Outrage, Anxiety, Prurience: the Woman Who Had Sex with 100 Men in One Day and Why We Can't Stop Talking About Her

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The week belonged to two Gen Zers, Daniel Penny and Luigi Mangione, whose respective acquittal and arrest have spawned thousands of thinkpieces. Yet in the last 48 hours, a rival (and even younger) distraction has emerged: Lily Phillips, a 23-year-old Englishwoman and Only Fans model. Phillips stars in a just-released YouTube documentary, entitled I Slept with 100 Men in One Day. Since yesterday, everyone and their llama is writing and fretting about the documentary, and what it apparently reveals about our sick, misogynistic, sin-fettered modern world.

(The documentary itself is not pornographic. If you want to see more of Lily Phillips, her explicit material is easy enough to find. It also has no subtitle, which means the documentarians do not work in American publishing. If you have an academic background, you can amuse yourself endlessly by coming up with ever more absurd titles. I Slept With 100 Men in One Day: Mapping the Margins of Misogyny, Misery, and Masturbatory Misuse. That sort of thing.)

Miss Phillips

Lily and her team are first-rate provocateurs, and the American media has taken the bait. Even the Free Press, the immensely successful website established by refugees from the New York Times, couldn’t resist. Yesterday, they posted a now-viral article whose title asks What Does Sleeping with 100 Men in One Day Do to the Soul? You’ll be disappointed to know that despite posing a theological question, the Free Press does not offer much of a theological answer. Instead, there are a lot of presumptions.

“It’s intense,” Lily says, looking despondent, her makeup washed off.

“More intense than you thought it might?” Pieters (the documentarian) asks.

“Definitely,” Lily says, breaking down. “I think it was like. . . feeling so robotic.” She wipes tears from her eyes. “I’ve got this routine of how we were going to do this, and like sometimes you’d just dissociate and. . . it’s not like normal.”

In other words, she endured her ordeal by separating her body from her soul.

“In other words,” is doing a great deal of work. That last hyperlink takes you to a Psychology Today article on dissociation, which describes mentally detaching from reality. Detaching from reality is, um, not quite the same thing as “separating body from soul.” The Free Press is using moral and spiritual language to draw in readers, but lacks the gumption to back it up by doing anything more than make a relatively anodyne observation about dissociation. It’s a bait and switch.

The Free Press has become famous as a beachhead for heterodoxies. It was founded by Bari Weiss, who resigned from the opinion pages of the New York Times in the convulsive summer of 2020. As you'll remember, that summer was the moment of “Peak Woke” following the death of George Floyd, and the mainstream media (and countless other public institutions) were engaged in an extraordinary frenzy of self-flagellation. The preferred term was “long-overdue reckoning,” but whatever you called it, there was a dramatic and unprecedented lurch to the left on the part of the legacy media. Weiss was one of many who thought that lurch was reckless and extreme, an overreaction to the recklessness and extremism of Donald Trump’s first administration. She started the Free Press as a refuge for classical liberals, the sort of readers and writers equally appalled by the hysterical pieties of cancel culture and by the puritanical provincialisms of the religious right. Someone had to stand up for free speech, free minds, free markets, a free press – and when it came to more intimate matters, an indulgent attitude towards free love.

That appeal struck a chord with me. I was an early subscriber to the Free Press, and still am. The problem, however, is that when you are a very consistent sort of liberal, tolerance is reflexive. It is also very boring. It doesn’t draw clicks. The moment people complain about others having too easy an access to something they “shouldn’t” – like pornography, or guns – the classical liberal response is to defuse the outrage and preach some pluralist platitudes. You can’t draw advertisers and sell subscriptions by insisting on tolerance. People enjoy being outraged. They take pleasure in being upset. They want to send a link to their friends, adding the comment, “Can you believe what the world is coming to?”

If there’s money to be made still in journalism, it’s in anger and it’s in advocacy. And so, the Free Press is now willing to follow the rather illiberal strategy of fretting about the damage that sex work does not only to the psyche but to the soul. Donald Trump may be shy about the specifics of his faith, but those who surround him do not have that same reticence. They are quite clear, in many instances, that they see unfettered access to pornography as a grave moral crisis. They have a vested interest in getting ordinary folks riled up about the scandalous excesses of a depraved age. From a purely mercenary standpoint, in late 2024, it makes sense for a secular liberal publication to start worrying, very publicly, about the souls (and not just the working conditions) of pretty young women.

So that’s why the Free Press used this particular framing. What of the other issues the Phillips story raises?

One is censorship. As someone still fairly committed to a very dated understanding of liberalism, and as a free speech absolutist, I do not want a world where either Lily Phillips or any of her 100 partners are subject to arrest. I do not want a world where it is illegal for adults to view sex acts between consenting adults in the privacy of their own homes. I worry a good deal less about the harm that pornography does to the psyche than I do about the harm that will be done by an electronic surveillance state sufficiently powerful to stop the viewing of porn. That’s a classic libertarian answer, and it is a flawed one, because when it comes to complex moral questions, all answers are flawed. We must choose the least bad option, and that generally means tolerating the proliferation of what some consider a vice out of a well-founded fear of giving any authority the power to stamp out that particular vice.

(A side note. The Daily Mirror chose this terrific headline, driving home the point that for our British cousins it is the middle-class — the staid bourgeoisie — whose offenses against the sexual order are somehow worse than those committed by either the workers, who can’t be counted on to know better, or the aristocracy, for whom depravity presumably comes with the title and the country house.)

Another issue, of course, is the distinction between toleration and celebration. It’s one thing to say that Lily Phillips should be allowed to have sex with 100 men on camera and sell the tape. It’s another thing to shrug and say, “Gosh, that’s a healthy choice.” Of course, we regularly depict incredibly unusual feats of endurance, confident that most will not be tempted to repeat it. Just because I sat with my kids to watch Alex Honnold free solo up El Capitan does not mean I want either Heloise or David to try to imitate him. We come from a family of climbers, and we have one famous mountaineering death in our history. Risk and loss are part of our people’s lore. I told the kids “Your father would be ill if you tried that.” I added, “And of course, I couldn’t watch.”

Mr. Honnold

I imagine Lily Phillips’ papa had a very similar sentiment to my own.

I pushed my body to extremes too. I ran many races when I was younger. 5Ks turned into 10Ks, and marathons turned into ultras. After every ultra-marathon I ran, I got very sick. I have finished day long races on my hands and knees. I once had diarrhea at the end of a race and soiled myself. Two other times, I needed IV fluids. I had dizzy spells weeks after my last ultra, and a cardiologist told me that I needed to quit long-distance running. My left ventricle was disproportionately and dangerously enlarged. I had started running for my health – and I quit for the same reason.

As I went from marathons to 50Ks to 50-milers, people would say to me, “I can’t imagine running that far.” I would shrug with pride when I heard words like that. I liked being different. I liked being tough. I liked proving my toughness even when it meant I shit myself before the finish and endured weeks of subsequent syncope. I cried from pain after races. If you’d had a documentary film crew making a movie about me, they could have painted me out as a torture victim rather than a willing and enthusiastic participant. They could easily edit out the pride and the endorphin high that was so exhilarating. I suspect that for Lily Philips, these enormous numbers of partners are painful and shattering, as anything that pushes the body to the limit can be painful and shattering. My point is simple: it’s good to be cautious about misreading tears as proof of misery and regret.

Am I really comparing sex work to ultrarunning? Unlike most people, I’ve done both. They are different, but they do both blur the line between pain and pleasure, between what is a compulsion to exorcise demons (a spiritual allusion) and what is done out of a joyful, contrarian stubbornness to do what everyone else says can’t or shouldn’t be done.

The Lily Phillips documentary is not going to usher in an epidemic of young girls trying to best her dubious mark, just as Alex Honnold’s documentary did not lead to very many free-solo assaults on the great granite slabs in Yosemite national park. We forget that most people have a fairly sturdy blend of healthy fear, common sense, and an awareness of their own physical and emotional limits. We can gaze with lust or disgust (or anxiety, or awe) at things that astonish us without any chance that we’ll attempt to imitate what we see.

If theologians wish to have a serious debate about what sex work might do to an immortal soul, that would be interesting and welcome. I haven’t seen that with Lily. Instead, I’ve seen a lot of people taking their daily dose of outrage, greedily sucking in that sweet, syrupy indignation, fiending and fulminating on their sugar high of umbrage. As a good laissez-faire pluralist, I’m not gonna tell you to stop. I will ask, in my best casual youth leader voice, “So – how’s all this working out for ya?”