How to write a creepy guy for an audience of women

I’m friends with a fair number of guys who’re writing novels about angry losers. And the most talented of these guys, John, was having a lot of trouble selling his book. Agents and editors kept saying it didn’t feel very fresh. It was just the same old story they’d heard before.

“But we haven’t actually heard it!” he said. “There haven’t been any successful novels recently about angry white sexless losers!”

“That’s true,” I said. “Basically they’re just saying they’re not engaged by this story. They don’t care about it.”

“Because they have no empathy for men!”

“I agree with you, one hundred percent,” I said. “But perhaps the problem is your book relies too much on empathy. Like, maybe take a page from O. Henry. He could write about anyone—a bum or a burglar or a greedy millionaire—and it didn’t matter, because the reader trusted he’d do something surprising with the plot.”

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John had given me a copy of his book, The Spartan, for my comments, and I thought it had a lot of promise. Basically, it was about this twenty-five year old Brooklyn-based aspiring writer who was ugly and couldn’t get dates, and who felt embittered because he was apparently so unfuckable.

All it needed, in my opinion, was a few changes to the underlying story. Like…what if, in this novel, you begin with a twenty-five-year old guy who's ugly and poorly-dressed, and the conceit is that he decides to start listing himself on apps as a forty-seven-year-old, because he's heard so much about how the dating market is better for older men.

And the moment he starts lying about being older, this guy is suddenly matching with tons of attractive forty-year-old women.

But the funny thing is, these women are very used to men lying about their age. They know that a forty-seven-year-old man is almost always really fifty-three, just like a guy who says he’s 5’ 10” is almost always really 5’ 7”. So the moment our protagonist, Gary, shows up to these dates, the women realize: Wait a second, this guy lied the other way. He’s just a kid!

A few of the women are upset and cut short the dates, but most are intrigued. They can tell this kid is lonely and lost, but ultimately kinda harmless, so they try and draw him out. They’re happy that this date is somewhat out of the ordinary—that’s if it’s going to be terrible, it’ll at least be terrible in a different way.

And over the course of many dates with these thirtysomething and fortysomething women, Gary learns how to open up and really connect with women. Finally, he somehow talks one of these women into bed, and they have a relationship. In his relationship with this woman, who’s been hurt so much by men, Gary grows up, and he learns how to be a real man himself.

After a few years, this relationship falls apart because…he wants kids of his own, whereas this woman already has two children and doesn’t want any more.

So she sends him out onto the internet, ready to find a match his own age.

And almost immediately he connects online with a thirty-two-year-old woman who seems perfect for him. They have this deep, intimate conversation, where they talk about their feelings of shame and rejection. They've lived an entire lifetime on text before they arrange to meet for the first time. And he realizes that this girl is the one. This is the girl he's going to marry.

But then something terrifying happens. She starts asking if he’s ever been divorced, if he has kids—she confesses she’s never dated someone so much older before. He had forgotten to change his age settings! She thinks he’s almost fifty!

And he wants to come clean, but he knows from their discussion that this girl has major hang-ups about guys lying to her.

But not to worry. He’s got experience with this. He is sure that once he shows up in person, she’ll realize the ruse and be disarmed, and potentially even charmed.

However, since he really cares about this woman, he wants to be presentable, so he gets a haircut, gets his beard professionally barbered, and goes to buy some new clothes. He tells himself that he’s grown up. He’s not an ugly loser anymore. He’s spiffy and presentable—a real man, someone whom any woman could love.

And then he shows up at the bar to meet his match.

But this woman in the corner, scanning the room—well, the moment she sees him, she gets a really weird feeling. This guy isn’t in his late forties—he is, at most, thirty years old. But he’s well-dressed and has a confident stance. What the fuck is wrong with him? Why is he pulling this bizarre trick, lying about his age? She was already a little bit suspicious, because this guy seemed way too good to be true. But now she knows for certain: there is something deeply wrong with him. And she's had terrible experiences in the past, so she knows that in New York there's no such thing as a hidden gem—there's always a catch.

She ghosts him. Just walks out, unmatches, deletes his number.

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After getting my comments, John said, "Okay...and to you this would be a good story?"

"Yeah," I said. "It's got the essence of your novel, but it's fun."

"I disagree," he said. "It's...it's hacky…it’s stupid. It’s basically just a rom-com with a slight twist.

“More like women’s fiction, but yeah,”

“It's dishonest. I’m sorry, but it's just not my book.”

"Okay. Good. Thank God. Because I wrote up three chapters of my version, under the title The Older Man, and sent it to my agent—she’s talking to editors and they seem pretty excited. A few have asked if I'd consider giving the character a happy ending, but I keep saying no, he doesn't deserve it.”

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P.S. Neither John nor his book really exist! This is just a story—a tale directly inspired by O. Henry’s story “The Poet and the Peasant”.