We all know the literary lothario. From Norman Mailer to Martin Amis and beyond, young men of letters have long done double duty as heartbreakers. Now, in her first published novel, The Love Affairs of Nathaniel P., author Adelle Waldman turns the classic amatory account on its head—the randy titular writer isn’t just written by a woman, he’s conflicted about mistreating women. Well, kind of.

The buzzed-about book follows young Ivy League-grad Nate through a whirlwind of Brooklyn dinner parties, coffee shop writing sprees and the highs and lows of newfound success. And while he manages to burn through a bevy of bookish babes along his way, Nate’s got that 21st-century sensitive thing going on, giving him more hem-and-haw than Hemingway.

Waldman spoke to DuJour about creating the character, the five years it took her to write the book and who the inspiration behind her heartbreaking hero truly is.

Where did the character Nathaniel come from?
About five years ago, it started as a lark. I had this idea—I was thinking about books and smart men who come to New York City to conquer it with their intellect and romantic adventures—and felt like I could write a character like that, but take him to task for how he treats women. It felt like a dare and like I should really do it.

It seemed too easy and fun to be a real idea for a novel. I had written one other novel that I finished and didn’t get published, but I loved writing it. I knew I wanted to do it and I had been able to write a novel with a beginning, middle and end, but I’d never published a word of fiction. That’s where I was in my life.

What was the most challenging aspect of writing the book?
Because he was a man, I couldn’t use the main character as a stand-in for me, to vindicate myself or to make certain points. I had more perspective on him. That was really liberating. But the flip side was I couldn’t draw on my own thoughts. I had to work out what Nate would think about every little thing. Luckily, there was some overlap as we have similar interests.

The young man who’s come to master the great city is a sort of classic story, but you’ve updated it for a new generation.
I tried to draw on my experiences with people in the world. For the character today to be who I wanted him to be, he almost had to live in Brooklyn. It wasn’t working from other books so much as working from the social milieu I know and trying to reflect reality. At the same time I tried to be careful not to use too many proper nouns—like neighborhood names or restaurants—but I wanted to be sociologically accurate.

You said that you wanted to hold Nate accountable for his actions, but he’s not the only one. The various ladies in his life don’t get off so easily.
As much as I thought it would be neat to take this guy to task, I didn’t want to do this thing women, including myself, sometimes do, which is discussing some guy who hasn’t behaved in the way you wanted and just saying, ‘What an asshole.’ I wanted to complicate things; the male character has his reasons to do what he does, but the women are not perfect and virtuous at all moments. There had to be some fairness, I didn’t want to seem as if I was creating this character to humiliate him.

Is Nate different from the literary heartbreakers who’ve come before him?
There’s this point in the book when Nate thinks to himself about Bellow and Roth and Mailer and he wishes he could be as cavalier about women’s feelings as they were, but he can’t be. To me, that was important because I do think there’s a generational change. I wanted to write about a world I know: I don’t think it’s perfect but I don’t think it’s horrible. The women in the book don’t have a great time, but it’s different from the world that came before.

There will be inevitable mentions of Girls when people discuss your book, which is also about smart, conflicted young people in New York City.
One of the challenges for me in writing this book was to try to make it so the characters can resonate and be interesting even for people who don’t care about my little world. A danger for a book is to be only of interest for it’s non-literary components, so I wanted to use this world because it’s a world I already knew, but I hope I didn’t rely too heavily on inside jokes and that kind of thing.

There’s already some speculation flying about who these characters are based on.
If anyone thought I was stealing their life, they’ve not told me so. I have definitely heard various theories about how so-and-so character reminded them of someone and it’ll always surprise me. My mother didn’t like the portrayal of the mother in my previous novel and it was genuinely upsetting, so I was really careful in this one. I tried to avoid actual people who’ve ever confided in me about their lives.