrote her own memoir of the “betrayal and abuse” she experienced in the mansion. In 2013, Jennifer Saginor — daughter of one of Hefner’s best friends — published Playground: A Childhood Lost Inside the Playboy Mansion. Since 2022, the documentary series Secrets of Playboy has racked up an exhaustive 20 episodes. At this point in the #MeToo cycle, the victimisation of women like Crystal is well established.

In fact, she’s told the unflattering story of her time in the Playboy Mansion already — in, among other places, an interview with Howard Stern in 2011, when she and Hefner had temporarily broken up. In the book, Crystal refers to that episode regretfully, saying she “let Howard Stern coax me into saying cruel things about Hef” and “felt awful about it after… like I’d lowered myself even further into a pit of shame and regret”. Yet all she did was share the same truths she’s sharing here — describing the same rigid rules and squalid sex — in a now-unfashionable register. In 2011, she was playing the part of the shameless vixen. In 2024, she’s playing the part of the woman-child, “a kid who went trick or treating somewhere and never left”.

The truth, probably, is somewhere in between. Hefner used women, but he was only able to because women like Crystal believed they could use themselves to extract money and power from the Playboy institution. Part of the genius of choice feminism, from the male point of view, is that it makes women complicit in their own exploitation. Crystal never approaches those subtleties: she says she felt trapped, but then can’t fully articulate why, having broken her engagement to Hefner, she returned to become the last Mrs Hefner.

But it’s the subtleties that would make her interesting. I know Hefner was a goat and a shark. I would much rather read an honest account of the political acumen it takes to become the chief girlfriend, and eventually the wife, of a professionally promiscuous and very wealthy man. But in that sense, at least, Crystal chose her moment perfectly: as his widow, she’s probably the only woman to have made more money from her bargain with Hefner than he made from her.

West Elm Caleb reportedly slept with a lot of women via dating apps, and wasn’t very honest with any of them about what he was doing. Then some of his dates compared notes via TikTok and the result caused so much arguing it was even reported in India.

Why all the noise about some two-bit Lothario in a city a long way away? Well, in one sense, this is as old as humans: the ongoing resonance of mythic figures such as Helen of Troy show we’ve been quarrelling about men, women and sex for a very long time.

But the contours of the argument are also uniquely modern. It concerns a dream of hedonistic freedom that blossomed in the mid-20th century, and that Greer herself helped to articulate. And it also captures the way that dream has soured in the hyper-mediated 21st-century world.

In The Female Eunuch, Greer argued that men have, since time immemorial, stuffed women into a domestic role, in which we’re treated variously as drudge and sexual object. In Greer’s inimitably pithy terms: “a receptacle into which he has emptied his sperm, a kind of human spittoon”.

In turn, she thought, women have internalised a stunted image of our own desires. While our bodies are different, supposedly immutable differences in our inner lives are really imposed by stereotype. And this stereotype serves to “castrate” women, replacing a fully engaged and emancipated “female energy” with a weak and artificial “femininity”.

Greer argued that women should abandon this self-imposed prison. Instead, we should pursue “revolution” – meaning the “freedom to be a person, with the dignity, integrity, nobility, passion, pride that constitute personhood”.

Five decades later, how is Greer’s vision working out? Well, the Anglosphere rejection of suburban domesticity and motherhood is now advanced. The average age of marriage has been rising steadily since the Seventies, while the total number of marriages has declined steadily. Over the same period, birth rates in the US and UK have fallen steadily and are currently at their lowest ever level.

“Childbearing was never intended by biology as a compensation for neglecting all other forms of fulfilment and achievement”, Greer argued. And now that women have more choices, claims feminist Jill Filipovic, we’re voting with our feet (or, perhaps, wombs).

So Greer’s vision of swapping compulsory domesticity for greater female choice, self-realisation and empowerment has been realised, at least for some. But how far did she really swim against the tide in setting this out?

When The Female Eunuch rocketed Greer to international fame, the Anglosphere had already seen a decade of “counterculture”, centred on the rejection of tradition and the pursuit of freedom and desire. And one crucial text for this was Jack Kerouac’s On The Road (1957) – a book that, like The Female Eunuch, celebrated the freewheeling pursuit of passion over the humdrum everyday.

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The central character, Dean Moriarty, is a drifter, a slacker and a hedonist. He floats from place to place, leaving a trail of unpaid debts, disappointed friends, damaged cars and chaos in his wake. He’s also a prolific and faithless shagger, taking up with (and sometimes impregnating) lover after lover before abandoning them – in one case with a newborn baby.

In Kerouac’s telling, Moriarty is depicted both as a walking disaster zone but also an ecstatic, spiritual figure. Far from being abusive, his womanising seems animated by an intense desire to drink deeply from the cup of life, love and desire:

He darted the car and looked in every direction for girls. ‘Look at her! […] And dig her!’ yelled Dean, pointing at another woman. ‘Oh, I love, love, love women! I think women are wonderful! I love women!’

Kerouac celebrated Moriarty’s unthinking and often-callous spontaneity as a kind of saintliness. Greer’s innovation was to lay claim, on women’s behalf, to a countercultural movement whose main characters had hitherto been mostly male.

For her vision of revolution also involved women becoming more Dean Moriarty-like. Women, she claimed, “are not by nature monogamous”. Rather, we should be “deliberately promiscuous”, reject domesticity as “an attitude of impotence and hatred masquerading as tranquillity and love” and (again, frequently, like Dean Moriarty) “run away”.

But footloose emancipation on the Greer and Kerouac model has not been cost-free. Greer the libertarian argued that what gets called “rape” is mostly just bad sex, and shouldn’t be severely punished. But the angry and aggrieved women of the #MeToo era seem far from her breezy confidence that bad sex should simply be shrugged off, especially where it feels coercive.

And we’re witnessing a steady re-evaluation of past attitudes to sexual liberation, too. It turned out, in practice, that no sooner was sex liberated from reproduction than it was re-ordered to commerce in enterprises such as the Playboy pornographic empire. Despite Greer’s disapproval of this development, Playboy was for decades a byword for egalitarian, libertine (and commercialised) sexual empowerment. Now a recent documentary has compiled allegations of abuse and even bestiality, by dozens of the Playmates Hugh Hefner brought to live in his mansion. It turns out that the brave new world of free agency and personal responsibility can mesh uncomfortably with real-world imbalances, whether of power, money or beauty.

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Meanwhile, the female sexual emancipation Greer pursued has delivered a bonanza for every live-in-the-moment modern-day Dean Moriarty with the looks to enjoy it. In the world of online dating, sex is even more abundant than it was for Dean Moriarty: one twentysomething friend tells me that “photogenic” male friends find female attention so abundant that some are “quite sick of the attention”.

But not everyone lucks out: among those neither married or possessing the charms to “game” online dating, sexual access may be difficult to come by. And among these “involuntarily celibate” or “incel” men, this uneven erotic liberation has spurred a boiling rage, much of which is directed against women. Over on the other side, too, it’s the other team’s fault: every woman exploited in a #MeToo situation, or running afoul of some other sexual asymmetry, points the finger at “patriarchy” (ie men) for her distress.

But the common factor in both cases is a culture in hock to the libertarianism of Kerouac and Greer. For while this worldview was lionised as freedom, in practice what it delivered was a kind of marketisation of the heart, that imagines we can love according to principles of rational choice and utility maximisation. Rooted in mid-century “liberation”, this paradigm powers much of the hostility between the sexes today.

When a man claims that we shouldn’t empathise with Hefner’s Bunnies as they were adult women who should have known what they were getting into, that’s not “misogyny”. It’s just what it looks like when you apply the market logic of freedom and personal responsibility to sex.

The same market logic suffuses the manosphere fixation on “sexual market value” – and concludes that “West Elm Caleb did nothing wrong”. For in market terms, we’re all independent, rational adults; why shouldn’t a man treat women as human spittoons, should they make themselves available in this capacity?

On the other side of the ledger, we find the same mindset in the women who share “first date evaluation” spreadsheets with their friends; in the supposedly feminist claim that “sex work is work”; or in the bleak assertion that all men cheat, so you might as well hold out for a rich cheater. Or the claim that men’s loneliness is men’s fault, for male loneliness is caused only by “a surplus of high value women and a surplus of low value men”.

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Instead of questioning sexual market liberalism, all we’re offered to make sense of this mess is a schizophrenic “feminism” wholly in thrall to the same fixation on autonomy – but only for women. This worldview celebrates Greer-esque radical autonomy and sexual permissiveness, while dismissing observable normative differences between the sexes as ‘stereotypes’ and blaming any negative side-effects of this approach on patriarchal revanchism.

Beneath this officially sanctioned surface, meanwhile, lurks an increasingly embittered male resentment, that reacts with gleeful schadenfreude whenever a woman acknowledges that there can be tradeoffs between female “empowerment” and motherhood.

Yet neither side is willing to see the field of courtship as anything more than a low-trust, radically individualist, structurally impermanent market – a grim perspective both reinforced and accelerated by the dating apps that now dominate courtship. And under that cloud of suspicion and impermanence, it’s easy to see how the prospect of an 18-year commitment to a dependent child (and hopefully also to his or her other parent) might well seem wildly implausible, or just unattainable.

Where autonomy conquers solidarity, children are psychologically (and, increasingly, literally) inconceivable. But it’s precisely when we get to children that the persistent asymmetry between the sexes becomes most difficult to deny, as poignantly illustrated by the lives of both Greer and Kerouac themselves.

Kerouac is an object-lesson in the wider shock-waves caused when men refuse to move on from sexual hedonism. He married three times, and only grudgingly paid child support for Jan, the daughter he fathered in his eight-month marriage to Joan Haverty after a paternity test. He met his daughter only twice; her life was marked by poverty, trauma, sexual abuse, drug-taking and finally death at 44. Greer, meanwhile, never had children. Her biographer recounts how she struggled and failed to do so, before eventually taking solace in her animals.

Team Kerouac and Team Greer are both really the same camp, then. But depending on your sex, the costs of liberation are inescapably different – and if we just point fingers at the other side’s selfishness, we miss the deeper truth that beneath the pervasive tone of cynicism are real humans of both sexes. And no matter how loudly disappointment curdles to bitterness, nearly all in truth still long for intimacy, companionship and (in most cases) kids.

Such a craving for solidarity is now nigh-on impossible to square with contemporary norms or social infrastructure. Hard as it may be to admit, this is not the exclusive fault of one sex or the other. And yet compassion for the opposite sex’s predicament is ever more difficult to muster.