I met the Worst Boyfriend Ever in New York City.
He wasn’t at all what I expected.
I don’t remember how I discovered his blog, but it was during my first month on Substack. Probably, people were talking about him on my feed — they always are.
If you’re unfamiliar with the Substack drama, WBE writes about cheating on his girlfriend, blowing up his life, then leaving town in a van to travel the United States while taking the virginities of countless girls who message him online.
His stories are unfiltered, stream of consciousness, confessional. He uses innocent-looking cartoon images to contrast the dark themes of self-loathing and sexual perversion.
The blog is a fever dream. It's explicit, transgressive, and undeniably depraved and yet... it captivated me. For a few weeks, it became my shameful secret and guilty pleasure. I read every post.
To be clear, I’m not here to defend the virtue of the Worst Boyfriend Ever. I don't agree with his worldview or abrasive use of language, and I definitely don't align with his core fanbase.
But something in his writing spoke to me.
What was it? Perhaps the crushing honesty and unapologetic expression of sexual desire, however twisted. Or the self-aware drive towards self-destruction. Or, perhaps, the frustrations of being trapped in a dying relationship and the endless demands of social performance.
I think most of us have fantasized, at some point, about packing up and leaving everything behind. But the madman actually did it! Allegedly.
The stories were well written, with strong hooks and great pacing. They were entertaining and occasionally made me laugh — which is rare nowadays.
Were they truth or fiction? Why did thousands of readers, both male and female, find them so compelling? And what was he like in real life? I had to find out.
So when WBE drove the van up to NY, I reached out and offered him a meal. His hungry, homeless ass simply could not refuse.
We met at a café in Midtown, Manhattan.
My first impression: thin, lanky — almost unhealthily so. I guess living in a van for six months will do that to you. Wearing blue jeans, a black jacket, and a grey scarf. About 6 foot. Good looking but not ‘physically gorgeous’ as he’d described himself.
Immediately, he shared his real name. He said there was no point hiding it due to the regular doxings. I pointed out that having such dedicated haters actually legitimized the blog. He agreed.
It was his first time in NYC and I offered to show him around. We walked down Broadway towards Times Square.
He told me about the life he’d left behind. He had been a well-known figure in a community of online gamers, even hosting tournaments for his region. But for years, he lived a double life, unable to express his honest, unfiltered self — except in the Notes app. He’d been blogging anonymously for only a few months before getting exposed, shut out of his old life. Now, his old friends pretend he doesn’t exist.
“I’m like Voldemort to them,” he quipped.
Despite that, he was in good spirits. He was excited about book sales, by the attention he was receiving for his work. He wrote every day, read at live events, and stayed in shape by running regularly.
And weirdly, he was sort of… likeable? He came off as mostly normal, albeit slightly autistic, with a surprisingly childlike attitude. The rampant racism and misogyny that pervaded his writing were nowhere to be seen. Was this really the same WBE?
“I have more of a filter in person,” he explained. “I’m not going to drop the hard R or anything.”
Not around me, at least.
What I wanted to know most was: could I tell?
If I hadn’t read the blog, could I tell what was going through his mind? The sickness, the depravity? If we were complete strangers, could I have seen through him?
I had my answer: absolutely not. I never would have suspected. For someone who railed against the social mask, he wore it well. He knew how to act; he knew what he could get away with saying.
Still, I believe he told the truth.
As we turned down a side street, I asked if he considered himself a sociopath.
“No, I don’t,” he said, “I’m aware of the hurt I cause. I’m able to feel it in others. I don’t think a sociopath would feel that.”
He listed those he’d hurt — girls, his ex-girlfriend, his dad. Not boastfully, but with what seemed like remorse.
I took a measured look at him, then responded with something I’ve told myself many times.
“If you don’t want to be a sociopath, you’re probably not — a true sociopath wouldn’t care.”
I think he was reassured by the lie.
We climbed up a ledge overlooking Times Square, and I asked him why girls were so into him/the blog.
“Because other girls are.” He laughed.
I wasn’t satisfied with that answer. Young women hooking up with a homeless stranger in his van, just because other girls did? There had to be more to it.
Sure, his self-proclaimed, Cialis-powered sexual prowess probably sparks some curiosity. And there is something to be said about the aphrodisiac effect of clout.
But more notably, WBE lays bare — in high definition — the intricate folds of his mind. He writes exactly what he thinks, all the time. It’s private. It’s intimate. Girls who reach out feel like they already know him.
His anonymity fuels imagination — they can project whatever physical qualities they want onto him. His transience means no lasting consequences. He’s the perfect stranger — here today, gone tomorrow. He’s a risk, a thrill, a whispered secret.
That’s my best guess, at least.
Despite his claim of ‘transcending genre’, Worst Boyfriend Ever descends from a literary lineage of transgressive male writers including Delicious Tacos, Charles Bukowski, and Henry Miller. These writers explored male sexuality, alienation, and rejection of societal norms in deliberately controversial ways. As they grew in popularity, so did the number of women who reached out. They never ran out of stories to tell.
I asked about his writing process.
“I take Adderall and write first thing in the morning, every day,” he told me. “I record literally everything I can — every detail, every conversation. Then I come back later and look for the parts that make me laugh, and repurpose those into a story.”
“My goal,” he clarified, “is to make people laugh.”
I asked if he was playing a character. He told me there are two types of writers: those who recognize it’s a performance art, and those who haven’t realized yet.
Stephen King says that all writers are readers, but WBE is the exception. He doesn’t read books, and he doesn’t read comments. But he won’t disable comments on his posts — readers find them entertaining.
“Part of the circus show,” he laughed.
He gave me the impression of someone who thought deeply about his work, who knew exactly what he was after.
Someone who would stop at nothing to achieve it.
“I have nothing to hide,” he told me.
So I asked to look through his Substack DMs. He tossed me his phone.
First, I checked his stats. He had way more views than his subscribers would suggest, which made sense. He said he might have the highest lurk to engagement ratio on the platform.
Then I opened his DMs.
Most of the messages were straightforward: Hey I’m a 19yo college student in NYC, how long are u in town for? A few guys glazing. And, surprisingly, a few accounts I recognized from my feed. I read a couple conversations but felt awkward and handed the phone back without digging too deep.
As I did, a text popped up: cute Asian girl.
“That’s my girlfriend,” he said. “Ex-girlfriend.”
The poor girl he’d written for months about cheating on, whom he’d driven away from in the van… was still on his side, texting him, supporting him.
Somehow, it didn’t surprise me at all.
We got bored and found a basketball court nearby.
It’s been forever since I did this, he said. If you’re wondering, he can’t dribble but he can shoot.1
Then he gave me a ride home in the van.
His passenger seat was filled with junk so I sat on the twin bed built into the back, which was a little… uncomfortable. But honestly it wasn’t that bad. He had soft LED lights running around the perimeter which gave it college-dorm vibes, small drawers for clothes, and a pine tree air freshener that was working overtime. A Psyduck hat lay draped over the passenger seat.
WBE had spent the last half year living in this van. Before that, he’d felt like a pretender, a stranger — but instead of accepting it or adjusting, he drove away. He rejected the social contract, and, in turn, was rejected by society. Now, he drifts between parking lots, showers at planet fitness, and, yes, collects bodies. A lonely, tragic, but liberated existence.
I hopped off the van and waved goodbye. He drove off.
Will his countless parking tickets and traffic fines eventually catch up with him? Will he spiral into maniacal despair in an effort to satisfy his growing audience? Or will the Worst Boyfriend Ever one day rediscover hope and redemption?
Only one way to find out: tune into the show.
I’m not homeless but I am broke so… buy me a coffee
I lost two games of HORSE. He’s not good, I just suck. Hiding my shame in the footnotes.
yo I did NOT realize I had paid comments turned on... thought y'all were just being quiet
the referencing for that reaction pic will never not take me out