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Teddy Wayne on The Winner photo

Sexy tennis love triangles are trending this spring. And I'm not just talking about Challengers. Teddy Wayne's sixth novel The Winner also stars hot people using tennis as foreplay. The novel begins with the handsome Conor O’Toole arriving in Massachusetts for the summer to teach tennis while studying for the bar exam. In exchange for giving lessons, he enjoys free lodging in a swanky guest cottage in Cutters Neck, a fictional Cape Cod community where the uberwealthy take refuge from the pandemic. A far cry from his mother's cramped apartment in Yonkers, it's a cushy gig until an acerbic divorcée approaches him for lessons—and more. Soon, he’s earning more money than he’s ever seen for sex with a woman twice his age. Complicating matters, he meets a captivating and age-appropriate woman on the beach whom he can't resist seeing. Conor works tirelessly to manage this tangled web—until he makes a tragic misstep he can’t undo. I read this book so fast my eyes started to burn. Read my convo with Teddy below.

The Winner stars a tennis player—do you play? 

Yes, but I peaked at 15 and was never as good as Conor, the protagonist who played in college and makes ends meet as a tennis pro. He’s a “pusher,” a defensive player who hits conservatively and seldom makes a mistake. I’m somewhat like that, but more of a junkballer, a term better known for baseball pitchers: someone who gets by with unexpected spins and slices and wiliness due to a deficit of conventional talent.

Your books are brilliantly paced and plotted, this one in particular—do you outline? What’s your secret? 

I do outline, especially this one, which required more intricate plotting than any of my previous books. I start with a very vague idea of character, story, and setting, and begin writing blindly to get a sense of voice and make sure it’s something I want to pursue. Once I’ve written at least a few pages and have committed to it, I outline a three-act structure with a midpoint, to give myself the broad contours of a beginning, middle, and end. I fill in the major plot points, then the moments between those points, trying to make them as causal as possible—scene A causes scene B causes scene C—and so on, until I have something close to a detailed outline. Then I give myself latitude to shift around and revise that outline as I discover new things during the writing process.

I see that The Winner is in development for a feature film adaptation—what’s your dream casting?

There is—currently, at least—an actor attached to play Conor whom I can’t name. I probably therefore shouldn’t name any other contemporary actors. So let’s go with a young Matt Dillon for Conor, a young Michelle Williams for Emily, and a middle-aged Faye Dunaway for Catherine.

The main character is a law student and there is a lot of law in the book, particularly towards the end—did this require a lot of research? 

It required me frequently texting an assistant district attorney I know, an NYPD detective I know, and my lawyer sister-in-law. The assistant DA gave me endless information about criminal law and an idea for a major twist in the book; the detective walked through what the police would be thinking and doing at every step in the book and what a smart criminal might do; and my sister-in-law gave me plenty of answers about the mundane matters of being a law student and recent graduate taking the bar and applying to jobs.

What’s your favorite time and place to write?

I prefer to work at home. I’ve got two young children who usually get out of school by 3 p.m., so it has to be before they start wreaking havoc. Right now, as I type, they both just got home, one is crying, and my workday is pretty much over.

If you were a literary critic, what would you say about your writing? 

“The junkballer of novelists.”

Where’s your dream writing retreat?

A hammock, a pot of fresh coffee, a secluded cabin, and—kidding. I’ve been to some writing retreats, and while they’re certainly pleasant, I’ve also found being in the middle seat on a cross-country flight can be the most productive writing session of all.

What are your most overused words?

I’m not sure, but whenever I finish a book, I try to find a program that gives me the total word count for specific words (beyond common ones like “the” and “and”), to make sure I don’t overuse them, and I can never find a good one. If anyone knows of such a program, please let me know.

What’s a book you wish you’d written? And/or a book that made you want to write? 

It’s embarrassing to say as a person in his forties, and I haven’t reread it in years, but The Catcher in the Rye remains the book that made me want to become a writer and probably the one I wished I’d written (maybe a tie with Lolita).

What author’s (dead or alive) persona is aspirational? 

It’s not necessarily aspirational, because I think few of them were very satisfied with how it turned out, but I’d like to become/possibly am becoming one of those jack-of-all-trades writers in the ‘60s and ‘70s—such as Terry Southern—who bounced around between novels and screenplays and whose tone and subject matter tended toward the satirical and social. Even with Southern—celebrated for both his novels and screenplays—they lose their prime novel-writing years to chasing Hollywood money and glitz, are chewed up and spat out by the film industry, and their books are mostly forgotten about afterward (their movies have a better chance of sticking around). So, again, not really aspirational.

Favorite recent read? 

I’ll have to name my wife’s, Kate Greathead, forthcoming second novel: The Book of George.

What’s one word to describe what you’re working on now?