A Horny Unkillable Shadow

How Worst Boyfriend Ever’s success was inevitable.

This piece is free to read without a subscription.

---

Every criticism I’ve read of Worst Boyfriend Ever (WBE) disparages his moral character and paints him as a sociopath. They demand that he be beaten by the good men of our society, that he be punished for his violations of common sense morality, or that his work wholly fails as art. Sometimes, they engage in armchair psychoanalysis to piece together his vile behavior and misogyny, arguing that he’s watched too much Neon Genesis Evangelion for his own good and that he’s trapped in a pick-me phase he won’t grow out of. They say that if he wants to write anything of literary value, he needs to read real literature about people who hate themselves like Dostoevsky’s Notes from Underground or Philip Roth’s Portnoy’s Complaint.

Pervading these criticisms are disbelief about how this person’s writing has garnered a cult-like following, and perhaps a disappointment at how far literary culture has fallen if this is what attracts readers. We don’t want him to exist for a myriad of reasons: he violates our idea of what kind of literature deserves attention, of our progressive sense of morality and justice, of how we want men to behave in our society. He incites a kind of madness in his critics who all, apparently, want him dead in a ditch.

I don’t disagree with these criticisms, but I also think they miss the point. The issue is that he does exist. He is alive and well, thriving in fact, in the 25 Top Fiction Substacks at time of writing, rubbing shoulders with established writers like Etgar Keret and Chuck Palahniuk. But if we move past his shock factor, it becomes much, much more interesting to examine what his popularity is a symptom of. It makes perfect sense that, against our literary and moral instincts, WBE has found success: he’s the only notable person writing honestly about being an average young man in 21st century America. He is the Jungian shadow of American masculinity.

Readers of Jung know that to deal with their shadow, or the repressed parts of themselves, they must integrate it into their self-conception in a healthy manner. To ignore the shadow leads to conflict with oneself and to inevitably project that conflict onto others. WBE crawled out of this shadow. It was the cultural suppression of masculinity in the well-meaning era of Obama-style progressivism and the MeToo movement that created the conditions for him to exist. He is the mildest misogynistic thought mutated a thousand times over. He is infection turned sepsis, the cancer we wanted to cure by shouting feminist slogans until it disappeared.

But there is something good about him—he makes the ugliest parts of the ordinary man, of American masculinity at large, visible. And we cannot hope to change something we refuse to admit exists.

---

In the 2010s, our culture attempted to hold men accountable for their vast abuses of power in every corner of society. With good intention and reason, the liberal left attempted to dismantle patriarchal power, vengefully demanding not just that powerful, abusive men answer to justice, but that all men had better adjust their behavior or else face the consequences. Thus began the campaign to publicly shame masculinity into non-existence. Men were told to abandon their values and to stop taking up space without really understanding why, only knowing that it was no longer appropriate to express certain perspectives or worldviews. Misogyny, racism, and masculinity, it was loudly declared, no longer have a place in our culture.

But shaming something is not the same as addressing it. To shame something is to stuff the monster into the basement, and anyone who’s ever been ashamed knows that monsters thrive in the dark. Shame is a useful tool of social control insofar as it forces someone to adjust their behavior in public, but it does nothing to address the underlying emotions and beliefs at the root of such behavior. Intellectually, it’s easy enough to understand why misogyny and racism shouldn’t exist, but the work of changing one’s beliefs is much trickier, much more laborious. It’s difficult to imagine that men are reading bell hooks or Simone de Beauvoir or having genuine conversations about the misogynistic beliefs they were invariably raised with. (With whom would that happen? Their parents? Their girlfriend? A male friend? I highly doubt it.)

We can see a parallel in our attempts to make our society less racist. The sudden uptick in media representation of POC, DEI policies, and affirmative action did not make our society more accepting of others. It just led to people hiding what they actually think while doing what was expected of them. The demand for public accountability put us into a panopticon under which, yes, people could no longer express racist and misogynistic thoughts, a good thing surely, but that also shut down genuine attempts to engage with problematic beliefs. With the gun of social exclusion held to your head, it’s much easier to simply nod along, loudly proclaim you are an ally, and bolt shut the basement door.

WBE, then, lets the monster out to play. He embodies the average man we so badly wanted to have slain in the zeal of 2010s progressivism. His exploits resurrect the American mythology of masculinity that men were taught to suppress a decade ago: what man hasn’t dreamt of quitting his 9-to-5 to wander across America in a van in a quest to become his own master? What man wasn’t socialized to believe that fucking prodigious amounts of (foreign) women would increase his value as a male? Most recently, what man hasn’t fantasized about acquiring wealth through a mix of cunning and sheer luck, perhaps through a crypto rug pull?

It doesn’t actually matter if the Substack is fictional or not. The writing feeds the juvenile male fantasy for a Hero’s Journey full of risk, irresponsibility, adventure, drugs, sex, and other social transgression. Because he’s quit his job and because the liberal left don’t have a stomach for violence, WBE has effectively made himself untouchable. He cannot be canceled because the consequences of cancellation have no effect on him. And so, in a time of moral fingerwagging, performative men read him with secret glee. WBE reminds his readers that it feels good to be bad.

Of course, if these misogynistic, hypermasculine exploits were all he wrote about, WBE would not nearly have gained this amount of traction. One can only be so entertained by male braggadocio and barely perverse erotica. His greatest narrative trick is interspersing his work with genuine moments of his humanity. In his writing are honest, if undeveloped, glimpses of the indomitable human spirit, of Kierkegaard’s knight of faith or Nietzsche’s Übermensch, that speak to the self-fulfillment that all Americans have been trained to want. There is something seductive to watching someone completely self-destruct in the pursuit of absolute freedom and actually getting it. He is Jack Kerouac for the porn-brained, social media-crippled generation, Hunter S. Thompson filled with microplastics and Adderall. Even in the dehumanizing prison of late capitalism, he renews the average young man’s faith that he can find himself on his own terms.

More importantly, his writing is framed outside of any political ideology and rejects any kind of moralization. It’s obviously not feminist or leftist, and he doesn’t show support for any type of red pill or incel movement (although that’s what his actions essentially amount to). He’s not a white Christian nationalist or a groyper and most likely doesn’t wish for a boogaloo. He seems only to say: This is what I do. It makes me feel free and I’m happier than I’ve ever been. Men in America are easily seduced by the idea of radical transformation into someone freer, stronger, and in some vague but very profound way, better, and in an era where men have drawn contempt for simply existing, WBE is music to their ears. For rebellion against social norms, he was rewarded with self-actualization. Nothing is more tantalizing.

All of this is complemented by his confessional, typo-ridden prose style. In terms of literary merit, his writing will fail when judged on the aesthetic grounds of traditional prose. As many critics have stated, it’s just not very good stuff. But the unedited, poorly punctuated writing lends him plausibility, makes him emotionally and literally legible to everyone, including men who don’t read. He feels real because his posts are what we would write down in our Notes app after a bad hook-up or after ruminating in the dark for too long. He is the person we’ve all been at some point in our lives, standing in the corner at some party where we don’t know anyone and, feeling insecure, types something disdainful about the people around us into our phone.

Frankly, the average man won’t want to read his literary equivalents like Ben Lerner’s Leaving for Atocha Station or John Updike’s Rabbit, Run. But people do want to read quick, snappy texts and half-finished blog posts about a guy who exits the rat race and fucks Asian women in his van in every city across America, and then wonder why on earth he feels sorry for himself after. Although those novels and the Substack cover the same exact subject matter, at face value, WBE is much more interesting. He’s been savvy, too, by playing to the Substack platform’s strengths and making the readers who interact with him part of his project. Women can reach out to him and fuck him and men can buy him plane tickets to the Phillippines and take him to strip clubs. In doing so, he’s made it a choose-your-own-adventure text, where readers can literally write themselves into the work and get a taste of his freedom and internet fame. What we end up reading are the confessions of a free yet broken person, a timeless subject, but rendered legible to the chronically online.

Social transgression, informal existentialism, resistance to moralization, casual writing style, reader interactivity: together, these elements have made him popular beyond belief. And underpinning his success is the cry of a male who no longer understands his place in society but wishes for recognition as a fully-fledged person. This is, on some level, what every young American man has felt deprived of over the last decade. It’s almost enough to forgive him.

---

One only needs a modicum of critical thought to see that the man is deeply unwell. Readers of WBE know his gimmick: immediately after (and sometimes during) a despicably selfish act, the circus of self-awareness begins. By engaging in the requisite histrionics of being a fuck-up, by complaining about his loneliness, by performing any number of existential theatrics to explain his terrible behavior, he attempts to evade accountability. He wallows in his identity as a “sensitive young man,” wants you to feel that same cloying pity you felt for Shinji on your first Evangelion watch as a seventeen-year-old. And like that abstract final episode, he wants to be applauded by all the people he’s hurt on his journey to finding himself. In reality, he hasn’t even gotten in the robot—he hasn’t taken responsibility for the harm he’s caused. But that’s all fine. At the end of the day, he’s just a rascal with a heart of gold. Really!

I imagine there’s something about this claimed innocence that resonates with his male readers. Underneath all their awful behaviors and masculine posturing, they are “just” a person trying to figure themselves out. It was this innocence that the 2010s hunted down and attempted to stamp out. And generally, men complied, quickly understanding that to question this jarring shift in behavioral standards meant to admit wrongdoing, to admit misogyny. It would be social suicide. But it’s exactly this suppression of the male psyche that brought WBE to life. His writing gives men permission to be men again, in all their grotesque and juvenile glory.

This isn’t necessarily a bad thing.

WBE’s presence undoes the shaming of masculinity, which in turn frees our culture to appropriately address its more toxic aspects. As stated previously, we cannot change something we refuse to admit exists. You cannot kill the monster in the basement without opening the door. For better or worse, his blog holds a bright and shiny mirror up to American masculinity, reminding us that these types of thoughts can exist in the ordinary men around us not because they think it’s right, but because it was the culture they were raised in. We must recognize the difficulty of changing one’s beliefs and the impossibility of shaming someone into doing so.

In the words of bell hooks, “To create loving men, we must love males.” It’s unfortunate how bell hooks has become a faux pas of performative maleness, because it would do our culture well to look at masculinity carefully and clearly and figure out how to make it work. We’ve seen what happens when we cast men out of mainstream culture, even if for good reason.

So let the goblins out of their dungeon. They need to breathe air, feel sunlight, remember what it’s like to speak with words, not with grunts and gnashing teeth. Let them find genuine, healthy community with other men. Let them question things in good faith even when it makes you wince. Let them befriend women so that they may soften. Exercise both caution and compassion and hold them accountable, not out of vengeance, but because you believe in a better world.

Ultimately, there is a reckoning coming for WBE. Whether it’s someone getting sick of his antics and committing a real act of violence against him or whether he undergoes a spiritual awakening that compels him to end his blog, he cannot sustain this life forever. The mythologized freedom that he sought by self-destructing has no actual end game. He knows this. But I do believe he should keep writing. We get to read and watch him live out our adolescent dreams so we don’t have to. And when his story ends, one way or another, we can finally grow up and move on.

---

Behind the Scenes

As part of our commitment to keep all our essays and stories free, we ask our authors to pull back the curtain and share a little bit about their writing process and intent as a bonus for paying members.

You can find an explanation and reflection from the author of this piece just below…